DE10211414A1 - New use of N-(4-cyanophenyl)-diaza-heterocycles or N-substituted aminophenyl-uracils, for systemic or non-systemic control of parasites on animals or in their surroundings - Google Patents

Abstract

The use of N-(4-cyanophenyl)-diaza-heterocycles (I), N-sulfonylated aminophenyl-uracils (II) or N-acylated aminophenyl-uracils (III) for controlling parasites on animals and in their surroundings, is new. The use of N-(4-cyanophenyl)-diaza-heterocycles of formula (I), N-sulfonylated aminophenyl-uracils of formula (II) or N-acylated aminophenyl-uracils of formula (III) for controlling parasites on animals and in their surroundings, is new: R1 = H or halo; R2 = -N(SO2A1)-(A2)n-A3; n = 0 or 1; A1 = alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl (all optionally substituted (os)); A2 = alkylene; A3 = CHO; or alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl, arylcarbonyl, aralkylcarbonyl, aralkoxycarbonyl, arylsulfonyl, heterocyclylsulfonyl or heterocyclylalkylsulfonyl (all os); R3 = H, halo, CN or os alkyl; R4 = os alkyl; or R3+R4 = os alkyl; D = -N(R5)-CO- or -N=C(OR5)-; R5 = H; alkyl, alkenyl, alkynyl, alkylcarbonyl or alkoxycarbonyl (all os); or (only if bonded to N) OH or NH2; Q = O or S; S1 = H, CN or halo; S2 = CN, CSNH2, halo or os alkyl; S3 = alkyl, cycloalkyl, aryl, aralkyl or heteroaryl (all os); S4 = cycloalkyl, aryl or heteroaryl (all os); S5 = H, halo, os alkyl or os alkoxy; S6 = os aryl; S7 = H, OH or NH2 or alkyl, alkoxy, alkenyl or alkynyl (all os); A = os alkylene or os cycloalkylene; or if n = 1 may also be a direct bond or be linked to Ar via an alkylene group; Ar = aryl, aralkyl, heterocyclyl or heterocyclylalkyl (all os); Q' = O, S, SO, SO2, NH or N(alkyl); T1 = H, NH2 or os alkyl; T2 = COOH, CN, CONH2, CSNH2, os alkyl or os alkoxycarbonyl; T3 = H, halo or os alkyl; T4 = H, CN, CONH2, CSNH2 or halo; T5 = CN, CONH2, CSNH2, halo, os alkyl or os alkoxy; and T6 = H; or alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkynyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, aralkylcarbonyl, aralkylsulfonyl, heterocyclylcarbonyl or heterocyclylsulfonyl (all os). Independent claims are also included for: (1) compositions comprising (I), (II) and/or (III) plus pharmaceutical carriers and/or auxiliaries; and (2) a method for controlling parasites on animals and in their surroundings, comprising application of (I), (II) and/or (III).

Description

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 property described (cf. WO 91/00278, DE 42 37 920, EP 408 382 / US 5 084 084, EP 438 209, EP 473 551). In WO 95/29168 there are herbicidal N-cyanoaryl nitrogen heterocycles described, which also have insecticidal activity. The fight against parasites However, animals or in their surroundings are not suggested.

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 are herbicides and have 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). This However, compounds have so far not been mentioned as herbicides or as insecticides Gained meaning. There is also no reference to the use of these compounds to combat parasites on animals or in their environment.

Surprisingly, it was found that 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 surroundings.

• a) der Formel (Ii)
  
  
  in welcher
  R¹ für Wasserstoff oder Halogen steht,
  R² für die nachstehende Gruppierung steht,
  
  
  worin
  n für die Zahlen 0 oder 1 steht,
  A¹ für jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Aryl Arylalkyl, Heterocyclyl oder Heterocyclylalkyl steht,
  A² für Alkandiyl (Alkylen) steht, und
  A³ für Formyl oder für einen jeweils gegebenenfalls substituiertes Alkylcarbonyl, Alkoxycarbonyl, Alkylsulfonyl, Cycloalkylcarbonyl, Cycloalkylalkylcarbonyl, Cycloalkylsulfonyl, Cycloalkylalkylsulfonyl, Arylcarbonyl, Arylalkylcarbonyl, Aryloxycarbonyl, Arylsulfonyl, Heterocyclylsulfonyl oder Heterocyclylalkylsulfonyl steht,
  R³ für Wasserstoff, Halogen, Cyano oder für gegebenenfalls substituiertes Alkyl steht,
  R⁴ für gegebenenfalls substituiertes Alkyl steht oder
  zusammen mit R³ für Alkandiyl steht,
  Z für eine der nachstehenden Gruppierungen steht
  
  
  worin
  R⁵ für Wasserstoff oder jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Alkylcarbonyl oder Alkoxycarbonyl steht, oder für (jeweils nur an N gebundenes) Amino oder Hydroxy steht,

oder

• a) der Formel (Iii)
  
  
  in welcher
  Q für Sauerstoff oder Schwefel steht,
  R¹ für Wasserstoff, Cyano oder Halogen steht,
  R² für Cyano, Thiocarbamoyl, Halogen oder für gegebenenfalls substituiertes Alkyl steht,
  R³ für jeweils gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aryl, Arylalkyl oder Heteroaryl steht,
  R⁴ für jeweils gegebenenfalls substituiertes Cycloalkyl, Aryl oder Heteroaryl steht,
  R⁵ für Wasserstoff, Halogen oder für jeweils gegebenenfalls substituiertes Alkyl oder Alkoxy steht,
  R⁶ für gegebenenfalls substituiertes Alkyl steht und
  R⁷ für Wasserstoff, Hydroxy, Amino oder für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl oder Alkinyl steht,

oder

• a) der Formel (Iiii)
  
