WO2003078405A1 - Parasiticidal agents - Google Patents

Abstract

The invention relates to the use of N-cyanoaryl-nitrogen heterocycles, substituted acylaminophenyl-uracils and substituted aminophenyl-uracils for systemically and non-systemically controlling parasites on animals and in their surroundings.

Description

Parasiticides

The present invention relates to the use of N-cyanoaryl nitrogen heterocycles, substituted acylaminophenyl uracils and substituted aminophenyl uracils for the systemic and non-systemic control of parasites on animals and in their environment.

N-cyanoaryl nitrogen heterocycles and their herbicidal properties have been described (cf. WO 91/00278, DE 42 37 920, EP 408 382 / US 5 084 084, EP 438 209, EP

473 551). WO 95/29168 describes herbicidal N-cyanoaryl nitrogen heterocycles which also have an insecticidal action. The control of parasites on animals or in their environment is not proposed.

Substituted acylaminophenyl uracils (cf. WO 00/02867, EP-A-408 382 / US-A-

5 084 084 _. / US-A-5 127 935 / US-A-5 154 755, EP-A-563 384 / US-A-5 356 863, WO-A-95/29168, WO-A-96/35679, WO- A-97/01542, WO-A-97/09319, WO-A-98/06706) and their herbicidal activity (cf. WO 00/02867) are known.

It is also known that certain substituted aminophenyluracils have herbicidal and insecticidal properties (cf. EP 408 382 / US 5 084 084 / US 5 127 935 / US 5 154 755, EP 563 384, DE 44 12 079, WO 96/35679). However, these compounds have so far had no significant significance as herbicides or as insecticides. There is also no reference to the use of these compounds for controlling parasites on animals or in their environment.

Surprisingly, it was found that N-cyanoaryl nitrogen heterocycles, substituted acylaminophenyluracils and substituted aminophenyluracils are suitable for systemic and non-systemic control of parasites on animals and in their environment. , Indation affects connections

of the formula (Ii)

in which

R ^{1 represents} hydrogen or halogen,

R> 2 represents the grouping below,

\, SO ₂ -A ¹ N ²

(A ² ) _n -A ³

wherein

n represents the numbers 0 or 1,

A ¹ represents optionally substituted alkyl, alkenyl, alkmyl, cycloalkyl, cycloalkylalkyl, aryl arylalkyl, heterocyclyl or heterocyclylalkyl,

A ^{2 represents} alkanediyl (alkylene), and A ³ for formyl or for an optionally substituted alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulfonyl, cycloallcylalkylsulfonyl, arylcarbonyl, arylalkylcarbonyl, aryloxycarbonyl, arylsulfonyl, heteroalkylsylsulfonyl or heterocylsulfonyl or

R represents hydrogen, halogen, cyano or optionally substituted alkyl,

R ^{4 represents} optionally substituted alkyl or

together with R ^{3 represents} alkanediyl,

Z represents one of the groupings below

worm

R represents hydrogen or in each case optionally substituted alkyl,

Alkenyl, alkynyl, alkylcarbonyl or alkoxycarbonyl, or stands for A ino or hydroxy (in each case only bound to N),

or

(ii) of the formula (Iii)

in which

Q represents oxygen or sulfur,

R ^{1 represents} hydrogen, cyano or halogen,

R ^{2 represents} cyano, thiocarbamoyl, halogen or optionally substituted alkyl,

R ^{3 represents} in each case optionally substituted alkyl, cycloalkyl, aryl, arylalkyl or heteroaryl,

R represents in each case optionally substituted cycloalkyl, aryl or heteroaryl,

R represents hydrogen, halogen or optionally substituted alkyl or alkoxy,

R represents optionally substituted alkyl and

R represents hydrogen, hydroxyl, amino or optionally substituted alkyl, alkoxy, alkenyl or alkynyl, or

(iii) of the formula (Iiii)

in which

n represents the numbers 0 or 1,

A stands for optionally substituted alkanediyl (alkylene) or cycloalkanediyl, or - with the proviso that n stands for 1 - also stands for a single bond or is linked to Ar via an alkanediyl group,

Ar represents optionally substituted aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (alkyl),

R ^{1 represents} hydrogen, amino or optionally substituted alkyl,

R ^{2 stands} for carboxy, cyano, carbamoyl, thiocarbamoyl or for optionally substituted alkyl or alkoxycarbonyl,

R ^{3 represents} hydrogen, halogen or optionally substituted alkyl, R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,

R ^{5 stands} for cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl or alkoxy, and

R ^{6 stands} for hydrogen or for optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkmyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, arylalkylcarbonyl, arylalkylsulfonyl, heterocyonyllyl carbonyl

to fight parasites on animals and in their environment.

The compounds of formula (Ii) and their preparation are described in WO 95/29168 and in US 5,759,957; reference is hereby expressly made to these two documents.

According to the meaning of Z, the formula (Ii) represents the isomeric compounds of the general formulas (IiA) and (IiB) below

Preferred compounds of the formula (Ii) are those in which R represents hydrogen, fluorine, chlorine or bromine,

R represents the grouping below,

wherein

n represents the numbers 0 or 1,

A ^{1 represents} a radical of the series alkyl, alkenyl or alkynyl, each optionally substituted by halogen, cyano or C ₁ -C ₄ alkoxy, each having up to 10 carbon atoms,

A ¹ furthermore represents cycloalkyl or cycloalkylalkyl with 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, each optionally substituted by halogen, cyano or C 1 -C 4 -alkyl,

A ¹ furthermore represents in each case optionally substituted by halogen, cyano, nitro, carboxy, carbamoyl, by Cι-C ₄ -alkyl, C - alkoxy, Cι-C ₄ alkyl thio, C ₁ -C alkylsulfinyl or C - Alkylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), by dimethylaminosulfonyl or diethylaminosulfonyl, by C 1 -C 4 alkoxycarbonyl (which is optionally substituted by halogen, methoxy or ethoxy), by phenyl, phenyloxy or phenylthio ( which are each optionally substituted by halogen, cyano, methyl, methoxy, trifluoromethyl and or trifluoromethoxy) Aryl or arylalkyl having 6 or 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part,

A ¹ for each optionally by halogen, cyano, nitro, carboxy, carbamoyl, by C 1 -C ₄ -alkyl, C 1 -C ₄ alkoxy, C 1 -C ₄ alkylthio, C 1 -C ₄ alkylsulfmyl, C 1 -C ₄ alkylsulfonyl or C ₁ -C alkoxy carbonyl (which are each optionally substituted by halogen), by phenyl, phenoxy or phenylthio (which are each optionally substituted by halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C haloalkyl, CC ₄ - Alkoxy and / or CrC ₄ -haloalkoxy are substituted) substituted heterocyclyl or heterocyclylalkyl having 2 to 6 carbon atoms and 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the saturated or unsaturated heterocyclyl part and optionally 1 to 4 carbon atoms in the Alkyl part stands,

A ^{2 represents} alkanediyl having 1 to 4 carbon atoms, and _<

A for formyl or for alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl each optionally substituted by halogen or C 1 -C ₄ -alkoxy, each having up to 6 carbon atoms, for cycloalkylcarbonyl optionally substituted by halogen, cyano or C 1 -C ₄ alkyl, Cycloalkylalkylcarbonyl, cycloalkylsulfonyl or cycloalkylalkylsulfonyl each having 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, or phenylcarbonyl, naphthylcarbonyl, phenylmethylcarbonyl,

Naphthylmethylcarbonyl, phenoxycarbonyl, naphthyloxycarbonyl, phenylsulfonyl, naphthylsulfonyl, phenylmethylsulfonyl, thienylsulfonyl, pyrazolylsulfonyl, pyridinylsulfonyl or pyridinylmethylsulfonyl (each of which is optionally substituted by halogen, cyano, C 1 -C 1 -C 4 alkyl) _. Haloalkyl, -C-C ₄ haloalkoxy or

CrC ₄ - alkoxycarbonyl are substituted), R ^{3 represents} hydrogen, halogen, cyano or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen,

R ^{4 represents} alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen or Ci-alkoxy,

or together with R ^{3 represents} alkanediyl having 2 to 8 carbon atoms, and

Z represents one of the groupings below

wherein

R ^{5 represents} hydrogen or in each case optionally by fluorine, chlorine, bromine,

Cyano, -CC alkoxy, C ₁ -C alkyl carbonyi or CrC alkoxy carbonyl substituted alkyl, alkenyl, alkynyl, alkylcarbonyl or

Alkoxycarbonyl each having up to 6 carbon atoms, or stands for (in each case only bound to N) arnino or hydroxy.

