Phosphonoureide and phosphonothioureide anthelmintics

Claim 2

A compound of the formula (I): ##STR105## wherein A is a divalent arylene group selected from phenylene, naphthalene, anthrylene or phenanthrylene or a divalent heterocyclic group selected from diazepinylene, pyridinylene, pyrimidylene, triethylene or furylene, substituted with (a) vicinal alkylenedioxy of from 1 to 4 carbon atoms; or (b) a group of the formula: R 1 (A') a wherein R 1 is (1) a substituted or unsubstituted 5 or 6 membered heterocyclic group, having as hetero atom, oxygen, sulfur or nitrogen, or any combination of these wherein the total number of hetero atoms does not exceed three; or (2) an unsubstituted or substituted heterocyclic-alkyl group, wherein the heterocyclic group is as defined in (1) above and the alkyl group contains from 1 to 4 carbon atoms; A' is oxygen, sulfur, sulfinyl, sulfonyl or carbonyl; and a is an integer of 0 to 1; R is (a) hydrogen; (b) (C 1 -C 10 ) alkyl; (c) (C 1 -C 10 ) haloalkyl; (d) (C 3 -C 6 ) cycloalkyl; (e) (C 2 -C 11 ) alkoxyalkyl; (f) (C 1 -C 10 ) cyanoalkyl; (g) (C 13 -C 6 ) alkenyl; (h) (C 3 -C 6 ) haloalkenyl; (i) (C 13 -C 6 ) alkynyl; (j) (C 13 -C 6 ) haloalkynyl; (k) benzyl; or (l) phenyl; Y is R', OR', N(R') 2 or SR' and Y' is OR', N(R') 2 or SR' wherein R' is an aliphatic group of from 1 to 18 carbon atoms, or a substituted or unsubstituted (C 6 -C 10 ) aromatic group; X is oxygen or sulfur; X' is oxygen or sulfur; and Z is a group of the formula: ##STR106## wherein R and R 1 are as defined above; n is an integer of 0 to 1; B is carbonyl, sulfinyl, or sulfonyl; Q is alkylene of from 2 to 4 carbon atoms; X" is oxygen or sulfur, provided that when X" is sulfur, X is oxygen; and X'" is oxygen or sulfur, and Y and Y' are as above defined.

Claim 3

A compound of the formula (I): ##STR107## wherein A is a divalent heterocycle group selected from diazepinylene, pyridinylene, pyrimidylene, thienylene or furylene, optionally substituted with: (a) halogen; (b) cyano; (c) nitro; (d) di(C 1 -C 18 ) alkylamino; (e) vicinal alkylene of from 2 to 6 carbon atoms; (f) vicinal alkylenedioxy of from 1 to 4 carbon atoms; or (g) a group of the formula R 1 (A') a wherein R 1 is (1) an aliphatic group of from 1 to 18 carbon atoms; (2) a substituted or unsubstituted aromatic group containing from 6 to 10 carbon atoms in the aromatic ring; (3) a substituted or unsubstituted 5 or 6 membered heterocyclic group which has as hetero atom, oxygen, sulfur or nitrogen, or any combination of these wherein the total number of hetero atoms does not exceed three; (4) a substituted or unsubstituted heterocyclic-alkyl group, wherein the heterocyclic group is as defined in (3) above and the alkyl group contains from 1 to 4 carbon atoms; A' is oxygen, sulfur, sulfinyl, sufonyl or carbonyl; and a is an integer of 0 to 1; R is (a) hydrogen; (b) (C 1 -C 10 ) alkyl; (c) (C 1 -C 10 ) haloalkyl; (d) (C 3 -C 6 ) cycloalkyl; (e) (C 2 -C 11 ) alkoxyalkyl; (f) (C 1 -C 10 ) cyanoalkyl; (g) (C 3 -C 6 ) alkenyl; (h) (C 3 -C 6 ) haloalkenyl; (i) (C 3 -C 6 ) alkynyl; (j) (C 3 -C 6 ) haloalkynyl; (k) optionally substituted aralkyl of up to 11 carbon atoms; or (l) substituted or unsubstituted (C 6 -C 10 ) aryl; Y is R', OR', N(R') 2 or SR' and Y' is OR', N(R') 2 or SR' wherein R' is an aliphatic group of from 1 to 18 carbon atoms, or a substituted or unsubstituted (C 6 -C 10 ) aromatic group; X is oxygen or sulfur; X' is oxygen or sulfur; and Z is a group of the formula: ##STR108## wherein R and R 1 are as defined above; n is an integer of 0 to 1; B is carbonyl, sulfinyl, or sulfonyl; Q is alkylene of from 2 to 4 carbon atoms; X" is oxygen or sulfur, provided that when X" is sulfur, and Y and Y' are as above defined, X is oxygen; and X'" is oxygen or sulfur.