  
  in welcher
  n für die Zahlen 0 oder 1 steht,
  A für jeweils gegebenenfalls substituiertes Alkandiyl (Alkylen) oder Cycloalkandiyl steht, oder - mit der Maßgabe, dass dann n für 1 steht - auch für eine Einfachbindung steht oder mit Ar über eine Alkandiyl- Gruppierung verknüpft ist,
  Ar für jeweils gegebenenfalls substituiertes Aryl, Arylalkyl, Heterocyclyl oder Heterocyclylalkyl steht,
  Q für O(Sauerstoff), S(Schwefel), SO, SO₂, NH oder N(Alkyl) steht,
  R¹ für Wasserstoff, Amino oder gegebenenfalls substituiertes Alkyl steht,
  R² für Carboxy, Cyano, Carbamoyl, Thiocarbamoyl oder für jeweils gegebenenfalls substituiertes Alkyl oder Alkoxycarbonyl steht,
  R³ für Wasserstoff, Halogen oder gegebenenfalls substituiertes Alkyl steht,
  R⁴ für Wasserstoff, Cyano, Carbamoyl, Thiocarbamoyl oder Halogen steht,
  R⁵ für Cyano, Carbamoyl, Thiocarbamoyl, Halogen, oder für jeweils gegebenenfalls substituiertes Alkyl oder Alkoxy steht, und
  R⁶ für Wasserstoff oder für jeweils gegebenenfalls substituiertes Alkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkylsulfonyl, Alkenyl, Alkenylcarbonyl, Alkenylsulfonyl, Alkinyl, Cycloalkylcarbonyl, Cycloalkylsulfonyl, Arylcarbonyl, Arylsulfonyl, Arylalkylcarbonyl, Arylalkylsulfonyl, Heterocyclylcarbonyl oder Heterocyclylsulfonyl steht,

zur Bekämpfung von Parasiten an Tieren und in deren Umgebung. The invention relates to connections

• a) of the formula (Ii)
  
  
  in which
  R ^{1 represents} hydrogen or halogen,
  R ^{2 represents} the grouping below,
  
  
  wherein
  n represents the numbers 0 or 1,
  A ^{1 represents} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl arylalkyl, heterocyclyl or heterocyclylalkyl,
  A ^{2 represents} alkanediyl (alkylene), and
  A ^{3 represents} formyl or an optionally substituted alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl, arylcarbonyl, arylalkylcarbonyl, aryloxycarbonyl, arylsulfonyl, heterocyclylsulfonyl or heterocyclyl
  R ^{3 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
  
  
  wherein
  R ^{5 represents} hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, alkylcarbonyl or alkoxycarbonyl, or represents amino or hydroxy (in each case only bonded to N),

or

• a) 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 ^{4 represents} in each case optionally substituted cycloalkyl, aryl or heteroaryl,
  R ^{5 represents} hydrogen, halogen or optionally substituted alkyl or alkoxy,
  R ^{6 represents} optionally substituted alkyl and
  R ^{7 represents} hydrogen, hydroxyl, amino or optionally substituted alkyl, alkoxy, alkenyl or alkynyl,

or

• a) 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 represents} cyano, carbamoyl, thiocarbamoyl, halogen, or in each case optionally substituted alkyl or alkoxy, and
  R ^{6 stands} for hydrogen or for optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkynyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, arylalkylcarbonyl, arylalkylsulfonyl, heterocycylcyclyllylcarbonyl

to fight parasites on animals and in their environment.

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

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 ^{1 represents} hydrogen, fluorine, chlorine or bromine,
R ^{2 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 which is in each case optionally substituted by halogen, cyano or C ₁ -C ₄ -alkyl and has 3 to 8 carbon atoms in the cycloalkyl part and optionally 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 alkylsulfinyl or C ₁ -C ₄ 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) substituted 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 further 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 alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ alkoxycarbonyl (which are each optionally substituted by halogen), by phenyl, phenoxy or phenylthio (which are each optionally by halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and / or C ₁ -C 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,
A ^{2 represents} alkanediyl having 1 to 4 carbon atoms, and
A ³ 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, cycloalkylalkylcarbonyl optionally substituted by halogen, cyano or C ₁ -C ₄ alkyl , 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, naphthylylylonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonsyl each optionally substituted by halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy or C ₁ -C ₄ alkoxycarbonyl substituted) stands,
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 with 1 to 6 carbon atoms optionally substituted by halogen or C ₁ -C ₄ 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 substituted by fluorine, chlorine, bromine, cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl alkyl, alkenyl, alkynyl, alkylcarbonyl or Alkoxycarbonyl each having up to 6 carbon atoms, or stands for (in each case only bound to N) amino or hydroxy.

Particularly preferred compounds of the formula (Ii) are those in which
R ^{1 represents} hydrogen, fluorine or chlorine,
R ^{2 represents} the grouping below,


wherein
n represents the numbers 0 or 1,
A ¹ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, each optionally substituted by fluorine or chlorine,
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, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, dimethylaminosulfonyl, methoxycarbonyloxy, methoxycarbonyl, carbonyl or phenyl substituted phenyl, naphthyl, phenylmethyl or phenylethyl,
A ¹ furthermore represents thienyl, pyrazolyl or pyridyl, each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl or ethoxycarbonyl,
A ^{2 represents} methylene or dimethylene, and
A ³ 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, represents optionally in each case fluorine, chlorine, bromine, cyano, methyl or ethyl-substituted cyclopropylcarbonyl, cyclobutylcarbonyl, Cyclcopentylcarbonyl, cyclohexylcarbonyl, Cyclopropylmethylcarbonyl, Cyclobutylmethylcarbonyl, Cyclopentylmethylcarbonyl cyclohexylmethylcarbonyl, cyclopropylsulfonyl, Cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, Cyclopropylmethylsulfonyl, Cyclobutylmethylsulfonyl, Cyclopentylmethylsulfonyl or cyclohexylsulfonyl, or 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 are substituted),
R ^{3 represents} hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine,
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
Z 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 compounds of the formula (IiA) in which R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings given above as being particularly preferred.