Particularly preferred compounds of the formula (Ii) are those in which

R ^{1 represents} hydrogen, fluorine or chlorine,

R represents the grouping below,

Wonn

n represents the numbers 0 or 1,

A ^{1 represents} in each case optionally substituted by fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl,

A ¹ furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by fluorine, chlorine, bromine, methyl and / or ethyl,

A ¹ further for each optionally by fluorine, chlorine, bromine, cyano, nitro, carboxy, methyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, dimethylaminosulfonyl, methoxycarbonyl , Propoxycarbonyl or phenyl substituted phenyl, naphthyl, phenylmethyl or phenylethyl,

A furthermore represents thienyl, pyrazolyl or pyridyl, each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyL L ethylsulfonyl, methoxycarbonyl or ethoxycarbonyl,

A, 2 represents methylene or dimethylene, and A for formyl or for acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy which is optionally substituted by fluorine, chlorine, bromine, cyano, methyl or ethyl-substituted cyclopropylcarbonyl, cyclobutylcarbonyl, Cyclcopentylcarbonyl, cyclohexylcarbonyl, Cyclopropylmethylcarbonyl, cyclobutylmethyl carbonyl, Cyclopentylmethylcarbonyl cyclohexylmethylcarbonyl, cyclopropylsulfonyl, Cyclobutylsulfonyl, cyclopentylsulfonyl, cyclo hexylsulfonyl, Cyclopropylmethylsulfonyl, Cyclobutylmethylsulfonyl, Cyclopentylmethylsulfonyl or in each case Cyclohexylsulfonyl, or for phenylcarbonyl, phenylmethylcarbonyl, phenoxycarbonyl, phenylsulfonyl, naphthylsulfonyl, phenylmethylsulfonyl, thienylsulfonyl or pyridinylsulfonyl (which are each optionally substituted by fluorine, chlorine,

Bromine, cyano, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl) is substituted,

R for hydrogen, fluorine, chlorine, bromine, or for each optionally by

^• fluorine and / or chlorine-substituted methyl, ethyl, n- or is i-propyl,

R ⁴ represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and / or chlorine,

or together with R ^{3 represents} trimethylene or tetramethylene, and

represents one of the groupings below

wherein

R ^{5 represents} hydrogen, amino or methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propynyl, butynyl, acetyl, propionyl, each optionally substituted by fluorine, chlorine or cyano, Is methoxycarbonyl or ethoxycarbonyl, or stands for (in each case only bound to N) amino or hydroxy.

A very particularly preferred group of compounds of the formula (Ii) are the VVeerrbbiinndduunnggeenn ddeerr FFoorrmmeell ((IIiiAA)) ,, iinn wweellcchheerr RR ¹¹ ,, RR ²² ,, FR ³ , R ⁴ and R ⁵ which have the meanings given above as being particularly preferred ,

The compounds of formula (Iii) and their preparation are described in WO 96/35679; reference is hereby expressly made to this document.

Preferred compounds of formula (Iii) are those in which

Q represents oxygen or sulfur,

R ^{1 represents} hydrogen, cyano, fluorine or chlorine,

R ^{2 represents} cyano, thiocarbamoyl, fluorine, chlorine, bromine, or alkyl having 1 to 4 carbon atoms optionally substituted by fluorine and / or chlorine,

R ^{3 represents} alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, fluorine, chlorine, bromine, -C ₄ -alkoxy or --C -alkylthio, R furthermore represents cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by cyano, fluorine, chlorine, bromine or Ci-C - alkyl,

R furthermore represents phenyl, naphthyl, benzyl, phenylethyl, thienyl, pyrazolyl,

Pyridinyl or quinolinyl is available, the substituents in each case being suitable: fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, C 1 -C ₄ alkyl, C 1 -C ₄ alkoxy, C 1 -C ₄ alkylthio, dimethylaminosulfonyl , Diethylaminosulfonyl, each optionally substituted by fluorine and / or chlorine -C

₄ -Alkylsulfinyl or -CC ₄ alkylsulfonyl, each optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy substituted Ci-C ₄ - alkoxycarbonyl or in each case optionally by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy substituted phenyl, phenyloxy or phenylthio;

R ^{4 represents} cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by cyano, fluorine, chlorine, bromine or C ₁ -C ₄ alkyl,

R ⁴ furthermore represents optionally substituted phenyl, naphthyl, furyl,

Thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl, pyrimidinyl or quinolinyl is available, the substituents in each case being suitable: fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulfonyl, diethylaminosulfonyl, in each case optionally by and / or chlorine-substituted CrC ₄ -alkyl, -C-C ₄ -alkoxy, C ₁ -C -alkylthio, Cr -alkylsulfmyl or C ₁ -C ₄ -alkylsulfonyl or optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy C ₁ -C ₄ alkoxycarbonyl; R ^{5 represents} hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms,

R ^{6 represents} optionally substituted by fluorine and / or Clilor alkyl having 1 to 4 carbon atoms and

R ^{7 represents} hydrogen, hydroxyl, amino or alkyl, alkoxy, alkenyl or alkynyl, each optionally substituted by fluorine, chlorine or C ₁ -C ₄ -alkoxy, each having up to 6 carbon atoms. ,

Particularly preferred compounds of the formula (Iii) are those in which

Q stands for nitrogen or sulfur,

R ^{1 represents} hydrogen, cyano, fluorine or chlorine,

R represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or trifluoromethyl,

R ³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ³ furthermore for cyclopropyl, cyclobutyl, cyclopentyl or optionally substituted in each case by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl

Cyclohexyl stands,

R ³ furthermore represents optionally substituted phenyl, naphthyl, benzyl,

Phenylethyl, thienyl, pyrazolyl, pyridinyl or quinolinyl, the following being suitable as substituents: fluorine, chlorine, bromine, cyano, nitro, carboxy,

Carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylaminosulfonyl, dim Diethylaminosulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,

R ^{4 represents} cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,

R ⁴ furthermore represents in each case optionally substituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl or pyrimidinyl, where the following may be used as substituents: fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl , Dimethylamino, Dimemylaminosulfonyl or Diethylaminosulfonyl, each optionally by

Fluorine and / or chlorine substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, each optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, in each case optionally by fluorine, chlorine, bromine, cyano, methyl, Methoxy, trifluoromethyl and / or trifluoromethoxy substituted phenyl, phenyloxy or phenylthio,

R ^{5 represents} hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine,

R ^{6 represents} methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine and R ^{7 represents} hydrogen, amino or methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n, each optionally substituted by fluorine and / or chlorine -, i- or s-butoxy, propenyl, butenyl, propynyl or butynyl.

The compounds of the formula (IIIi) and their preparation are described in WO 00/02867; reference is hereby expressly made to this document.

Preferred and particularly preferred compounds of the formula (IIIi) result from the following substituent definitions:

A preferably represents in each case optionally substituted by halogen substituted alkanediyl (alkylene) with 1 to 6 carbon atoms or cycloalkanediyl with 3 to 6 carbon atoms or - in the event that n stands for 1 - also for a single bond or is with Ar via an alkanediyl Grouping linked to 1 to 3 carbon atoms;

Ar preferably represents optionally substituted aryl or arylalkyl, each with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for optionally substituted heterocyclyl or heterocyclylalkyl, each with 1 to 5 carbon atoms and at least one heteroatom (bis to 4 nitrogen atoms and / or optionally 1 or 2 oxygen or sulfur atoms),

where the respective possible substituents can preferably be found in the following list:

Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, Cι-C4-haloalkyl, C -C4-alkoxy, Cι-C4-haloalkoxy, C] _- C4-alkylthio, Cι -C4- Halogenallcylthio, -C-C4-alkylsulfinyl, C; [- C4-haloalkyl-sulfmyl, C ₁ -C ₄ -alkylsulfonyl, Cι-C4-Halόgenalkylsulfonyl, C ^ -alkylamino, di- (Cι-C4-alkyl) -amino , -C-C4-alkyl-carbonyl, -C-C4-alkoxy carbonyl, C \ -C4-alkylamino-carbonyl, di- (C \ -C4-alkyl) -amino-carbonyl ₅ di- (C 1 -C4-alkyl) -aminosulfonyl,

