Compositions comprising C-13 alkoxyether macrolide compounds and phenylpyrazole compounds

1. A compound of the formula (II):

wherein:

R 14 represents —(CH 2 ) s —O—Z

wherein,

s is 1 or 2;

Y represents —CH(OR 15 )—, —C(═O)— or —C(═NOR 15 );

R 15 represents hydrogen, alkyl or phenyl; and

R 16 represents —CH 3 or —CH 2 CH 3 ;

Z is alkenyl, alkynyl, alkanoyloxy, alkoxycarbonyl, alkenoyl, alkynoyl, or aroyl.

2. The compound of claim 1 , wherein:

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkenyl or alkynyl.

3. The compound of claim 1 , wherein:

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkoxycarbonyl, alkenoyl, alkynoyl, or aroyl.

4. The compound of claim 1 , wherein:

R 14 represents —(CH 2 ) s —O—Z

wherein,

s is 1;

Y represents —CH(OR 15 )—;

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkenyl, alkynyl, alkoxycarbonyl or aroyl.

5. The compound of claim 1 , which has the formula (IIa) wherein:

wherein:

R 14 represents —(CH 2 ) s —O—Z

wherein,

s is 1 or 2;

Y represents —CH(OR 15 )—, —C(═O)— or —C(═NOR 15 );

R 15 represents hydrogen, C 1 -C 4 alkyl or phenyl; and

R 16 represents —CH 3 or —CH 2 CH 3 ;

Z is alkenyl, alkynyl, alkanoyloxy, alkoxycarbonyl, alkenoyl, alkynoyl, or aroyl.

6. The compound of claim 5 wherein:

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkenyl or alkynyl.

7. The compound of claim 5 wherein:

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkoxycarbonyl, alkenyl, alkynoyl, or aroyl.

8. The compound of claim 5 wherein :

R 14 represents —(CH 2 ) s —O—Z

wherein,

s is 1;

Y represents —CH(OR 15 );

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkenyl, alkynyl, alkoxycarbonyl or aroyl.

9. The compound of claim 1 , which has the formula (IIb):

wherein:

R 14 represents —(CH 2 ) s —O—Z

wherein,

s is 1 or 2;

Y represents —CH(OR 15 )—, —C(═O)— or —C(═NOR 15 );

R 15 represents hydrogen, C 1 -C 4 alkyl or phenyl; and

R 16 represents —CH 3 or —CH 2 CH 3 ;

Z is alkenyl, alkynyl, alkanoyloxy, alkoxycarbonyl, alkenoyl, alkynoyl, or aroyl.

10. The compound of claim 9 wherein:

Z is alkenyl or alkynyl.

11. The compound of claim 9 wherein:

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkoxycarbonyl, alkenoyl, alkynoyl, or aroyl.

12. The compound of claim 9 , wherein:

wherein:

R 14 represents —(CH 2 ) s —O—Z

wherein,

s is 1;

Y represents —CH(OR 15 );

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkenyl, alkynyl, alkoxycarbonyl or aroyl.

13. A composition for the treatment of a parasite infestation in birds or mammals which comprises a pharmaceutically effective amount a compound of formula (II):

wherein:

R 14 represents —(CH 2 ) s —O—Z

wherein,

s is 1 or 2;

Y represents —CH(OR 15 )—, —C(═O)— or —C(═NOR 15 );

R 15 represents hydrogen, alkyl or phenyl;

R 16 represents —CH 3 or —CH 2 CH 3 ; and

Z is alkenyl, alkynyl, alkanoyloxy, alkoxycarbonyl, alkenoyl, alkynoyl, or aroyl;

a pharmaceutically effective amount of at least one compound of the formula (I)

wherein:

R 1 is a halogen, CN or alkyl;

R 2 is S(O) n R 3 , 4,5-dicyanoimidazol-2-yl or haloalkyl;

R 3 is alkyl or haloalkyl;