The compounds of formula (Iii) and their preparation are in WO 96/35679 described; 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 with 1 to 6 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio,
R ³ furthermore represents cycloalkyl having 3 to 8 carbon atoms optionally substituted by cyano, fluorine, chlorine, bromine or C ₁ -C ₄ alkyl,
R ³ furthermore represents phenyl, naphthyl, benzyl, phenylethyl, thienyl, pyrazolyl, pyridinyl or quinolinyl,
where the following may be used as substituents:
Fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, C ₁ - C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -alkylthio, dimethylaminosulphonyl, diethylaminosulphonyl, respectively optionally fluorine and / or chlorine substituted C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl, each optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy substituted C ₁ -C ₄ alkoxycarbonyl or each optionally substituted 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, where the following may be used as substituents:
Fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulfonyl, diethylaminosulfonyl, each optionally substituted by fluorine and / or chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl or optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy-substituted 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 chlorine 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 represents oxygen or sulfur,
R ^{1 represents} hydrogen, cyano, fluorine or chlorine,
R ^{2 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 represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,
R ³ furthermore represents in each case 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, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, dimethylaminosulfonyl, 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 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, Dimethylaminosulfonyl or Diethylaminosulfonyl, each optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl , 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, each 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 formula (Iiii) and their preparation are in WO 00/02867 described; 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 - if n then 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 in each case optionally substituted aryl or arylalkyl each having 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 having 1 to 5 carbon atoms and at least one heteroatom (up 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, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ - Alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylamino, Di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylamino carbonyl, di (C ₁ -C ₄ alkyl) amino carbonyl, di (C ₁ -C ₄ alkyl) amino sulfonyl,
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 which has 1 to 6 carbon atoms and is optionally substituted by cyano, carboxy, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl,
R ² preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, 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 for 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 by 1 to 6 carbon atoms, for each optionally substituted by halogen alkenyl, alkenylcarbonyl, alkenylsulfonyl or alkynyl each having up to 6 carbon atoms, for each optionally substituted by halogen cycloalkylcarbonyl or cycloalkylsulfonyl each having 3 to 6 carbon atoms in the cycloalkyl groups, for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ - C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl 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 the alkyl part, or for each optionally nitro, cyano, halogen, C ₁ -C ₄ - alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ - alkyl-carbonyl, C ₁ -C ₄ -alkoxy-carbonyl or di- (C ₁ -C ₄ alkylamino) 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 methylene, ethane-1,1-diyl (ethylidene), ethane-1,2-diyl (dimethylene), propane-1,1-diyl (propylidene), propane, each optionally substituted by fluorine and / or chlorine -1,2-diyl or propane-1,3-diyl (trimethylene), cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1,1-diyl, cyclopentane-1,1-diyl or Cyclohexane-1,1-diyl, or - if n is 1 - also for a single bond, or is linked to Ar via a 1,2-ethanediyl (dimethylene) grouping;
Ar particularly preferably represents phenyl, naphthyl, benzyl, 1-phenyl-ethyl, 2-phenyl-ethyl, 1-phenyl-propyl, 2-phenyl-propyl or 3-phenyl-propyl or optionally substituted heterocyclyl or heterocyclylalkyl from the series oxiranyl, oxiranylmethyl, oxetanyl, Oxetanylmethyl, furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl, benzofuryl, Benzofurylmethyl, dihydrobenzofuryl, Dihydrobenzofurylmethyl, benzothienyl, benzothienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, pyranyl , Pyranylmethyl, 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-, 1-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl , n- or i-Propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethyl -amino, 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 chlorine,
R ⁵ particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or 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 optionally substituted by fluorine and / or chlorine , n-, i-, s- or t-butylsulfonyl, for ethenyl, propenyl, butenyl, ethenylcarbonyl, propenylcarbonyl, butenylcarbonyl, ethynyl, propynyl or butinyl, each optionally substituted by fluorine, chlorine and / or bromine, each optionally substituted by fluorine, Chlorine and / or bromine substituted cyclopropylcarbonyl, cyclopropylmethylcarbonyl, cyclobutylcarbonyl, cyclobutylmethylcarbonyl, cyclopentylcarbonyl, cyclopentylmethylcarbonyl, cyclohexylcarbonyl, cyclohexylmethylcarbonyl, cyclopropylsulfonyl, cyclopropylmethylsulfonyl, cyclobut ylsulfonyl, cyclobutylmethylsulfonyl, cyclopentylsulfonyl, cyclopentylmethylsulfonyl, cyclohexylsulfonyl or cyclohexylmethylsulfonyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-propyl, n-, i-, s- or t-propyl 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, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl or propyloxy, nyloxy, nyloxy, methoxycarbonyl - or i-Propoxycarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl substituted benzoyl, phenylsulfonyl, phenylacetyl, phenylpropionyl, benzylsulfonyl or phenylethylsulfonyl, or for each optionally nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or iP ropyl, n-, 1-, 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, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, sulfonyl , Propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl-substituted heterocyclylcarbonyl or heterocyclylsulfonyl from the series furylcarbonyl, furylsulfonyl, thienylcarbonyl, pyrylsulfylylylylylylylsulfonyl, pyrienylsulfonylylylylylsulfonyl, pyrienylsulfonylsulfonyl, pyrenylsulfonylsulfonyl, pyrenylsulfonylsulfonyl, pyrienylsulfonylsulfonyl, pyrenylsulfonylsulfonyl , Pyriminylcarbonyl, pyrimidinylsulfonyl;
A very particularly preferably represents methylene, ethane-1,1-diyl (ethylidene) or ethane-1,2-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, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl 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-, 1-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl propoxycarbonyl.

The general or preferred areas listed above Residual definitions for the formulas (Ii), (Iii) and (Iiii) can be used with one another, i.e. also can be combined as desired between the specified preferred ranges.

