Claims
- 1. A compound of formula (I), ##STR30## wherein: X is halogen, nitro, or unsubstituted or halo-substituted alkylsulfenyl, alkylsulfinyl or alkylsulfonyl, wherein the alkyl moiety is a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- Y is hydrogen, halogen, cyano, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, amino, alkylamino, dialkylamino, trialkylammonium salt, cyanoalkylamino, alkoxyalkylamino, alkoxycarbonylamino, alkylcarbonylamino, haloalkylcarbonylamino, alkylaminocarbonylamino, dialkylaminocarbonylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- Z is cyano or halogen; and
- R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are each individually hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl and alkoxy moieties; and with the proviso that at least one of R.sub.2 to R.sub.5 is other than hydrogen.
- 2. The compound of claim 1 of formula (I), wherein X is S(O).sub.n R.sub.1, having a formula (II), ##STR31## wherein: Y is hydrogen, halogen, cyano, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, amino, alkylamino, dialkylamino, trialkylammonium salt, cyanoalkylamino, alkoxyalkylamino, alkoxycarbonylamino, alkylcarbonylamino, haloalkylcarbonylamino, alkylaminocarbonylamino, dialkylaminocarbonylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- R.sub.1 is a linear or branched alkyl of one to four carbon atoms, which is substituted by one or more halogen atoms, which are the same or different, up to full substitution of the alkyl group;
- n is 0, 1 or 2; and
- R.sub.2 and R.sub.4 are each individually hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl and alkoxy moieties; and with the proviso that one of R.sub.2 and R.sub.4 is other than hydrogen.
- 3. The compound of claim 2 of formula (II), having a formula (IIa), wherein:
- Y is amino, alkylamino, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, alkoxyalkylamino, alkylcarbonylamino, haloalkylcarbonylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- R.sub.2 is hydrogen or halogen;
- R.sub.4 is hydrogen, halogen, haloalkyl or haloalkoxy, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl and alkoxy moieties; and
- with the proviso that one of R.sub.2 and R.sub.4 is other than hydrogen.
- 4. The compound of claim 3 of formula (IIa), having a formula (IIb), wherein:
- Y is amino, alkylamino, alkoxymethylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties contain one or two carbon atoms;
- R.sub.1 is trifluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl;
- R.sub.2 is bromine, chlorine or fluorine; and
- R.sub.4 is bromine, chlorine, fluorine, trifluoromethyl or trifluoromethoxy.
- 5. The compound of claim 4, having a formula (IIb), which is:
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-dichlorofluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-ethoxymethylamino-3-cyano-4-dichlorofluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-difluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-dichlorofluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-methylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-methylsulfinylpyrazole; or
- 1-[2-(3,5-dichloro)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfenylpyrazole.
- 6. A compound of formula (III), ##STR32## wherein: Z is C.sub.1-4 alkoxycarbonyl, aminocarbonyl or cyano; and
- R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are each individually hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl and alkoxy moieties; and with the proviso that at least one of R.sub.2 to R.sub.5 is other than hydrogen.
- 7. A compound of formula (IV), ##STR33## wherein: Z is C.sub.1-4 alkoxycarbonyl or aminocarbonyl;
- X is halogen, nitro, or unsubstituted or halo-substituted alkylsulfenyl, alkylsulfinyl or alkylsulfonyl, wherein the alkyl moiety is a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety; and
- R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are each individually hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl and alkoxy moieties; and with the proviso that at least one of R.sub.2 to R.sub.5 is other than hydrogen.
- 8. A compound of formula (V), 21, 25, or 22, ##STR34## wherein: Y is hydrogen, halogen, cyano, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, amino, alkylamino, dialkylamino, trialkylammonium salt, cyanoalkylamino, alkoxyalkylamino, alkoxycarbonylamino, alkylcarbonylamino, haloalkylcarbonylamino, alkylaminocarbonylamino, dialkylaminocarbonylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- Z is cyano or halogen; and
- R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are each individually hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl and alkoxy moieties; and with the proviso that at least one of R.sub.2 to R.sub.5 is other than hydrogen.
- 9. The compound of any one of claims 6, 7 or 8 wherein:
- Y is amino, alkylamino, alkoxymethylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties contain one or two carbon atoms;
- R.sub.2 is bromine, chlorine or fluorine;
- R.sub.3 and R.sub.5 are each hydrogen; and
- R.sub.4 is bromine, chlorine, fluorine, trifluoromethyl or trifluoromethoxy.
- 10. A method for the control of: arthropods; nematodes; or helminth or protozoan pests at a locus which comprises treatment of the locus with an effective amount of a compound of formula (I), ##STR35## wherein: X is halogen, nitro, or unsubstituted or halo-substituted alkylsulfenyl, alkylsulfinyl or alkylsulfonyl, wherein the alkyl moiety is a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- Y is hydrogen, halogen, cyano, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, amino, alkylamino, dialkylamino, trialkylammonium salt, cyanoalkylamino, alkoxyalkylamino, alkoxycarbonylamino, alkylcarbonylamino, haloalkylcarbonylamino, alkylaminocarbonylamino, dialkylaminocarbonylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- Z is cyano or halogen; and
- R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are each individually hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl and alkoxy moieties; and with the proviso that at least one of R.sub.2 to R.sub.5 is other than hydrogen.