R 4 represents a hydrogen, halogen, NR 5 R 6 , S(O) m R 7 , C(O)R 7 , C(O)OR 7 , alkyl, haloalkyl, OR 8 radical or —N═C(R 9 )(R 10 ) radical;

R 5 and R 6 independently represent hydrogen, alkyl, haloalkyl, C(O)alkyl, S(O) r CF 3 , alkoxycarbonyl; or

R 5 and R 6 can together form a divalent alkylene radical which is optionally interrupted by one or two divalent heteroatoms;

R 7 represents an alkyl or haloalkyl;

R 8 represents an alkyl, haloalkyl or hydrogen;

R 9 represents an alkyl or hydrogen;

R 10 represents an optionally substituted aryl or an optionally substituted heteroaryl group;

R 11 and R 12 represent, independently of one another, hydrogen, halogen, CN or NO 2 ;

R 13 represents a halogen, haloalkyl, haloalkoxy, S(O) q CF 3 or SF 5 ;

m, n, q and r represent, independently of one another, an integer equal to 0, 1 or 2;

X represents a trivalent nitrogen atom or a C—R 12 radical, the three other valencies of the carbon atom forming part of the aromatic ring; and

a pharmaceutically acceptable carrier.

14. The composition of claim 13 , wherein in formula (II):

Y represents —CH(OR 15 )—;

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is alkenyl, alkanoyloxy, alkoxycarbonyl or aroyl.

15. The composition of claim 13 , wherein in formula (I):

R 1 is CN or C 1 -C 4 alkyl;

R 2 is S(O) n R 3 ;

R 3 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 4 represents NR 5 R 6 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 8 radical;

R 5 and R 6 independently represent hydrogen, C 1 -C 4 alkyl, or C(O)alkyl;

R 7 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 8 represents C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or hydrogen;

R 11 and R 12 represent, independently of one another, hydrogen, or halogen;

R 13 represents a halogen, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, or SF 5 ; and

m, n, q and r represent, independently of one another, an integer equal to 0, 1 or 2.

16. The composition of claim 13 , wherein in formula (I):

R 1 is CN;

R 2 is S(O) n R 3 ;

R 3 is CF 3 ;

R 4 represents NR 5 R 6 ;

R 5 and R 6 independently represent hydrogen;

R 11 and R 12 represent Cl;

R 13 represents CF 3 ;

n is 1 ; and

X represents C—R 12 ;

and wherein in formula (II):

Y represents —CH(OR 15 )—;

R 15 represents hydrogen, or C 1 -C 8 alkyl; and

Z is, alkanoyloxy or alkoxycarbonyl.

17. A spot-on or pour-on composition for the treatment of a parasite infestation in birds or mammals which comprises a pharmaceutically effective amount of the compound of formula (III):

wherein R 16 represents —CH 3 or —CH 2 CH 3 ;

a pharmaceutically effective amount of at least one compound of the formula (I):

wherein:

R 1 is CN;

R 2 is S(O) n R 3 ;

R 3 is CF 3 ;

R 4 represents NR 5 R 6 ;

R 5 and R 6 independently represent hydrogen;

R 11 and R 12 represent Cl;

R 13 represents CF 3 ;

n is 1; and

X represents C—R 12 ; and

a pharmaceutically acceptable liquid carrier.

18. The composition of claim 13 or 17 , which further comprises at least one additional macrocyclic lactone compound.

19. The composition of claim 18 , which further comprises a cestodal agent.

20. The composition of claim 19 , wherein the one additional macrocyclic lactone compound is eprinomectin and the cestodal agent is praziquantel.

21. The composition of claim 13 , which further comprises a nitroguanidine or pyridylmethylamine insecticide.

22. The composition of claim 21 , wherein the nitroguanidine or pyridylmethylamine insecticide is imidacloprid.

23. A method for the treatment of a parasitic infestation in a bird or mammal which comprises administering a pharmaceutically effective amount of the composition of claim 13 or 17 .

24. The method of claim 23 , wherein the mammal is a dog or cat.