According to the invention, preference is given to the compounds of the formulas (Ii), (Iii) and (Iiii), in which a combination of those listed above as preferred Meanings exist.

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

According to the invention, very particular preference is given to the compounds of the formulas (II) (Iii) and (Iiii), in which a combination of the above as very special meanings listed preferably is present.

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

In the definitions are the saturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl each 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 (Iiii) 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 more suitable Warmblood toxicity for systemic and non-systemic control of parasitic pests such as arthropods, preferably insects, arachnids, those in animal husbandry and animal breeding at home, farm, breeding, zoo, laboratory, Experimental and hobby animals and occur in their environment. You are there against all or individual stages of development of the pests as well as against resistant and normally sensitive types of pests are effective.

By fighting animal pests, diseases and their Transmission, deaths and reduced performance (e.g. in the production of Meat, milk, wool, skins, eggs) can be prevented, so that through the use the active ingredients a more economical and easier animal husbandry is possible in certain areas is only possible.

The preparations according to the invention are preferably used for combating of ectoparasites.

The above-mentioned ectoparasites include: tick ticks, leather ticks, 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 z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
From the order of the Mallophagida and the subordinates Amblycerina and Ischnocerina z. B. 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 z. B. 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 z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattella germanica, Supella spp.
From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata z. B. 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) z. B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. Pterolichus 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 B. 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 B. Chickens, geese, turkeys, ducks and fish such as B. 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 hamster, 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 ones Preparations enterally, parenterally, dermally, nasally, by treating the environment, too through feed through preparations or with the help of shaped articles containing active ingredients such as z. B. strips, plates, ribbons, collars, medallions, ear tags, Limb bands, marking devices.

The present invention also includes pharmaceutical preparations in Dosage units. This means that the formulations in the form of individual parts, e.g. B. Tablets, coated tablets, capsules, pills, suppositories and ampoules are available, the Active substance content corresponds to a fraction or a multiple of a single dose. The dosage units can e.g. B. 1, 2, 3, or 4 or 1/2, 1/3, or 1/4 one Single dose included. A single dose preferably contains the amount of active ingredient which is administered in one application.

The enteral application of the active ingredients happens, for. B. orally in the form of powders, Suppositories, tablets, dragees, pills, suspensions, emulsions, capsules, waterings, Granules, drenches, pastes, boluses, medicated feed or drinking water. In the A feed through application is administered orally to the animal. Doing so z. B. the majority of the active ingredient is not absorbed and only comes after the passage through the animal in its excretion to effect. As Preparations may be mentioned here for example controlled release systems such as. B. Microcapsules, 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 Carriers contain, such as a) fillers and extenders, for. B. starches, milk sugar, Cane sugar, glucose, mannitol and silica, b) binders, e.g. B. Carboxymethyl cellulose, alginates, gelatin, polyvinyl pyrrolidone, c) humectants, e.g. B. Glycerin, d) disintegrants, e.g. B. agar, calcium carbonate and sodium carbonate, e) solution delay, e.g. B. paraffin and 1) absorption accelerator, e.g. B. quaternary ammonium compounds, g) wetting agents, e.g. B. cetyl alcohol, Glycerol monostearate, h) adsorbent, e.g. B. kaolin and bentonite and i) lubricants, e.g. B. Talc, calcium and magnesium stearate and solid polyethylene glycols or Mixtures of the substance classes mentioned under a) - i).

The tablets, coated tablets, pills, capsules, boluses and granules can be used with the usual coatings and casings, optionally containing opacifying agents be provided and also be composed so that they are the active ingredient (s) possibly only or preferably in a certain part of the intestinal tract give up delayed, as embedding compounds, e.g. B. polymer substances and Waxes can be used.

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

Medicated feed is made by mixing, pulling premixes in and on Feed mixtures or feed pellets obtained. Premixes contain the one or more Active ingredients diluted with extenders, such as. B. rock flour, starches, celluloses, Proteins and mixtures, binders, e.g. B. cellulose and derivatives, vegetable and animal fats and oils.

Suppositories can be the usual water-soluble in addition to the active ingredient (s) or contain water-insoluble carriers, e.g. B. polyethylene glycols, fats, e.g. B. Cocoa fat and higher esters (e.g. C14 alcohols with C16 fatty acids) or mixtures of these substances.

In addition to the active ingredient (s), powders and sprays can contain the usual carriers included, e.g. B. milk sugar, silicates (calcium, magnesium and / or aluminum e.g. Talc), silica, aluminum hydroxide, calcium carbonates, starches and their Derivatives, celluloses and their derivatives and polymaid powder or mixtures thereof Substances. Sprays can additionally contain solvents, emulsifiers, wetting agents, the below are named by way of example and conventional blowing agents, e.g. B. chlorinated hydrocarbons, short chain aliphates e.g. B. propane, butane and mixtures thereof.

In addition to the active ingredient (s), ointments, pastes, creams and gels can be the usual ones Carriers contain z. b. animal and vegetable fats, waxes, paraffins, starch and their derivatives, tragacanth, cellulose derivatives, polyethylene glycols, silicones, Bentonites, silica, talc and zinc oxide, acrylates or mixtures of these substances.

In addition to the active ingredient (s), solutions and emulsions can be the usual ones Contain carriers such as solvents, solubilizers and emulsifiers. Examples are given below.

The parenteral application happens for. B. in the form of injection (intramuscular, subcutaneously, intravenously, intraperitoneally) through solutions, emulsions, suspensions or by shaped bodies such. B. implants z. B. from biodegradable Polmeren consist.

For parenteral administration, the solutions and emulsions can also be used in sterile and blood isotonic form.

Suitable preparations for transdermal application are known Solutions containing active ingredients, which may contain substances that promote absorption. absorption accelerators Substances include 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 also contain the usual excipients such as liquid diluents, e.g. B. water, propylene glycol, suspending agents, e.g. B. ethoxylated isostearyl alcohols, polyethylene sorbitol and sorbitan esters, microcrystalline Cellulose, aluminum hydroxide, bentonite, agar and tragacanth or mixtures contain these substances.

