Anti-bacterial compositions containing certain 3-nitropyrazoles
AssigneeEli Lilly and Company
InventorsReuben G. Jones, Norman H. Terando
Life of this patent
Estimating the term…
Abstract
Novel 1,4-disubstituted-3-nitropyrazoles having antimicrobial, parasiticidal, and herbicidal activity are prepared by a reaction sequence of which the individual steps are conventional. The new 3-nitropyrazoles are characterized by a 1-substituent and a usually carbonyl-containing 4-substituent. The novel 3(5)-nitro-4-pyrazole-carbonitrile is obtained as an intermediate in the preparation of the biologically-active compounds. Preferred compounds are 1-alkyl or -alkenyl-4-pyrazolecarboxamides and carbonitriles. The new compounds are particularly useful for the control of bacterial animal diseases.
Claims30
An antibacterial composition which comprises a physiologically-acceptable inert carrier and an antibacterially-effective amount of a compound of the formula ##STR18## wherein R represents A. C.sub.3 -C.sub.4 epoxyalkyl,
- B. hydrogen,
- C. c.sub.1 -c.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, cyclopropylmethyl, C.sub.3 -C.sub.10 cycloalkenyl, C.sub.2 -C.sub.10 alkyl mono- or disubstituted with halo or C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.10 alkyl monosubstituted with
- 1. mercapto,
- 2. carboxamido,
- 3. keto oxygen,
- 4. hydroxy,
- 5. phthalimido,
- 6. C.sub.1 -C.sub.3 alkylthio,
- 7. C.sub.1 -C.sub.3 alkylsulfonyl,
- 8. C.sub.1 -C.sub.3 alkanoyl,
- 9. phenyl,
- 10. phenyl monosubstituted with
- a. C.sub.1 -C.sub.3 alkyl,
- b. C.sub.1 -C.sub.3 haloalkyl,
- c. hydroxy, or
- d. halo, ##STR19## wherein R.sup.1 represents a. C.sub.1 -C.sub.3 alkyl,
- b. C.sub.1 -C.sub.3 alkoxy,
- c. C.sub.1 -C.sub.3 haloalkyl,
- d. amino,
- e. C.sub.3 -C.sub.6 cycloalkyl,
- f. phenoxy,
- g. phenyl, or
- h. phenyl monosubstituted with
- 1. C.sub.1 -C.sub.3 alkyl,
- 2. C.sub.1 -C.sub.3 haloalkyl,
- 3. halo, or
- 4. hydroxy, or
- 12. cyano, or
- D. 4-nitrophenyl, 5-nitro-2-thiazolyl, or 3-nitro-2-pyridyl;
- and
- X represents
- A. 5-methylamino-1,3,4-thiadiazol-2-yl,
- B. cyano, ##STR20##
- wherein R.sup.2 represents 1. hydrogen, or
- 2. C.sub.1 -C.sub.6 alkyl;
- or ##STR21## wherein R.sup.3 represents C.sub.1 -C.sub.6 alkyl;
- provided that a C.sub.1 alkyl R group is substituted only with phenyl or substituted phenyl.
An antibacterial composition which comprises a physiologically-acceptable inert carrier and an antibacterially-effective amount of 1,1'-(2,5-cyclohexadien-1,4-ylene)-bis-(3-nitro-4-pyrazolecarboxamide).
Dependencies are inferred from the claim text.