Q preferably represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (C 1 -C ₄ -alkyl),

R ¹ preferably represents hydrogen, amino or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, carboxy, halogen, C1-C4-alkoxy or -C-C4-alkoxy-carbonyl,

R ² preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C1-C4alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,

R ³ preferably represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 6 carbon atoms,

R ⁴ preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine or chlorine,

R ⁵ preferably represents cyano, carbamoyl, thiocarbamoyl, halogen, or alkyl or alkoxy, each optionally substituted by halogen, each having 1 to 4 carbon atoms, and

R ⁶ preferably represents hydrogen, in each case alkyl, alkylcarbonyl or alkoxycarbonyl optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, represents alkylsulfonyl optionally having halogen substituted by 1 to 6 carbon atoms, for each optionally substituted by halogen

Alkenyl, alkenylcarbonyl, alkenylsulfonyl or alkynyl each with up to 6 Carbon atoms, for each cycloalkylcarbonyl or cycloalkylsulfonyl optionally substituted by halogen, each having 3 to 6 carbon atoms in the cycloalkyl groups, for each optionally by nitro, cyano, halogen, C1-C4-alkyl, Cj-G -haloalkyl, C1-C4-alkoxy, C1 -C4- haloalkoxy, -C-C4-alkylthio, -C-C4-haloalkylfhio, Cι-C4-al yl-sulfinyl, Cι-C4-haloalkylsulfmyl, Cι-C4-alkylsulfonyl, Cι-C4-haloalkylsulfonyl, Cι-C4- Alkyl carbonyl, C 1 -C 4 alkoxy carbonyl or di (C 1 -C 4 alkyl amino) sulfonyl substituted arylcarbonyl, arylsulfonyl, arylalkylcarbonyl or arylalkylsulfonyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in

Alkyl part, or for each optionally nitro, cyano, halogen, C1-C4-alkyl, -C-C4-haloalkyl, C1-C4-alkoxy, Cj-C4-haloalkoxy, C1-C4- alkylthio, C] ^ C4-haloalkylfhio, Cι -C4-Alkylsιdfinyl, Cι-C4-haloalkylsulfmyl, Cι-C4-alkylsulfonyl, Cι-C4-haloalkylsulfonyl, C1-C4- alkylcarbonyl, Cι-C4-alkoxy-carbonyl or Oi- (Cι-C4-alkyl-amino ) -sulfonyl-substituted heterocyclylcarbonyl or heterocyclylsulfonyl having 1 to 5 carbon atoms and 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms;

A particularly preferably represents in each case optionally by fluorine and / or

Chlorine-substituted methylene, ethane-l, l-diyl (ethylidene), ethane-l, 2-diyl (dimethyl), propane-l, l-diyl (propylidene), propane-l, 2-diyl or propane-1 , 3-diyl (trimethylene), cyclopropane-l, l-diyl, cyclopropane-l, 2-diyl, cyclobutane-1,1-diyl, cyclopentane-l, l-diyl or cyclohexane-l, l-diyl, or - if n then stands for 1 - also for a single bond, or is linked to Ar via a 1, 2-efhandiyl (dimethylene) grouping;

Ar particularly preferably represents optionally substituted phenyl,

Naphthyl, benzyl, 1-phenyl-ethyl, 2-phenyl-ethyl, 1-phenyl-propyl, 2-phenyl-propyl or 3-phenyl-propyl, or for each optionally substituted

Heterocyclyl or heterocyclylalkyl from the series oxiranyl, oxiranylmethyl, Oxetanyl, Oxetanylmethyl, Furyl, Furylmethyl, Tetrahydrofuryl, Tetrahydrofylmefhyl, Thienyl, Thienylmethyl, Tetrahydrothienyl, Tetrahydrothienylmethyl, Pyrofluylmethylmethyl, Pyridylmethylmethyl Benzopyranyl, benzopyranylmethyl, dihydrobenzopyranyl, dihydrobenzopyranylmethyl, tetrahydrobenzopyranyl, tetrahydrobenzopyranylmethyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl,

where the respective possible substituents can preferably be found in the following list:

Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-

Butylthio, difluoromethylthio, trifluoromethylthio, methylsulfonyl, ethylsulfinyl, n- or i-propylsulfmyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, nyl, methyl, nyl, nyl, ethyl, nyl, nyl, nyl, nyl, nyl, nyl, nyl, nyl, nyl, nyl, nyl, n-methyl, n-methyl, - or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl , Diethylaminocarbonyl, dimethylaminosulfonyl, diethylaminosulfonyl,

Q particularly preferably represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (methyl),

R ¹ particularly preferably represents hydrogen, amino or in each case methyl or ethyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, R ² particularly preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ³ particularly preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine,

R ⁴ particularly preferably represents hydrogen, fluorine or Clilor,

R ⁵ particularly preferably stands for cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy which is optionally substituted by fluorine and / or chlorine .

R ⁶ particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n- or i-butyroyl, n-, i- or sec-valeroyl, pivaloyl, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl, for methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl, each optionally substituted by fluorine and / or chlorine, for ethenyl optionally substituted by fluorine, chlorine and / or bromine, Propenyl, butenyl, ethenylcarbonyl, propenylcarbonyl, butenylcarbonyl, ethynyl, propynyl or butynyl, for each cyclopropylcarbonyl, cyclopropylmethylcarbonyl, cyclobutylcarbonyl, cyclobutylmethylcarbonyl, cyclopentylcarbonyl, cyclopentylmethylcarbonyl, cyclopentylmethylcarbonyl, cyclopentylmethylcarbonyl Cyclohexylmethylcarbonyl, cyclopropylsulfonyl, cyclopropylmefethylsulfonyl, cyclobutylsulfonyl, cyclobutylmethylsulfonyl, cyclopentylsulfonyl, cyclopentylmethylsulfonyl, cyclohexylsulfonyl or cyclo- hexylmethylsulfonyl, each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i Propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfmyl,

Ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propylamethylcarbonyl sulfonyl substituted benzoyl, phenylsulfonyl, phenylacetyl, phenylpropionyl,

Benzylsulfonyl or phenylethylsulfonyl, or for each optionally nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, Methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl or carbonyl, carbonyl dimethylaminosulphonyl or di- ethyl-aminosulfonyl substituted heterocyclylcarbonyl or heterocyclyl sulfonyl from the series furylcarbonyl, furylsulfonyl, thienylcarbonyl, thienylsulfonyl, Pyrazolylcarbonyl, pyrazolylsulphonyl, pyridinylcarbonyl, pyridinylsulfonyl, quinolinylcarbonyl, quinolinylsulfonyl, Pyriminyl- carbonyl, Pyrimidinylsulfonyl ;

A very particularly preferably represents methylene, ethane-l, l-diyl (ethylidene) or ethane-l, 2-diyl (dimethylene),

Ar very particularly preferably represents optionally substituted phenyl, naphthyl or benzyl, the possible substituents in particular can be found in the following list:

Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfonyl, trifluoromethylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonylsulfonyl, trifluoromethyl, nif or propoxycarbonyl,

Q very particularly preferably represents O (oxygen),

R ¹ very particularly preferably represents hydrogen, amino or methyl,

R ² very particularly preferably represents trifluoromethyl,

R ³ very particularly preferably represents hydrogen, chlorine or methyl,

R ⁵ very particularly preferably represents cyano, carbamoyl, thiocarbamoyl, chlorine or bromine,

R ⁶ very particularly preferably represents hydrogen, in each case methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl optionally substituted by fluorine and / or chlorine, or optionally by fluorine and / or or chlorine substituted cyclopropylsulfonyl;

Ar most preferably represents optionally substituted phenyl or naphthyl,

the possible substituents in particular can be found in the following list: Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl, trifluoromethyl, trifluoromethyl, propoxycarbonyl.

The above-mentioned general or preferred definitions for the formulas (Ii), (Iii) and (liii) can be combined with one another, that is, also between the specified preferred ranges.

According to the invention, preference is given to the compounds of the formulas (Ii), (Iii) and (liii) in which there is a combination of the meanings listed above as preferred.

According to the invention, particular preference is given to the compounds of the formulas (Ii), (Iii) and (liii) in which there is a combination of the meanings listed above as being particularly preferred.

Very particularly preferred according to the invention are the compounds of the formulas (Ii), (Iii) and (liii), in which there is a combination of the meanings listed above as being particularly preferred.