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

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

Systemic parasite control on animals has generally been found proven to be advantageous, amounts of about 0.5 to 100 mg of active ingredient / kg of body weight to give good effect.

Dermal application is a suitable method for combating Ectoparasites and happens e.g. B. 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. B. aerosols, powder sprays, pump sprays, spot on, pour on solutions for direct application, infusion formulations, gels;
Emulsions and suspensions for dermal use and solid or semi-solid preparations;
Formulations in which the active ingredient is processed in an ointment base or in an oil in water or water in oil emulsion base;
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 any additives such as solubilizers, acids, bases, Buffer salts, antioxidants, preservatives can be added.

The following may be mentioned as solvents: water, alkanols, glycols, polyethylene glycols, Polypropylene glycols, glycerin, 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, N-methylpyrrolidone, 2-dimethyl-4-oxy-methylene-1,3-dioxolane.

If appropriate, the active compounds can also be used in physiologically acceptable form dissolve vegetable or synthetic oils.

The following may be mentioned as solubilizers: solvents, the solution of the active ingredient in Promote major solvents or prevent them from failing. 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 use thickeners in the preparation of the solutions inflict. Thickeners are: inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as Cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and Methacrylates.

Gels that are applied or spread on the skin are made by using solutions prepared as described above with so much Thickeners are added to form a clear mass with an ointment-like consistency arises. The thickeners specified above are used Thickeners used.

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

Pour-on formulations are made by adding the active ingredient in suitable Skin-compatible solvents or solvent mixtures dissolved, suspended or is emulsified. If necessary, other auxiliaries such as dyes, Antioxidants, light stabilizers, adhesives added.

Dyes are all dyes approved for use on animals that are dissolved or can be 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. B. substances from the class of benzophenones or Novantisol acid.

Adhesives are e.g. B. cellulose derivatives, starch derivatives, polyacrylates, natural Polymers such as alginates, gelatin.

Emulsions are either water in oil or oil in water.

They are made by either the active ingredient in the hydrophobic or in dissolves the hydrophilic phase and this with the help of suitable emulsifiers and optionally other auxiliaries such as dyes, preservatives, Antioxidants, light stabilizers, viscosity increasing substances, with the solvent of the homogenized in another phase.

The following may be mentioned as 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 _8-12 or other specially selected natural fatty acids, partial glyceride mixtures saturated or unsaturated, possibly also hydroxyl-containing fatty acids, mono- and diglycerides of C ₈ / C ₁₀ 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 ₁₂ chain chains C ₁₈ , isopropyl stearate, oleic acid oleic acid, oleic acid decyl ester, ethyl oleate, lactic acid ethyl ester, waxy fatty acid esters such as dibutyl phthalate, adipic acid diisopropyl ester, the latter related ester mixtures and other fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetyl stearyl alcohol.

Fatty acids such as B. oleic acid and its mixtures.

The following are mentioned as the hydrophilic phase:
Water, alcohols such as B. propylene glycol, glycerin, sorbitol and their mixtures.

The following may be mentioned as emulsifiers: nonionic surfactants, e.g. B. 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 ether orthophosphoric acid ester monoethanolamine salt;
cationic surfactants such as cetyltrimethylammonium chloride.

The following may be mentioned as further auxiliaries: viscosity-increasing agents and the emulsion stabilizing substances 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 listed substances.

Suspensions are made by placing 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 suspended.

All homogeneous solvents and Called solvent mixtures.

The surfactants specified above may be mentioned as wetting agents (dispersants).

Further additives mentioned are those mentioned above.

Semi-solid preparations for dermal administration differ from those above Suspensions and emulsions described only because of their higher viscosity.

The active ingredient is used with suitable carriers to produce solid preparations optionally mixed with the addition of auxiliaries and into the desired shape brought.

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

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

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

Ready-to-use preparations contain the active substance in concentrations of 1 ppm -80 weight percent, preferably from 0.01-65 weight percent. preferred Active substance amounts are 1 to 50 percent by weight, the amounts in the range 5 up to 40 percent by weight are to be preferred.

Preparations that are diluted before use contain the active ingredient in Concentrations of 0.5-90 percent by weight, preferably from 1 to 50 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 this deliver more effective results.

The non-systemic application via molded articles and Powder. Shapes are u. a. Collars, pendants for collars (medallions), Ear tags, tapes for attachment to limbs or body parts, adhesive strips and films, peel-off films. Powder forms are mentioned above.

In general, it has proven advantageous to use solid according to the invention Formulations, the 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 patient to be treated Release the animal over a period of at least three months to achieve good results To apply effectiveness.

Thermoplastic and flexible materials are used to manufacture the molded articles thermosetting plastics as well as elastomers and thermoplastic elastomers. As such may be mentioned polyvinyl resins, polyurethanes, polyacrylates, epoxy resins, Cellulose, cellulose derivatives, polyamides and polyesters with the above active ingredient are sufficiently tolerated. The polymers must have sufficient strength and Have flexibility so as not to crack or become brittle during molding. she must be of sufficient durability to withstand normal wear and tear his. In addition, the polymers must undergo sufficient migration of the active ingredient allow the surface of the molded body.

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 are used to manufacture the molded articles based on polyvinyl resin suitable, which is usually used to soften solid vinyl resins become. 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. Others can 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 complex linear polyesters, polymeric plasticizers and epoxidized soybean oils be used. The amount of the plasticizer is about 10 to 50% by weight, preferably about 20 to 45% by weight of the total composition.

Further constituents, such as stabilizing agents, Lubricants, fillers and coloring materials, may be included without the basic properties of the composition are changed. suitable Stabilizers are antioxidants and agents that protect the tapes ultraviolet radiation and unwanted degradation during processing, such as Protect extrusion presses. Some stabilizers, such as epoxidized soybeans, are used also as a secondary plasticizer. As lubricants, for example Stearates, stearic acid and low molecular weight polyethylenes are used become. These components can be present in a concentration up to about 5% by weight entire composition can be used.

