3-(substituted phenyl)-5-(thienyl or furyl)-1, 2, 4-triazole compounds
OwnerJames T. Pechacek, Donald H. DeVries +8inventors
InventorsJames T. Pechacek, Donald H. DeVries, Francis E. Tisdell, Robert G. Suhr, Peter L. Johnson, Christopher J. Hatton, Maurice Chee Hoong Yap, Gary D. Stockdale, Christopher T. Hamilton, George W. Johnson
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Abstract
3-(Substituted phenyl)-5-(thienyl or furyl)-1,2,4-triazole compounds are useful as insecticides and acaricides. New synthetic procedures and intermediates for preparing the compounds, pesticide compositions containing the compounds, and methods of controlling insects and mites using the compounds are also provided.
Claims18
A compound of the formula (1) ##STR197## wherein Ar is substituted phenyl;
- Y is O or S;
- R.sup.2 is lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, or alkoxyalkyl;
- R.sup.3 is selected from H, halo, lower alkyl, (C.sub.7 -C.sub.21) straight or branched chain alkyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, alkoxyalkyl, alkoxyalkoxy, lower alkenyl, lower alkynyl, haloalkenyl, CN, NO.sub.2, COR.sup.6, CO.sub.2 R.sup.6, CON(R.sup.6).sub.2, (C.sub.3 -C.sub.6) cycloalkyl, S(O).sub.m R.sup.6, --OSO.sub.2 R.sup.6, SCN, --(CH.sub.2).sub.n R.sup.6, --CH.dbd.CHR.sup.6, --C.tbd.CR.sup.6, --(CH.sub.2).sub.q OR.sup.6, --(CH.sub.2).sub.q SR.sup.6, --(CH.sub.2).sub.q NR.sup.6 R.sup.6, --O(CH.sub.2).sub.q R.sup.6, --S(CH.sub.2).sub.q R.sup.6, --NR.sup.6 (CH.sub.2).sub.q R.sup.6, ##STR198## --Si(R.sup.7).sub.3 naphthyl, substituted naphthyl, phenyl, substituted phenyl;
- R.sup.4 and R.sup.5 are independently H, halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, CN, CO.sub.2 R.sup.6, CON(R.sup.6).sub.2, or S(O).sub.m alkyl, or
- if R.sup.4 and R.sup.5 are attached to adjacent carbon atoms, they may join to form a 5 or 6 member saturated or unsaturated carbocyclic ring which may be substituted by 1 or 2 halo, lower alkyl, lower alkoxy or haloalkyl groups;
- R.sup.6 is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;
- R.sup.7 is lower alkyl;
- m is 0, 1, or 2;
- n is 1 or 2;
- p is an integer from 2 to 6;
- and
- q is 0 or 1;
- or a phytologically acceptable acid addition salt thereof, where, in the foregoing definitions of R.sup.1 through R.sup.7,
- the term "lower alkyl" refers to (C.sub.1 -C.sub.6) straight hydrocarbon chains and (C.sub.3 -C.sub.6) branched and cyclic hydrocarbon groups;
- the terms "lower alkenyl" and "lower alkynyl" refer to (C.sub.2 -C.sub.6) straight hydrocarbon chains and (C.sub.3 -C.sub.6) branched hydrocarbon groups containing at least one double or triple bond, respectively;
- the term "lower alkoxy" refers to --O--lower alkyl;
- the terms "halomethyl" and "haloalkyl" refer to methoxy and lower alkyl groups substituted with one or more halo atoms;
- the terms "halomethoxy" and "haloalkoxy" refer to methyl and lower alkoxy groups substituted with one or more halo atoms;
- the term "alkoxyalkyl" refers to a lower alkyl group substituted with a lower alkoxy group;
- the term "alkoxyalkoxy" refers to a lower alkoxy group substituted with a lower alkoxy group;
- the term "substituted naphthyl" refers to naphthyl substituted with one or more groups independently selected from halo, halo (C.sub.1 -C.sub.4) alkyl, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, phenyl, (C.sub.1 -C.sub.4) alkoxy, or halo (C.sub.1 -C.sub.4) alkoxy;
- the term "substituted phenyl" refers to a phenyl group substituted with one or more groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyl, benzoyl, (C.sub.1 -C.sub.4) alkanoyloxy, (C.sub.1 -C.sub.4) alkoxycarbonyl, phenoxycarbonyl, or benzoyloxy;
- and
- the term "substituted benzenesulfonyl" refers to p-chlorobenzenesulfonyl and p-toluenesulfonyl.