Most preferred according to the invention are the compounds of the formulas (Ii), (Iii) and (liii), in which there is a combination of the meanings listed as most preferred above.

In the definitions, the saturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl, are in each case straight-chain or branched. Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.

Insofar as the compounds of the general formulas (Ii), (Iii) and (liii) are chiral, the invention relates to both the enantiomers and any mixtures thereof

Enantiomers, especially the racemates.

The active substances which can be used according to the invention are suitable for systemic and non-systemic control of parasitic pests such as arthropods, preferably insects, arachnids, which are used in animal husbandry and animal breeding in domestic, useful, breeding, zoo, laboratory and experimental applications, with favorable warm-blood toxicity - and hobby animals and occur in their environment. They are effective against all or individual stages of development of the pests and against resistant and normally sensitive types of pests.

The fight against animal pests is intended to prevent diseases and their transmission, deaths and reduced performance (for example in the production of meat, milk, wool, hides, eggs), so that the use of the active compounds enables more economical and simple animal husbandry or is only possible in certain areas.

The preparations according to the invention are preferably used to control ectoparasites.

The above-mentioned ectoparasites include: tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas. These parasites include: From the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .. From the order of the Mallophagida and the subordinates Amblycerina as well Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., Felicola spp ..

From the order Diptera and the subordinates Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp.,

Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp.,

Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp.,

Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp ., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..

From the order of the Siphonapterida e.g. Pulex spp., Ctenocephalides spp.,

Xenopsylla spp., Ceratophyllus spp ..

From the order of the Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..

From the order of the Blattarida e.g. Blatta orientalis, Periplaneta americana,

Blattella germanica, Supella spp ..

From the subclass of Acaria (Acarida) and the orders of the Meta and

Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp.,

Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp.,

Pneumonyssus spp., Sternostoma spp., Varroa spp ..

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) e.g.

Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..

Domestic, farm and breeding animals include mammals such as Cattle, horses,

Sheep, pigs, goats, dog, cat, camels, water buffalo, donkey, rabbit, Fallow deer, reindeer; Fur animals such as B. mink, chinchilla, raccoon; Birds such as chickens, geese, turkeys, ducks and fish such as Cyprinidae, Salmonidae.

Laboratory and experimental animals include mice, rats, rabbits, guinea pigs, golden hamsters, dogs and cats.

Hobby animals include dogs and cats, rabbits, guinea pigs, golden hamsters, horses and ornamental fish.

The application can be prophylactic as well as therapeutic.

The active ingredients are used directly or in the form of suitable preparations enterally, parenterally, dermally, nasally, by treating the environment, also by feed-through preparations or with the aid of shaped articles containing active ingredients, e.g. Strips, plates, ribbons, collars, medallions, ear tags, limb ribbons, marking devices.

The present invention also includes pharmaceutical preparations in dosage units. ^' This means that the formulations are in the form of individual parts, for example tablets, coated tablets, capsules, pills, suppositories and ampoules, the

Active substance content corresponds to a fraction or a multiple of a single dose. The dosage units can e.g. 1,2,3, or 4 or 1/2, 1/3, or 1/4 of a single dose. A single dose preferably contains the amount of active ingredient that is administered in one application.

• The enteral application of the active ingredients takes place, for example, orally in the form of powders, suppositories, tablets, dragées, pills, suspensions, emulsions, capsules, drinkers, granules, drenches, pastes, boluses, medicated feed or drinking water. In the feed through application, a preparation is administered orally to the animal. For example, the major part of the active ingredient is not absorbed and only becomes effective in the animal's excretions after it has passed through the animal. As Preparations may be mentioned here by way of example of controlled release systems such as, for example, microcapsules and slowly eroding shaped bodies.

Tablets, coated tablets, pills, capsules, boluses and granules can contain the active ingredient or the active ingredients or combinations with other active ingredients in addition to the usual ones

Contain carriers, such as a) fillers and extenders, e.g. Starches, milk sugar, cane sugar, glucose, mannitol and silica, b) binders, e.g. Carboxymethyl cellulose, alginates, gelatin, polyvinylpyrrolidone, c) humectants, e.g. Glycerin, d) disintegrants, e.g. Agar-agar, calcium carbonate and sodium carbonate, e) • solution retarders, e.g. Paraffin and f) absorption accelerators, e.g. quaternary ammonium compounds, g) wetting agents, e.g. Cetyl alcohol, glycerol monostearate, h) adsorbents, e.g. Kaolin and bentonite and i) lubricants, e.g. Class talc, calcium and magnesium stearate and solid polyethylene glycols or mixtures of the substances mentioned under a) - i).

The tablets, dragées, pills, capsules, boluses and granules can be provided with the usual coatings and casings, optionally containing opacifying agents, and can also be composed such that they release the active ingredient (s) only or preferably in a certain part of the intestinal tract, possibly with a delay , where as embedding compounds, eg Polymer substances and

Waxes can be used.

The active ingredient (s) can optionally also be in microencapsulated form with one or more of the above-mentioned carriers.

Medicated feed is obtained by mixing, adding premixes in and on feed mixtures or feed pellets. Premixes contain the active ingredient (s) diluted with extenders, such as rock flour, starches, celluloses, proteins and mixtures, binders, such as cellulose and derivatives, vegetable and animal fats and oils. In addition to the active ingredient or ingredients, suppositories can contain the usual water-soluble or water-insoluble excipients, for example polyethylene glycols, fats, for example cocoa fat and higher esters (for example C 14 alcohols with C 16 fatty acids) or mixtures of these substances.

Powders and sprays can contain the usual excipients in addition to the active ingredient (s), e.g. Milk sugar, silicates (calcium, magnesium and / or aluminum e.g. talcum), silica, aluminum hydroxide, calcium carbonates, starches and their derivatives, celluloses and their derivatives and polymaid powder or mixtures of these substances. Sprays can additionally include solvents, emulsifiers, wetting agents, which are mentioned below by way of example, and common propellants, e.g. Chlorinated hydrocarbons, short-chain aliphates e.g. Contain propane, butane and their mixtures.

In addition to the active ingredient (s), ointments, pastes, creams and gels can contain the usual carriers e.g. animal and vegetable fats, waxes, paraffins, starch and their derivatives, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide, acrylates or mixtures of these substances.

In addition to the active ingredient (s), solutions and emulsions can contain the usual carriers such as solvents, solubilizers and emulsifiers.

Examples are given below.

Parenteral use happens e.g. in the form of injection (intramuscular, subcutaneous, intravenous, intraperitoneal) by solutions, emulsions, suspensions or by shaped bodies such as e.g. Implants, e.g. B. consist of biodegradable Polmeren.

For parenteral administration, the solutions and emulsions can also be in sterile and blood isotonic form. Suitable preparations for transdermal application are known to be active ingredient-containing solutions, which may contain substances that require resorption. Resorption-promoting substances are, for example, DMSO (dimethyl sulfoxide), DMF (dimethylformamide), triglycerides and long-chain aliphatic fatty acids, esters and ethers, essential oils and / or their constituents, pyrrolidones, phospholipids, unsaturated organophosphates, amino acids and their esters or amides, macrocyclic compounds, ketones and diketones, alcohols, amides, substituted dioxanes and dioxolanes, derivatized oxazoles, imidazoles, oxazolidones and imidazolinones.

In addition to the active ingredient (s), suspensions can contain the usual carriers such as liquid diluents, e.g. Water, propylene glycol, suspending agents, e.g. ethoxylated isostearyl alcohols, polyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum hydroxide, bentonite, agar and tragacanth or mixtures of these substances.

The formulation formulations mentioned can also contain colorants, preservatives and odor and taste-improving or acceptance-promoting additives, e.g. Peppermint oil and eucalyptus oil, animal and other vegetable oils and sweeteners, e.g. Saccharin.

Said preparations contain the active ingredient in a concentration of 0.1 to 98% by weight, preferably 0.5 to 95% by weight.

For systemic parasite control on animals, it has generally proven advantageous to administer amounts of approximately 0.5 to 100 mg of active ingredient / kg of body weight in order to achieve good effects.

Dermal application is a suitable method for combating ectoparasites and happens e.g. in the form of bathing, diving (dipping), spraying (spraying), pouring on (pour-on or spot-on), washing, shampooing, watering,

Powdering or using solid preparations. Suitable preparations are:

Solutions or concentrates for administration after dilution, sprays e.g.