In the production of the molded articles based on vinyl, the various Components mixed by known methods and by known extrusion or Injection molding process.

The choice of the processing method for the production of the shaped body is directed technically basically according to the rheological properties of the strip material and the shape of the desired band. The processing methods can be according to the Processing technology or according to the type of shape. at In terms of process technology, the processes can be classified according to the ones they run through subdivide rheological conditions. Then come for viscous tape materials Casting, pressing, injection molding and application and for elastoviscose polymers Injection molding, extrusion (extrusion), calendering, rolling and possibly edges in question. Divided according to the type of shape, the invention can be Moldings 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 the In principle, the explanations given above for other polymers are exemplary for Polyvinyl resins were made.

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

The following should be noted in this context:
Polyisocyanates containing isocyanurate groups, such as, for. B. in US-PS 3 001 973, in DE-PS 10 22 789, 12 22 067 and 10 27 394 and in DE-OSes 19 29 034 and 20 04 048 are described; Polyisocyanates containing urethane groups, such as z. B. be described in DE-PS 752 261 or in US-PS 3 394 164; polyisocyanates containing acylated urea groups according to DE-PS 12 30 778; Polyisocyanates containing biuret groups, such as, for. B. in DE-PS 11 01 394, in US-PS 31 24 605 and 32 01 372, and in GB-PS 889 050 are described; Polyisocyanates produced by telomerization reactions, such as, for. Described in U.S. Patent 3,654,106; Polyisocyanates containing ester groups, such as, for. B. in GB-PSen 965 474 and 10 72 956, in US-PS 3 567 763 and in DE-PS 12 31 688; Reaction products of the above-mentioned isocyanates with acetals according to DE-PS 10 72 385 and polyisocyanates containing polymeric fatty acid residues according to US Pat. No. 3,455,883.

It is also possible to use the Distillation residues 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 Diphenylmethane.

Also polyhydroxyl compounds already containing urethane or urea groups and optionally modified natural polyols, such as castor oil, carbohydrates or starch, polyester amides and polyamides include e.g. B. from multi-valued saturated and unsaturated carboxylic acids or their anhydrides and polyvalent saturated and unsaturated amino alcohols, diamines, polyamines and their Mixtures of predominantly linear condensates can be used for this purpose. Also adducts of alkylene oxides with phenol-formaldehyde resins or Urea-formaldehyde resins can also be used according to the invention.

Representatives of these compounds are e.g. B. in High Polymers, Vol. XVI, "Polyurethane, Chemistry and Technology ", written by Saunders-Frisch, Interscience Publishers, New York, London, Volume I, 1962, pages 32-42 and Pages 44-54 and Volume II, 1964, Pages 5-6 and 198-199, as well as in the plastic manual, volume VII, Vieweg- Höchtlen, Carl Hanser Verlag, Munich, 1966, z. B. on pages 45-71, described.

Of course, mixtures of the above-mentioned compounds with at least two isocyanate-reactive hydrogen atoms with one Molecular weight of 400-10,000, e.g. B. mixtures of polyethers used become.

When choosing the one used for the production of the polyurethane High molecular weight polyol component should be noted that the finished polyurethane in water should not be swellable. The use of a surplus Polyhydroxyl compounds with ethylene oxide units (polyethylene glycol polyether or polyester with diethylene or triethylene glycol as the diol component) should therefore be avoided.

Thermoplastic materials are particularly emphasized for the production of the shaped bodies Elastomers. These are materials that have elastomeric phases in thermoplastic processable polymers either physically mixed in or chemically bound contain. A distinction is made between polymer blends in which the elastomeric phases Are part of the polymeric framework. By building the thermoplastic Elastomers are hard and soft areas side by side. Form the hard areas a crystalline network structure or a continuous phase thereof Interstices of elastomeric segments are filled. Because of this structure these materials have rubber-like properties.

• 1. Copolyester
• 2. Polyether-Block-Amide (PEBA)
• 3. Thermoplastische Polyurethane (TPU)
• 4. Thermoplastische Polyolefine (TPO)
• 5. Styrol-Block Copolymere

There are 5 main groups of thermoplastic elastomers:

• 1. Copolyester
• 2. Polyether Block Amides (PEBA)
• 3. Thermoplastic Polyurethane (TPU)
• 4. Thermoplastic polyolefins (TPO)
• 5. Styrene block copolymers

Suitable copolyesters (segmented polyester elastomers) are composed, for example, of a large number of recurring, short-chain ester units and long-chain ester units which are combined by ester linkages, 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 (III)


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 2 239 271, DOS 2 213 128, DOS 2 449 343 and US-P 3 023 192 are known.

Suitable copolyesters are e.g. B. under the trade name ®Hytrel from Du Pont, ®Pelpren from Toyobo®, Arnitel from Akzo, ®Ectel from Eastman Kodak and ®Riteflex available 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 radicals of compounds which stop the polymerization.

The dicarboxylic acid polyamides with the terminal carboxyl groups are on get known way, such. B. by polycondensation of one or more lactams or / and one or more amino acids, further by polycondensation of one Dicarboxylic acid with a diamine, each in the presence of an excess of one organic dicarboxylic acid, preferably with terminal carboxyl groups. This Carboxylic acids become part of the polyamide chain during polycondensation and attach themselves in particular to the end of the same, whereby an α-ω- receives dicarboxylic acid polyamide. Furthermore, the dicarboxylic acid acts as Chain terminator, which is why it is also used in excess.

The polyamide can be obtained from lactams and / or amino acids with a hydrocarbon chain consisting of 4-14C atoms, such as. B. from Caprolactam, oenantholactam, dodekalactam, undekanolactam, decanolactam, 11-amino undecanoic or 12-aminododecanoic acid.