Claim 4

A compound of the formula (I): ##STR107## wherein A is a divalent heterocycle group selected from diazepinylene, pyridinylene, pyrimidylene, thienylene or furylene, optionally substituted with: (a) halogen; (b) cyano; (c) nitro; (d) di(C 1 -C 18 ) alkylamino; (e) vicinal alkylene of from 2 to 6 carbon atoms; (f) vicinal alkylenedioxy of from 1 to 4 carbon atoms; or (g) a group of the formula R 1 (A') a wherein R 1 is (1) an aliphatic group of from 1 to 18 carbon atoms; (2) a substituted or unsubstituted aromatic group containing from 6 to 10 carbon atoms in the aromatic ring; (3) a substituted or unsubstituted 5 or 6 membered heterocyclic group which has as hetero atom, oxygen, sulfur or nitrogen, or any combination of these wherein the total number of hetero atoms does not exceed three; (4) a substituted or unsubstituted heterocyclic-alkyl group, wherein the heterocyclic group is as defined in (3) above and the alkyl group contains from 1 to 4 carbon atoms; A' is oxygen, sulfur, sulfinyl, sufonyl or carbonyl; and a is an integer of 0 to 1; R is (a) hydrogen; (b) (C 1 -C 10 ) alkyl; (c) (C 1 -C 10 ) haloalkyl; (d) (C 3 -C 6 ) cycloalkyl; (e) (C 2 -C 11 ) alkoxyalkyl; (f) (C 1 -C 10 ) cyanoalkyl; (g) (C 3 -C 6 ) alkenyl; (h) (C 3 -C 6 ) haloalkenyl; (i) (C 3 -C 6 ) alkynyl; (j) (C 3 -C 6 ) haloalkynyl; (k) optionally substituted aralkyl of up to 11 carbon atoms; or (l) substituted or unsubstituted (C 6 -C 10 ) aryl; Y is R', OR', N(R') 2 or SR' and Y' is OR', N(R') 2 or SR' wherein R' is an aliphatic group of from 1 to 18 carbon atoms, or a substituted or unsubstituted (C 6 -C 10 ) aromatic group; X is oxygen or sulfur; X' is oxygen or sulfur; and Z is a group of the formula: ##STR108## wherein R and R 1 are as defined above; n is an integer of 0 to 1; B is carbonyl, sulfinyl, or sulfonyl; Q is alkylene of from 2 to 4 carbon atoms; X" is oxygen or sulfur, provided that when X" is sulfur, and Y and Y' are as above defined, X is oxygen; and X'" is oxygen or sulfur.

Claim 5

An anthelmintic composition for oral administration comprising an anthelmintically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.

Claim 6

An anthelmintic composition for oral administration comprising an anthelmintically effective amount of the compound of claim 2 and a pharmaceutically acceptable carrier.

Claim 7

A method for combatting a helminth infection in a host animal which comprises administering an anthelmintically effective amount of a compound of claim 1 to said animal.

Claim 8

A method for combatting a helminth infection in a host animal which comprises administering an anthelmintically effective amount of a compound of claim 2 to said animal.