Aerosols, powder sprays, pump sprays, spot on, pour on solutions for direct

Application, infusion formulations, gels;

Emulsions and suspensions for dermal use as well as solid or semi-solid

preparations;

Formulations in which the active ingredient is in an ointment base or in an oil in

Water or water in oil emulsion base is processed;

Solutions for use on the skin are dripped on, spread on, rubbed in, sprayed on, sprayed on or applied by dipping (dipping), bathing or washing.

The solutions are made by combining the active ingredient in a suitable

Solvent is dissolved and possibly additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives are added.

The following may be mentioned as solvents: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol,

Phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, ketones such as acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, dimethyl-4-oxy-methylene-l, 3-dioxolane.

The active ingredients can optionally also be dissolved in physiologically compatible vegetable or synthetic oils. The following may be mentioned as solubilizers: solvents which promote the solution of the active ingredient in the main solvent or prevent it from precipitating. Examples are polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.

Preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol.

It may be advantageous to add thickeners when preparing the solutions. Thickeners are: inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as

Cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and metacrylates.

Gels that are applied or spread on the skin are produced by adding enough thickening agent to solutions that have been prepared as described above to produce a clear mass with an ointment-like consistency. The thickeners specified above are used as thickeners.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active ingredient being distributed over the surface of the body.

Pour-on formulations are prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, further auxiliaries such as dyes, antioxidants, light stabilizers and adhesives are added.

Dyes are all dyes approved for use on animals, which can be dissolved or suspended.

Excipients are also spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols. Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylated hydroxytoluene, butylated hydroxyanisole, tocopherol.

Light stabilizers are e.g. Substances from the class of benzophenones or

Novantisol acid.

Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.

Emulsions are either water in oil or oil in water.

They are produced by dissolving the active ingredient either in the hydrophobic or in the hydrophilic phase and homogenizing it with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as dyes, preservatives, antioxidants, light stabilizers, viscosity-increasing substances.

The following may be mentioned as the hydrophobic phase (oils): paraffin oils, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic /

Capric acid bigylceride, triglyceride mixture with vegetable fatty acids of chain length C ₈ ι ₂ or other natural fatty acids, specifically selected Partialglyceridge- mix of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the Cs / Cio-fatty acids.

Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, lauric acid hexyl ester, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C ₁₆ -C ₁₈ , isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohols Chain length C ₁₂ -C ₁₈ , isopropyl stearate, oleic acid oleyl ester, oleic acid decyl ester, ethyl oleate, lactic acid ethyl ester, waxy fatty acid esters such as dibutyl phthalate, diisopropyl adipate, ester mixtures related to the latter, inter alia, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.

Fatty acids such as Oleic acid and its mixtures.

The following can be mentioned as the hydrophilic phase:

Water, alcohols such as e.g. Propylene glycol, glycerin, sorbitol and their mixtures.

The following may be mentioned as emulsifiers: nonionic surfactants, e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate,

Glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; mpholytic surfactants such as di-Na-N-lauryl-β-iminodipropionate or lecithin; anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol merormophosphoric acid ester monoethanolamine salt; cationic surfactants such as cetyltrimethylammonium chloride.

The following may be mentioned as further auxiliaries: substances which increase viscosity and stabilize the emulsion, such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes , colloidal silica or mixtures of the listed substances.

Suspensions are produced by suspending the active ingredient in a carrier liquid, optionally with the addition of other auxiliaries such as wetting agents, dyes, absorption-promoting substances, preservatives, antioxidants, light stabilizers.

All homogeneous solvents and solvent mixtures are mentioned as carrier liquids. The surfactants specified above may be mentioned as wetting agents (dispersants).

Further additives mentioned are those mentioned above.

Semi-solid preparations for demial administration differ from the suspensions and emulsions described above only in their higher viscosity.

To prepare solid preparations, the active ingredient is mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape.

All physiologically compatible solid inert substances may be mentioned as carriers. Inorganic and organic substances serve as such. Inorganic substances are e.g. Table salt, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides, silicas, clays, precipitated or colloidal silicon dioxide, phosphates organic are e.g. Flours of vegetable and animal origin, celluloses, starches and their derivatives.

Excipients are preservatives, antioxidants, dyes, which have already been listed above.

Other suitable auxiliaries are lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite.

Ready-to-use preparations contain the active ingredient in concentrations of 1 ppm - 80 percent by weight, preferably from 0.01 - 65 percent by weight. Preferred amounts of active ingredient are 1 to 50 percent by weight, the amounts in the range 5 to 40 percent by weight being very preferred. Preparations which are diluted before use contain the active ingredient in concentrations of 0.5-90 percent by weight, preferably from 1 to 50 percent by weight. ,

In general, it has been found advantageous to use amounts from about 0.5 to about

100 mg, preferably 1 to 50 mg, of active ingredient per kg of body weight per day to achieve effective results.

Particularly noteworthy is the non-systemic application via moldings and powders. Shaped bodies include Collars, pendants for collars (medallions), ear tags, ribbons for attachment to limbs or body parts, adhesive strips and foils, peel-off foils. Powder forms are mentioned above.

In general, it has proven to be advantageous to release solid formulations according to the invention which release amounts of active ingredient from 10 to about 300 mg, preferably 20 to 200 mg, particularly preferably 25 to 160 mg, per kg of body weight of the animal to be treated over the course of at least three months, to apply to achieve good effectiveness.

Thermoplastic and flexible thermosetting plastics as well as elastomers and thermoplastic elastomers come into question for the production of the shaped bodies. Polyvinyl resins, polyurethanes, polyacrylates, epoxy resins, cellulose, cellulose derivatives, polyamides and polyesters which are sufficiently compatible with the abovementioned active ingredient may be mentioned as such. The polymers must have sufficient strength and flexibility so that they do not crack or become brittle during molding. They must be of sufficient durability to withstand normal wear and tear. In addition, the polymers must allow the active ingredient to migrate sufficiently to the surface of the molding.

The polyvinyl resins include polyvinyl halides such as polyvinyl chloride, polyvinyl chloride-vinyl acetate and polyvinyl fluoride; Polyacrylate and polymethacrylate esters, such as polymethyl acrylate and polymethyl methacrylate; and polyvinylbenzenes such as polystyrene and polyvinyltoluene. Special mention should be made of polyvinyl chloride.

The plasticizers which are usually used to plasticize solid vinyl resins are suitable for the production of the molded articles based on polyvinyl resin. The plasticizer to be used depends on the resin and its compatibility with the plasticizer. Suitable plasticizers are, for example, esters of phosphoric acid, such as esters of phthalic acid, such as dimethyl phthalate and dioctyl phthalate, and esters of adipic acid, such as diisobutyl adipate. Other esters, such as the esters of azelaic acid, maleic acid, ricinoleic acid, myristic acid,

Palmitic acid, oleic acid, sebacic acid, stearic acid and trimellitic acid, as well as complex linear polyesters, polymeric plasticizers and epoxidized soybean oils can be used. The amount of plasticizer is about 10 to 50%, preferably about 20 to 45% by weight of the total composition.

The constituent bodies can also contain further constituents, such as stabilizing agents, lubricants, fillers and coloring materials, without changing the basic properties of the composition. Suitable stabilizing agents are antioxidants and agents which protect the tapes from ultraviolet radiation and undesirable degradation during processing, such as extrusion. Some stabilizers, such as epoxidized soybean oils, also serve as secondary plasticizers. For example, stearates, stearic acid and low molecular weight polyethylenes can be used as lubricants. These ingredients can be used in a concentration up to about 5% by weight of the total composition.

In the production of the vinyl-based molded articles, the various constituents are mixed by known processes and compression-molded by known extrusion or injection molding processes. From a technical point of view, the choice of the processing method for the production of the shaped bodies depends in principle on the rheological properties of the strip material and the shape of the desired strip. The processing methods can be set according to the processing technology or the type of shaping. In process technology, the processes can be subdivided according to the rheological conditions they run through. Thereafter, casting, pressing, injection molding and application are possible for viscous strip materials and injection molding, extrusion (extrusion), calendering, rolling and, if necessary, edging for elastoviscous polymers. Divided according to the type of shaping, the moldings according to the invention can be obtained by casting, dipping, pressing, injection molding, extruding, calendering,

Manufacture embossing, bending, deep drawing etc.

These processing methods are known and require no further explanation. In principle, the explanations given above for polyvinyl resins apply to other polymers.