- 11. The method of claim 10 of the compound of formula (I), having a formula (IIb), ##STR36## Y is amino, alkylamino, alkoxymethylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties contain one or two carbon atoms;
- R.sub.1 is trifluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl;
- n is 0, 1 or 2;
- R.sub.2 is bromine, chlorine or fluorine; and
- R.sub.4 is bromine, chlorine, fluorine, trifluoromethyl or trifluoromethoxy.
- 12. The method of claim 11, wherein the compound of formula (IIb) is:
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-dichlorofluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-ethoxymethylamino-3-cyano-4-dichlorofluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-difluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-dichlorofluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-methylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-methylsulfinylpyrazole; or
- 1-[2-(3,5-dichloro)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfenylpyrazole.
- 13. The method of claim 10, wherein the locus comprises agricultural or horticultural plants or a medium in which the plants grow and the pests are arthropod or nematode pests of the plants, and the treatment is by applying to the plants or to the medium in which they grow an effective amount of the compound of formula (I).
- 14. The method of claim of 13, wherein the compound is applied to the locus, in which the arthropod or nematode pests are controlled, at a rate of about 0.005 kg to about 15 kg of compound per hectare of locus treated.
- 15. The method of claim 14, wherein the compound is applied to the locus at a rate of about 0.02 kg to about 2 kg of compound per hectare.
- 16. The method of claim 13, wherein said pests are mites, aphids, insects or plant nematodes or combinations thereof, which comprises incorporating the compound into soil in which the plants are planted or are to be planted, or applying the compound to the plant's seeds, to the plant's roots, or to the plant's foliage.
- 17. The method of claim 16, wherein: said insects are soil insects in the Coleoptera order, Lepidoptera order or Diptera order or foliar insects in the Lepidoptera order, Coleoptera order, Homoptera order or Thysanoptera order; said mites are in the subclass Acari; and said aphids are in the Homoptera order.
- 18. The method of claim 10, wherein said method is employed in the field of veterinary medicine or livestock husbandry or in the maintenance of public health against arthropods, helminths or protozoa which are parasitic internally or externally upon warm-blooded vertebrates.
- 19. The method of claim 18, wherein said arthropods are insects in the Diptera order or mites in the subclass Acari or both.
- 20. A composition for the control of arthropod, nematode, helminth, or protozoan pests comprising; an agronomically acceptable carrier and an effective amount of a compound of formula (I), ##STR37## wherein: X is halogen, nitro, or unsubstituted or halo-substituted alkylsulfenyl, alkylsulfinyl or alkylsulfonyl, wherein the alkyl moiety is a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- Y is hydrogen, halogen, cyano, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, amino, alkylamino, dialkylamino, trialkylammonium salt, cyanoalkylamino, alkoxyalkylamino, alkoxycarbonylamino, alkylcarbonylamino, haloalkylcarbonylamino, alkylaminocarbonylamino, dialkylaminocarbonylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halosubstitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl moiety;
- Z is cyano or halogen; and
- R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are each individually hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro, wherein the alkyl and alkoxy moieties are a linear or branched chain, containing one to four carbon atoms, and the halo-substitution consists of one or more halogen atoms, which are the same or different, up to full substitution of the alkyl and alkoxy moieties; and with the proviso that at least one of R.sub.2 to R.sub.5 is other than hydrogen.
- 21. The composition of claim 20, which contains 0.05 to 95% by weight of one or more compounds of formula (I) as active ingredient and 1 to 95% by weight of one or more agronomically or medicinally acceptable solid or liquid carriers.
- 22. The composition of claim 21, further comprising 0.5 to 50% by weight of one or more compatible components, which are agronomically or medicinally acceptable diluents, adjuvants or surface active-agents.
- 23. The composition of claim 20 wherein the compound of formula (I) has a formula (IIb), ##STR38## Y is amino, alkylamino, alkoxymethylamino or alkoxyalkylideneimino, wherein the alkyl and alkoxy moieties contain one or two carbon atoms;
- R.sub.1 is trifluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl;
- n is 0, 1 or 2;
- R.sub.2 is bromine, chlorine or fluorine; and
- R.sub.4 is bromine, chlorine, fluorine, trifluoromethyl or trifluoromethoxy.
- 24. The composition of claim 23, wherein the compound of formula (IIb) is:
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-chlorodifluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-dichlorofluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-ethoxymethylamino-3-cyano-4-dichlorofluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfenylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-difluoromethylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-dichlorofluoromethylsulfonylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-methylsulfinylpyrazole;
- 1-[2-(3-chloro-5-trifluoromethyl)pyridyl]-5-amino-3-cyano-4-methylsulfinylpyrazole; or
- 1-[2-(3,5-dichloro)pyridyl]-5-amino-3-cyano-4-trifluoromethylsulfenylpyrazole.
Parent Case Info
This is a continuation of co-pending application Ser. No. 07/643,530, filed on Jan. 18, 1991, now abandoned.
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Continuations (1)
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Number |
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643530 |
Jan 1991 |
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