As examples of polyamides, such as those obtained by polycondensation of a dicarboxylic acid a diamine can be called the condensation products Hexamethylenediamine with adipic, azelaic, sebacic, and 1,12-dodecanedioic acid, and the condensation products of nonamethylene diamine and adipic acid.

In the case of those for the synthesis of the polyamide, that is, on the one hand for fixing each one Carboxyl group at each end of the polyamide chain and on the other hand as Chain terminators used in dicarboxylic acid come in those with 4-20C atoms Question, especially alkanedioic acids, such as amber, adipic, cork, azelaic, sebacic, Undecanedioic or dodecanedioic acid, also 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 2C atoms. In particular, these are polyoxyethylene, polyoxypropylene and polyoxytetramethylene glycol, and copolymers thereof.

The average molecular weight of these OH groups terminated Polyoxyalkylene glycols can move in a wide range, advantageously between 100 and 6000, especially between 200 and 3000.

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

Processes for the synthesis of such PEBA polymers are known from FR-PS 7 418 913 (No. of 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, are particularly suitable described, are constructed statistically. Suitable and preferred suitable PEBA Polymers are e.g. B. under the trade name ®PEBAX from Atochem, ®Vestamid the 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 substances is preferably 1 to 50%; preferred in the case of medallions, pendants and ear tags at 2.5 to 35%, in the case of foils, adhesive strips preferably at 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 compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, sprays, for. B. aerosols or pump sprays, fine encapsulation in polymeric materials, paints and ULV cold and warm mist formulations.

These formulations are prepared in a known manner, e.g. B. by mixing of the active substances with extenders, i.e. liquid solvents, under pressure liquefied gases and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In case of using water as Extenders can e.g. B. also used organic solvents as auxiliary solvents become. 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, e.g. B. petroleum fractions, Alcohols, such as butanol or glycol, and 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. With liquefied gaseous extenders or carriers are meant such liquids which are gaseous at normal temperature and pressure, e.g. B. Aerosol Propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and Carbon dioxide. Possible solid carriers are: B. natural stone powder, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or Diatomaceous earth and synthetic rock powder, such as highly disperse silica, Alumina and silicates. Possible solid carriers for granules are: B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, Dolomite and synthetic granules from inorganic and organic flours as well as granules of organic material such as sawdust, coconut shells, Corn cobs and tobacco stalks. As emulsifiers and / or foaming agents come in Question: e.g. B. nonionic and anionic emulsifiers, such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates. As dispersants come in Question: e.g. B. lignin sulfite and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and Metal phthalocyanine 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 Active ingredient, 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 ingredients (co- Active ingredients), such as. B. known fungicides, bactericides, acaricides, nematicides or Insecticides, so used e.g. B. to broaden the spectrum of activity or To prevent the development of resistance. In many cases you get synergistic Effects, d. H. the effectiveness of the mixture is greater than the effectiveness of the Individual components.

The co-active ingredients preferably include insecticides such as those containing phosphorus Connections, d. H. Phosphoric or phosphonic acid esters, natural or synthetic Pyrethroids, carbamates, amidines, juvenile hormones and juvenoid synthetic Agents.

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-diethyl-0-phenylglyoxylonitrile oxime thiophosphate (phoxime),
0.0-diethyl-0-cyanochlorobenzaldoxime thiophosphate (chlorophoxime),
0,0-diethyl-0- (4-bromo-2,5-dichlorophenyl) -phosphorothionat (bromophos-ethyl),
0,0,0 ', 0'-tetraethyl-S, S'-methylene-di (phosphorodithionate) (ethion),
2,3-p-Dioxanedithiol-S, S-bis (0,0-diethylphosphorodithionat,
2-chloro-1- (2,4-dichlorophenyl) vinyl diethyl phosphate (chlorfenvinphos),
0.0-Dimethyl-0- (3-methyl-4-methylthiophenyl) thionophosphoric acid ester (fenthion).

The carbamates include:
2-isopropoxyphenylmethyl carbamate (propoxur),
1-naphthyl-N-methyl carbamate (carbaryl).

The synthetic pyrethroids include compounds of the formula I.


in which
R ¹ and R ^{2 represent} halogen, optionally halogen-substituted alkyl, optionally halogen-substituted phenyl,
R ^{3 represents} hydrogen or CN,
R ^{4 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 ^{2 represents} halogen, in particular fluorine, chlorine, bromine, trihalomethyl, phenyl, chlorophenyl,
R ^{3 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 represents} 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 ^{4 represents} fluorine in the 4-position,
R ^{5 represents} hydrogen.

The following may be mentioned in detail:
3- [2- (4-chlorophenyl) -2-chlorovinyl] -2,2-dimethyl-cyclopropanecarboxylic acid [(α-cyano-4-fluoro-3-phenoxy) benzyl] ester (flumethrin),
2,2-dimethyl-3- (2,2-dichlorovinyl) -cyclopropanecarboxylic acid-α-cyano (4-fluoro-3-phenoxy) -benzyl ester (cyfluthrin) and its enantiomers and stereomers,
α-cyano-3-phenoxybenzyl (±) -cis, trans-3- (2,2-dibromovinyl) -2,2-dimethylcyclopropane carboxylate (deltamethrin),
2,2-dimethyl-3- (2,2-dichlorovinyl) -cyclopropanecarboxylic acid-α-cyano-3-phenoxybenzyl ester (cypermethrin),
3-phenoxybenzyl (±) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropane carboxylate (permethrin),
α- (p-Cl-phenyl) isovaleric acid α-cyano-3-phenoxybenzyl ester (Fenvalerate),
2-Cyano-3-phenoxybenzyl-2- (2-chloro-α, α, α-trifluoro-p-toluidino) -3-methylbutyrate (fluvalinate).