The polyurethanes used as the carrier material are prepared in a manner known per se by reacting polyisocyanates with higher molecular weight compounds having at least two groups which are reactive toward isocyanates, and optionally low molecular weight chain extenders and / or monofunctional ones

Chain breakers manufactured.

In this context, the following should be noted:

Polyisocyanates containing isocyanurate groups, e.g. in US Pat. No. 3,001,973, in DE Patents 1,022,789, 1,222,067 and 1,027,394 and in DE Patents 1,929,034 and 2,004,048; Polyisocyanates containing urethane groups, e.g. be described in DE-PS 752 261 or in US-PS 3 394 164; polyisocyanates containing acylated urea groups according to DE-PS 1 230 778;

Polyisocyanates containing biuret groups, as described, for example, in DE-PS 1 101 394, in US Pat. Nos. 3 124 605 and 3 201 372, and in GB-PS 889 050; polyisocyanates produced by telomerization reactions, as described, for example, in U.S. Patent 3,654,106; Polyisocyanates containing ester groups, as mentioned, for example, in British Pat. Nos. 965,474 and 1,072,956, in US Pat. No. 3,567,763 and in German Pat. No. 1,231,688; Reaction products of the above-mentioned isocyanates with acetals according to DE-PS 1 072 385 and polyisocyanates containing polymeric fatty acid residues according to US-PS 3 455 883.

It is also possible to use the distillation residues obtained in industrial isocyanate production and containing isocyanate groups, optionally dissolved in one or more of the aforementioned polyisocyanates. It is also possible to use any mixtures of the aforementioned polyisocyanates.

Preferred polyisocyanates are generally the tolylene diisocyanates and the diphenylmethane diisocyanates.

Polyhydroxyl compounds already containing urethane or urea groups as well as optionally modified natural polyols such as castor oil, carbohydrates or starch, polyester amides and polyamides also count e.g. the predominantly linear condensates obtained from polyvalent saturated and unsaturated carboxylic acids or their anhydrides and polyvalent saturated and unsaturated amino alcohols, diamines, polyamines and their mixtures can be used for this purpose.

Addition products of alkylene oxides with phenol-formaldehyde resins or with urea-formaldehyde resins can also be used according to the invention.

Representatives of these connections are e.g. in High Polymers, Vol. XVI, "Polyurethanes, Chemistry and Technology", written by Saunders-Frisch, Interscience Publishers,

New York, London, volume 1, 1962, pages 32 - 42 and pages 44 - 54 and volume II, 1964, pages 5 -6 and 198 - 199, as well as in the plastics manual, volume VII, Vieweg-Höchtlen, Carl-Hanser - Verlag, Munich, 1966, for example on pages 45-71. Mixtures of the abovementioned compounds with at least two hydrogen atoms which are reactive toward isocyanates and have a molecular weight of 400-10,000, for example mixtures of polyethers, can of course be used.

When selecting the higher molecular weight polyol component used for the production of the polyurethane, it should be noted that the finished polyurethane. should not be swellable in water. The use of an excess of polyhydroxy compounds with ethylene oxide units (polyethylene glycol polyether or polyester with diethylene or triethylene glycol as the diol component) should therefore be avoided.

Thermoplastic elastomers are particularly emphasized for the production of the shaped bodies. These are materials that contain elastomeric phases in thermoplastically processable polymers either physically mixed in or chemically bound. A distinction is made between polymer blends in which the elastomeric phases are part of the polymer structure. Due to the structure of the thermoplastic elastomers, hard and soft areas are side by side. The hard areas form a crystalline network structure or a continuous phase whose spaces are filled with elastomeric segments. Because of this structure, these materials have rubber-like properties.

There are 5 main groups of thermoplastic elastomers:

1 copolyester

2 polyether block amides (PEBA) 3 thermoplastic polyurethanes (TPU) 4. Thermoplastic polyolefins (TPO) 5 styrene block copolymers

Suitable copolyesters (segmented polyester elastomers) are, for example, from one

Large number of recurring, short-chain ester units and long-chain ester units, which are united by ester bonds, built up, the short-chain ester units making up about 15-65% by weight of the copolyester and having the formula (II).

in which

R represents a divalent radical of a dicarboxylic acid which has a molecular weight of less than about 350,

D represents a divalent radical of an organic diol that has a molecular weight below about 250.

The long-chain ester units make up about 35-85% by weight of the copolyester and have the formula (in)

in which

R represents a divalent radical of a dicarboxylic acid which has a molecular weight of less than about 350,

G represents a divalent residue of a long chain glycol which has an average molecular weight of about 350 to 6000. Methods for the synthesis of such copolyesters are known from DOS 2239 271, DOS 2 213 128, DOS 2 449 343 and US Pat. No. 3,023,192.

Suitable copolyesters are available, for example, under the trade names ^® Hytrel from Du Pont, ^® Pelpren from Toyobo ^® , Arnitel from Akzo, ^® Ectel from Eastman Kodak and ^® Riteflex from Hoechst.

Suitable polyether block amides are, for example, those which consist of polymer chains which are composed of repeating units corresponding to the formula (IV).

in which

A is the polyamide chain derived from a polyamide with 2 carboxyl end groups by loss of the latter and

B is the polyoxyalkylene glycol with terminal OH groups derived from loss of the latter polyoxyalkylene glycol chain and

n is the number of units forming the polymer chain.

The end groups here are preferably OH groups or residues of compounds which terminate the polymerization.

The dicarboxylic acid polyamides with the terminal carboxyl groups are obtained in a known manner, for example by polycondensation of one or more lactams or / and one or more amino acids, furthermore by polycondensation of one Dicarboxylic acid with a diamine, in each case in the presence of an excess of an organic dicarboxylic acid, preferably with terminal carboxyl groups. These carboxylic acids become part of the polyamide chain during the polycondensation and attach themselves in particular to the end of the chain, whereby an oc-ω-dicarboxylic acid polyamide is obtained. The dicarboxylic acid also acts as a chain terminator, which is why it is also used in excess.

The polyamide can be obtained starting from lactams and / or amino acids with a hydrocarbon chain consisting of 4-14 C atoms, e.g. of caprolactam, oenantholactam, dodecalactam, undekanolactam, decanolactam, 11-amino-undecanoic or 12-aminododecanoic acid.

Examples of polyamides, such as those produced by polycondensation of a dicarboxylic acid with a diamine, are the condensation products of hexamethylenediamine with adipic, azelaic, sebacic and 1, 12-dodecanedioic acid, and the condensation products of nonamethylene diamine and adipic acid.

In the case of the dicarboxylic acids used for the synthesis of the polyamide, that is to say on the one hand for fixing a carboxyl group at each end of the polyamide chain and on the other hand as chain terminators, those having 4-20 C atoms come into play

Question, especially alkanedioic acids, such as succinic, adipic, cork, azelaic, sebacic, undecanedio or dodecanedioic acid, further cycloaliphatic or aromatic dicarboxylic acid, such as terephthalic or isphthalic or cyclohexane-1, 4-dicarboxylic acid.

The polyoxyalkylene glycols containing terminal OH groups are unbranched or branched and have an alkylene radical with at least 2 carbon atoms. In particular, these are polyoxyethylene, polyoxypropylene and polyoxytetramethylene glycol, as well as copolymers thereof. The average molecular weight of these OH group-terminated polyoxyalkylene glycols can be in a wide range, advantageously between 100 and 6000, in particular between 200 and 3000.

The proportion by weight of the polyoxyalkylene glycol, based on the total weight of the polyoxyalkylene glycol and dicarboxylic acid polyamide used to produce the PEBA polymer, is 5-85%, preferably 10-50%.

Methods for the synthesis of such PEBA polymers are known from FR-PS 7 418 913 (No. of the publication 2 273-021), DOS 2 802 989, DOS 2 837 687, ^' DOS 2 523 991,

EP-S 0 095 893, DOS 2 712 987 and DOS 2 716 004 are known.

Those PEBA polymers which, in contrast to those previously described, have a statistical structure are particularly suitable. Suitable and preferably suitable PEBA polymers are, for example, under the trade names ^® PEBAX from Atochem, ^® Vestamid

Hüls AG, ^® Grilamid from EMS-Chemie and ^® Kellaflex from DSM available.

The application can be prophylactic as well as therapeutic.

In the case of collars, the concentration of the active ingredients is preferably 1 to

50%; in the case of medallions, pendants and ear tags preferably 2.5 to 35%, in the case of foils, adhesive strips preferably 0.1 to 15%.