A compound of the formula (1A) ##STR199## wherein R.sup.1 and R.sup.1' are independently H, Cl, F, methyl, halomethyl, methoxy, or halomethoxy;
- Y is O or S;
- R.sup.2 is lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, or alkoxyalkyl;
- R.sup.3 is selected from H, halo, lower alkyl, (C.sub.7 -C.sub.21) straight chain alkyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, alkoxyalkyl, alkoxyalkoxy, lower alkenyl, haloalkenyl, CN, NO.sub.2, CO.sub.2 R.sup.6, CON(R.sup.6).sub.2, (C.sub.3 -C.sub.6) cycloalkyl, S(O).sub.m R.sup.6, SCN, naphthyl, substituted naphthyl, phenyl, substituted phenyl, --(CH.sub.2).sub.n R.sup.6, --CH.dbd.CHR.sup.6, --C.tbd.CR.sup.6, --CH.sub.2 OR.sup.6, --CH.sub.2 SR.sup.6, --CH.sub.2 NR.sup.6 R.sup.6, --OCH.sub.2 R.sup.6, --SCH.sub.2 R.sup.6, --NR.sup.6 CH.sub.2 R.sup.6, ##STR200## R.sup.4 and R.sup.5 are independently H, halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, CN, CO.sub.2 R.sup.6, CON(R.sup.6).sub.2, or S(O).sub.m alkyl, or
- R.sup.4 and R.sup.5 form a 5 or 6 member saturated or unsaturated carbocyclic ring which may be substituted by 1 or 2 halo, lower alkyl, lower alkoxy or haloalkyl groups;
- R.sup.6 is H, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl;
- m is 0, 1, or 2;
- and
- n is 1 or 2;
- p is an integer from 2 to 6;
- or a phytologically acceptable acid addition salt thereof, where, in the foregoing definitions of R.sup.1 through R.sup.7,
- the term "lower alkyl" refers to (C.sub.1 -C.sub.6) straight hydrocarbon chains and (C.sub.3 -C.sub.6) branched and cyclic hydrocarbon groups;
- the terms "lower alkenyl" and "lower alkynyl" refer to (C.sub.2 -C.sub.6) straight hydrocarbon chains and (C.sub.3 -C.sub.6) branched hydrocarbon groups containing at least one double or triple bond, respectively;
- the term "lower alkoxy" refers to --O--lower alkyl;
- the terms "halomethyl" and "haloalkyl" refer to methoxy and lower alkyl groups substituted with one or more halo atoms;
- the terms "halomethoxy" and "haloalkoxy" refer to methyl and lower alkoxy groups substituted with one or more halo atoms;
- the term "alkoxyalkyl" refers to a lower alkyl group substituted with a lower alkoxy group;
- the term "alkoxyalkoxy" refers to a lower alkoxy group substituted with a lower alkoxy group;
- the term "substituted naphthyl" refers to naphthyl substituted with one or more groups independently selected from halo, halo (C.sub.1 -C.sub.4) alkyl, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, phenyl, (C.sub.1 -C.sub.4) alkoxy, or halo (C.sub.1 -C.sub.4) alkoxy;
- the term "substituted phenyl" refers to a phenyl group substituted with one or more groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyl, benzoyl, (C.sub.1 -C.sub.4) alkanoyloxy, (C.sub.1 -C.sub.4) alkoxycarbonyl, phenoxycarbonyl, or benzoyloxy;
- and
- the term "substituted benzenesulfonyl" refers to p-chlorobenzenesulfonyl and p-toluenesulfonyl.
A compound of formula (1B) wherein
- R.sup.1 and R.sup.1' are independently F or Cl;
- R.sup.2 is lower alkyl, and
- R.sup.3, R.sup.4 and R.sup.5 are independently H, Cl, or Br.
Dependencies are inferred from the claim text.