The amidines include:
3-Methyl-2- [2,4-dimethyl-phenylimino] -thiazoline,
2- (4-chloro-2-methylphenylimino) -3-methylthiazolidine,
2- (4-chloro-2-methylphenylimino) -3- (isobutyl-1-enyl) -thiazolidine
1,5-bis- (2,4-dimethylphenyl) -3-methyl-1,3,5-triazapenta-1,4-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:

The substituted diaryl ethers include, in particular, substituted alkoxydiphenyl ethers or diphenyl methanes 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 indicated for R ¹ ,
R ^{4 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 represents pyridyl or pyridazinyl which are optionally substituted by fluorine, chlorine, methyl, NO ₂ , methoxy, methylmercapto,
X stands for O,
Y stands for O,
Z represents O, CH ₂ or - (CH ₃ ) ₂ -,
m represents 1,
n stands for 1.

The following connections are specifically mentioned:

Benzoylureas include compounds of the formula (V):


in which
R ^{1 represents} halogen,
R ^{2 represents} hydrogen or halogen,
R ^{3 represents} hydrogen, halogen or C _1-4 alkyl,
R ^{4 is} halogen, 1-5 haloC _1-4 alkyl, C _1-4 alkoxy, 1-5 haloC _1-4 alkoxy, C _1-4 alkylthio, 1-5 halogen -C _1-4 alkylthio, phenoxy or pyridyloxy which may optionally be substituted by halogen, C _1-4 alkyl, 1-5 halogen C _1-4 alkyl, C _-4 alkoxy, 1-5 halogen -C _1-4 alkoxy, C _1-4 alkylthio, 1-5 haloC ₁ -C ₄ alkylthio.

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, Bioethanomifhrin, Bethenomifhrin, Bethenomifhrin, Bethanomifhrin , Butocarboxime, butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Chromafenozide, Cis-Resmethrin, Clofocytoprene, Cofocenthrin, Cofocenthrin, Cofocenthrin, Cofocenthrin , Cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Dicofol, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,
Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Eprinomectin, Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Fluthrinoxin, Fluutinoxin, Fluutinoxin , Fubfenprox, Furathiocarb,
granulosis
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
nucleopolyhedroviruses
Lambda cyhalothrin, lufenuron
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron
Omethoate, oxamyl, oxydemethone M
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
quinalphos,
ribavirin
Salithion, Sebufos, Selamectin, Silafluofen, Spinosad, Spirodic1ofen, Sulfotep, Sulprofos,
Tau-fluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, tetradifon Thetacypermethrin, thiacloprid, thiamethoxam, Thiapronil, Thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate , Triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii
YI 5302
Zeta-cypermethrin, zolaprofos
(1R-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-tetramethylcyclopropanecarboxylat
1 - [(2-Chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1 H) - imine
2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazol
2- (Acetlyoxy) -3-dodecyl-1,4-naphthalenedione
2-chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] -benzamide
2-chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino-carbonyl] -benzamide
3-methylphenyl propylcarbamate
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene
4-Chloro-2- (1,1-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-dichlorophenyl) -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-dichlorophenyl) -2-oxo-1-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-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide
N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine
N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbothioamid
N-methyl-N'-2-propenyl-1,2-hydrazindicarbothioamid
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) propoxy] benzene

Also a mixture with other known active ingredients, such as growth regulators is possible.

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

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. For manufacturing purposes a suitable formulation, the active ingredient solution is diluted with water on the desired concentration.

About 20 Lucilia cuprina larvae are placed in a test tube, which contains 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 substance 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-inhibiting effect

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

Solvent: dimethyl sulfoxide (DMSO)

In order to produce a suitable formulation, 20 mg of active ingredient with 1 ml DMSO produced a suitable drug solution. The solution thus obtained diluted with water to the desired concentration.

200 μl of this active ingredient preparation are placed in 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 single-use tubes of 2.0 cm ³ , mixed homogeneously and dried overnight. A spatula tip of sieved flea eggs (from artificially infected cats) is placed on top.

The effectiveness of the drug preparation is up to 1S times the development time of the control approach determined every 2 days by the approaches on Developmental stages of the fleas are examined.

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 (6)

1. Connections a) of the formula (Ii)


in which
R ^{1 represents} hydrogen or halogen,
R ^{2 represents} the grouping below,


wherein
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 ^{3 represents} formyl or an optionally substituted alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl, arylcarbonyl, arylalkylcarbonyl, aryloxycarbonyl, arylsulfonyl, heterocyclylsulfonyl or heterocyclyl
R ^{3 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


wherein
R ^{5 represents} hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, alkylcarbonyl or alkoxycarbonyl, or represents amino or hydroxy (in each case only bound to N), or a) 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 ^{4 represents} in each case optionally substituted cycloalkyl, aryl or heteroaryl,
R ^{5 represents} hydrogen, halogen or optionally substituted alkyl or alkoxy,
R ^{6 represents} optionally substituted alkyl and
R ^{7 represents} hydrogen, hydroxyl, amino or optionally substituted alkyl, alkoxy, alkenyl or alkynyl, or a) 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 represents} cyano, carbamoyl, thiocarbamoyl, halogen, or in each case optionally substituted alkyl or alkoxy, and
R ^{6 stands} for hydrogen or for optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkynyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, arylalkylcarbonyl, arylalkylsulfonyl, heterocycylcyclyllylcarbonyl to fight parasites on animals and in their environment. 2. Agents containing compounds of the formulas (Ii), (Iii) and / or (Iiii) and pharmaceutically acceptable carriers and / or auxiliary substances. 3. Use of compounds of the formulas (Ii), (Iii) and / or (Iiii) for Control of parasites on animals and / or in their environment. 4. Use according to claim 3 for combating ectoparasites. 5. Use of compounds of the formulas (Ii), (Iii) and / or (Iiii) according to Claim 1 for the preparation of agents for controlling parasites Animals and / or in their environment. 6. Procedures for controlling parasites on and / or in animals Environment in which the animals receive an effective amount of a compound of the formulas (Ii), (Iii) and / or (Iiii) according to claim 1.