The following forms may be mentioned as examples for the use of the active substances mentioned in the environment of the animals:

Depending on their respective physical and / or chemical properties, the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, sprays such as aerosols or pump sprays, ultra-fine encapsulations in polymeric materials, paints and ULV -Cold and warm mist formulas. These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and the like their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. The following are suitable as solid carriers: for example, natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates. Possible solid carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules made from inorganic and organic flours as well as granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are, for example, lignin sulfite liquor and methyl cellulose. Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phmalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active substances mentioned can be in the liquid, solid preparations as well

Shaped bodies in a mixture with synergists or other active substances (co-active substances), such as. Known fungicides, bactericides, acaricides, nematicides or insecticides can be used, e.g. to broaden the spectrum of effects or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The co-active ingredients preferably include insecticides such as phosphorus-containing compounds, i.e. Phosphoric or phosphonic acid esters, natural or synthetic pyrethroids, carbamates, amidines, juvenile hormones and juvenoid synthetic active ingredients.

The phosphoric or phosphoric acid esters include:

0-ethyl-0- (8-quinolyl) phenyl thiophosphate (Quintiofos), 0.0-diethyl 0- (3-chloro-4-methyl-7-coumarinyl) thiophosphate (Coumaphos),

0.0-the yl-0-phenylglyoxylonitrile oxime thiophosphate (phoxime), 0.0-diethyl-0-cyanochlorobenzaldoxime thiophosphate (chlorophoxime), 0.0-diethyl-0- (4-bromo-2,5-dichlorophenyl) phosphorothionate (bromophos-ethyl), 0,0,0 ', 0 '-Tetraethyl-S, S'-methylene-di (phosphorodithionate) (Ethion), 2,3-p-dioxanedithiol-S, S-bis (0,0-diethylphosphorodithionate, 2-chloro-1 - (2,4- dichlorophenyl) vinyl diethyl phosphate (chlorfenvinphos),

0.0-Dimemyl-0- (3-methyl-4-methylthiophenyl) thionophosphoric acid ester (fenthion).

The carbamates include:

2-isopropoxyphenylmethyl carbamate (propoxur),

1-naphthyl-N-methyl carbamate (carbaryl).

The synthetic pyrefhroids include compounds of the formula I.

Formula I.

in which

1

R and R represent halogen, optionally halogen-substituted alkyl, optionally halogen-substituted phenyl,

R ^{3 represents} hydrogen or CN,

R represents hydrogen or halogen,

R ^{5 represents} hydrogen or halogen,

Synthetic pyrethroids of the formula I in which R ^{1 represents} halogen, in particular fluorine, chlorine, bromine,

R represents halogen, in particular fluorine, chlorine, bromine, trihalomethyl, phenyl, chlorophenyl,

R represents hydrogen or CN,

R ^{4 represents} hydrogen or fluorine,

R ^{5 represents} hydrogen.

Synthetic pyrethroids of the formula I, in which

R ^{1 represents} chlorine,

R ^{2 represents} chlorine, trifluoromethyl, p-chlorophenyl,

^' R ³ stands for CN,

R ^{4 represents} hydrogen or fluorine,

R ^{5 represents} hydrogen.

Compounds of the formula I, in which

R ^{1 represents} chlorine,

R ^{2 represents} chlorine or p-chlorophenyl,

R ^{3 represents} CN, R represents fluorine in the 4-position,

R ^{5 represents} hydrogen.

The following may be mentioned in detail:

3 - [2- (4-chloro-phenyl) -2-chlorovinyl] -2,2-dimethyl-cyclo-propanecarboxylic acid [(oc-cyano-4-fluoro-3-phenoxy) benzyl] ester (flumethrin),

2,2-dimemyl-3- (2,2-dicWorvinyl) -cyclopropanecarboxylic acid-oc-cyano (4-fluoro-3-phenoxy) -benzyl ester (cyfluthrin) and its enantiomers and stereomers,

oc-cyano-3-phenoxybenzyl (+) - cis, 1rans-3- (2,2-dibromvmyl) -2,2-dimethylcyclopropane carboxylate (deltamethrin),

2,2-dimemyl-3- (2,2-dic orvinyl) -cyclopropanecarboxylic acid-3c-cyano-3-phenoxyberιzyl ester (cypermethrin),

3-phenoxybenzyl (+) - cis, trans-3 - (2,2-dichlorovinyl) -2,2-dimethylcyclopropane carboxylate

(Permethrin),

oc- (p-Cl-phenyl) isovaleric acid oc-cyano-3-phenoxy-benzyl ester (Fenvalerate),

2-cyano-3-phenoxybenzyl-2- (2-CMOR-oc, cc, oc-trifluoro-p-toluidino) -3-methylbutyrate

(Fluvalinate).

The amidines include:

3-Memyl-2- [2,4-dimemyl-phenylimino] -thiazoline, 2- (4-chloro-2-methylphenylimino) -3-methylthiazolidine,

2- (4-chloro-2-methylphenylimino) -3 - (isobutyl-1-enyl) thiazolidine

l, 5-bis (2,4-dimethylphenyl) -3-methyl-l, 3,5-triazapenta-l, 4-diene (amitraz).

Juvenile hormones or juvenile hormone-like substances include substituted diaryl ethers, benzoyl ureas and triazine derivatives. Juvenile hormones and juvenile hormone-like substances include in particular compounds of the following formulas:

03

50 -

The substituted diaryl ethers include, in particular, substituted alkoxydiphenyl ethers or diphenylmefanes of the general formula I

in which

R ^{1 represents} hydrogen, halogen, alkyl, alkoxy, alkylthio,. Haloalkyl, haloalkoxy, haloalkylthio, dioxyalkylene, dioxyhalogenalkylene, CN, NO ₂ , alkenyl, alkynyl, alkoxyalkyl, alkoxyalkoxy, hydroxyalkoxy,

R ^{2 represents} the radicals specified for R ¹ ,

R ^{3 represents} the radicals specified for R ¹ ,

R j4 represents hydrogen, alkyl, haloalkyl or halogen,

R ^{5 represents} the radicals indicated for R ⁴ , Het stands for optionally substituted heteroaryl which is not bound to the rest of the group via the heteroatom,

X, Y independently of one another represent -O-, -S-

Z represents -O-, -S-, -CH ₂ -, -CHCH ₃ -, -C (CH ₃ ) ₂ -,

m and n independently of one another represent 0, 1, 2, 3 but their sum is equal to or greater than 2.

Compounds of the formula I are particularly preferred

in which

R ^{1 is} hydrogen, methyl, trifluoromethyl, methoxy, trifluoromethoxy, chlorine, fluorine

R ^{2 represents} hydrogen,

R ^{3 represents} hydrogen, fluorine, chlorine, methyl,

R ^{4 represents} hydrogen or methyl,

R ^{5 represents} methyl, ethyl, trifluoromethyl or hydrogen,

Het is pyridyl or pyridazinyl which are optionally substituted by fluorine, chlorine, methyl, NO ₂ , methoxy, methylmercapto,

X stands for O,

Y stands for O, Z is O, CH ₂ or - (CH ₃ ) ₂ -, m is 1, n is 1.

The following connections are specifically mentioned:

Benzoyl ureas include compounds of the formula (V):

in which

R ^{1 represents} halogen,

R represents hydrogen or halogen,

R represents hydrogen, halogen or C - alkyl,

R ⁴ for halogen, l-5-halogen-C _1-4 -alkyl, Cμ- alkoxy, l-5-halogen-C _1- -alkoxy,

C _M -alkylthio, 1-5-halo-C _1- -alkylthio, phenoxy or pyridyloxy which may optionally be substituted by halogen, C _1-4 -alkyl, 1-5- Halogen-C _1-4 -alkyl, C ^ -alkoxy, 1-5-halogen-Cm-alkoxy, C _1-4 -alkylthio, 1-5-halogen-C i -C ₄ -aikylthio.

In particular, the following should be mentioned:

In addition, the following examples of other insecticides and acaricides and nematicides which can be used as co-active substances are mentioned:

Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin,

Azamethiphos, Azinphos A, Azinphos M, Azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis,

Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb,

Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Biopermethrin, Bistrifluron, BPMC, Bromophos A, Bufencarb, Buprofezin,

Butathiofos, Butocarboxim, Butylpyridaben,.

Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap,

Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron,

Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Chromafenozide, Cis- Resmethrin, Cispermethrin, Clocythrm, Cloethocarb, Clofentezine, Clothianidine,

Cyanophos, cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,

Cypermethrin, cyromazine,

Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon,

Dichlorvos, Dicofol, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Dpcusat-sodium, Dofenapyn,

Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp.,

Eprinomectin, Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox,

Etoxazole, Etrimfos,

Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropafhrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate,

Fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,

Flufenoxuron, Flumethrin, Flutenzine, Fluvalinate, Fonophos, Fosmefhilan,

Fosthiazate, Fubfenprox, Furafhiocarb,

Granuloseviruses Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,

Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin, Kempolyederviren

Lambda cyhalothrin, lufenuron

Malathion, mecarbam, metaldehyde, methamidophos, metharhilic anisopliae,

Metharhilicium flavoviride, methidathione, methiocarb, methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin,

Milbemycin, monocrotophos,

Naled, Nitenpyram, Nithiazine, Novaluron

Omethoate, Oxamyl, Oxydemethon M

Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb Pirimiphos A,

Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothoat,

Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion,

Pyrimidifen, pyriproxyfen,

Quinalphos, Ribavirin

Salithion, Sebufos, Selamectin, Silafluofen, Spinosad, Spirodiclofen, Sulfotep,

sulprofos,

Tau fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron,

Tefluthrin, Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Tetradifon Thetacypermethrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringinhrine, Tral

Triarathenes, triazamates, triazophos, triazuron, trichlophenidines, trichlorfon,

Triflumuron, trimethacarb,

Namidothion, 'Naniliprole, Nerticillium lecanii

YI 5302

Zeta-cypermethrin, zolaprofos

(1 R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) -furanylidene) - methyl] -2,2-dimethylcyclopropane carboxylate (3 - Phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropane decarboxylate l - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-l, 3,5-triazin-2 (1H) - imine

2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole

2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione 2-chloro-N - [[[4- (l-phenylethoxy) phenyl] amino] carbonyl] benzamide

2-Chloro-N - [[[4- (2,2-dichloro-l, 1-difluoroethoxy) phenyl] amino] carbonylj-benzamide

3-methylphenyl propyl carbamate

4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene

4-Chloro-2- (l, l-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone

4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone

4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlθφhenyl) -3 (2H) -pyridazinone

Bacillus thuringiensis strain EG-2348 benzoic acid [2-benzoyl-1 - (1, 1-dimethylethyl) hydrazide

Butanoic acid 2,2-dimethyl-3- (2,4-dichloro phhenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4-yl ester

[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] cyanamide

Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde ethyl- [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy ] ethyl] carbamate

N- (3,4,4-trifluoro-1-oxo-3-butenyl) glycine

N- (4-Chloφhenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-lH-pyrazol-

1-carboxamide

N- [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine N-methyl-N '- (l-methyl-2-propenyl) -l, 2-hydrazinedicarbothioamide

N-methyl-N'-2-propenyl-1, 2-hydrazinedicarbothioamide

O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat

N-cyanomethyl-4-trifluoromethyl-nicotinamide

3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propoxyj-benzene A mixture with other known active ingredients, such as growth regulators, is also possible.

Co-active ingredient and synergist concentrations can be varied widely from 0.1 to 25% by weight, preferably from 1 to 10% by weight.

The active ingredients listed below are used in the following examples:

example 1

Blowfly larva test / development-inhibiting effect

Test animals: Lucilia cuprina larvae Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in one ml of dimethyl sulfoxide. To produce a suitable formulation, the active ingredient solution is diluted with water to the desired concentration.

About 20 Lucilia cuprina larvae are placed in a test tube containing approx. 1 cm ³ horse meat and 0.5 ml of the active ingredient preparation to be tested. After 48 hours, the effectiveness of the active ingredient preparation is determined as% larval mortality.

The test tubes are then transferred to beakers with a bottom covered with sand. After a further 12 days, the test tubes are removed and the dolls and flies are counted. The development inhibitory effect is given by the inhibition of hatching after 1.5 times the development time of an untreated control in% (ratio of pupae to hatched flies).

Test results:

Example 2

Test with cat fleas / development inhibitory effect

Test animals: All stages (eggs, larvae, pupae and adults) of

Ctenocephalides felis solvent: dimethyl sulfoxide (DMSO)

To produce a suitable formulation, a suitable active ingredient solution is prepared from 20 mg of active ingredient with 1 ml of DMSO. The solution thus obtained is diluted with water to the desired concentration.

200 μl of this active ingredient preparation are added to 1.8 g of rearing medium (blood meal medium: 125 parts sea sand, 20 parts rat feed, 3 parts blood meal, 2 parts dry yeast) in disposable 2.0 cm ³ tubes, mixed homogeneously and dried overnight. A spatula tip of sieved flea eggs (from artificially infected cats) is placed on top.

The effectiveness of the active substance preparation is determined every 2 days up to 1 times the development time of the control batch by examining the batches for development stages of the fleas.

The criterion for the in vitro effect of a substance is the inhibition of flea development or a development standstill before the adult stage. 100% means that no adult fleas developed; 0% means that adult fleas have hatched.

Test results:

Claims

Patentansprtiche

1. Connections

(i) of the formula (Ii)

in which

R ^{1 represents} hydrogen or halogen,

R> 2 represents the grouping below,

, SO, -A '

N

(A ² ) _n -A ³

worm

n represents the numbers 0 or 1,

A ^{1 represents} an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl arylalkyl, heterocyclyl or heterocyclylalkyl,

A ^{2 represents} alkanediyl (alkylene), and A for formyl or for an optionally substituted alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, cycloalkylcarbonyl,. Cycloalkylalkylcarbonyl, cycloalkylsulfonyl, cycloallcylalkylsulfonyl, arylcarbonyl, arylalkylcarbonyl, aryloxycarbonyl, arylsulfonyl, heterocyclylsulfonyl or heterocyclylalkylsulfonyl,

R represents hydrogen, halogen, cyano or optionally substituted alkyl,

R represents optionally substituted alkyl or

together with R> 3 represents alkanediyl,

represents one of the groupings below

wherein

R represents hydrogen or optionally substituted alkyl, alkenyl, alkynyl, alkylcarbonyl or alkoxycarbonyl, or represents amino or hydroxy (in each case only bonded to N),

or (ii) of the formula (Iii)

in which

Q represents oxygen or sulfur,

R ^{1 represents} hydrogen, cyano or halogen,

R represents cyano, thiocarbamoyl, halogen or optionally substituted alkyl,

R represents optionally substituted alkyl, cycloalkyl, aryl,

Arylalkyl or heteroaryl,

R ⁴ for each optionally substituted cycloalkyl, aryl or

Heteroaryl stands,

R represents hydrogen, halogen or optionally substituted alkyl or alkoxy,

R represents optionally substituted alkyl and R ^{7 represents} hydrogen, hydroxyl, amino or optionally substituted alkyl, alkoxy, alkenyl or alkynyl,

or

(iii) of the formula (liii)

in which

n represents the numbers 0 or 1,

A stands for optionally substituted alkanediyl (alkylene) or cycloalkanediyl, or - with the proviso that n stands for 1 - also stands for a single bond or is linked to Ar via an alkanediyl group,

Ar represents optionally substituted aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (alkyl),

R ^{1 represents} hydrogen, amino or optionally substituted

Alkyl stands, R ^{2 stands} for carboxy, cyano, carbamoyl, thiocarbamoyl or for optionally substituted alkyl or alkoxycarbonyl,

R ^{3 represents} hydrogen, halogen or optionally substituted alkyl,

R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,

R ^{5 stands} for cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl or alkoxy, and

R ⁶ for hydrogen or for each optionally substituted

Alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkynyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, arylalkylcarbonyl, arylalkylsulfonyl, heterocyclylcarbonyl or heterocyclylsulfonyl

to fight parasites on animals and in their environment.

Agents containing compounds of the formulas (Ii), (Iii) and / or (Iiii) and pharmaceutically acceptable carriers and / or auxiliaries.

Use of compounds of the formulas (Ii), (Iii) and / or (liii) for controlling parasites on animals and / or in their surroundings.

Use according to claim 3 for combating ectoparasites. Use of compounds of the formulas (Ii), (Iii) and / or (liii) according to Claim 1 for the preparation of agents for controlling parasites on animals and / or in their surroundings.

A method for controlling parasites on animals and / or in their environment, in which an effective amount of a compound of the formulas (Ii), (Iii) and / or (liii) according to Claim 1 is applied to the animals.