Thienyl-and furylpyrrole insecticidal and acaricidal agents

A compound having the structural formula ##STR117## wherein R, R.sub.1 and R.sub.2 are each independently hydrogen, halogen, NO.sub.2 or CHO, and when R.sub.1 and R.sub.2 are taken together with the carbon atoms to which they are attached, they may form a ring in which R.sub.1 R.sub.2 is represented by the structure:

• ##STR118## L, T, V and W are each independently hydrogen, halogen, CN or NO.sub.2 ;
• A is O or S;
• X is CN, NO.sub.2, C.sub.1 -C.sub.6 haloalkyl, S(O).sub.m CF.sub.2 R.sub.3 or C(S)NR.sub.4 R.sub.5 ;
• R.sub.3 is hydrogen, F, Cl, Br, CF.sub.2 H, CCl.sub.2 H, CClFH, CF.sub.3 or CCl.sub.3 ;
• m is an integer of 0, 1 or 2;
• R.sub.4 and R.sub.5 are each independently hydrogen,
• C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen atoms, or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• Y is hydrogen, halogen, C.sub.1 -C.sub.6 haloalkyl, S(O).sub.m CF.sub.2 R.sub.3, CN or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• Z is hydrogen, halogen or C.sub.1 -C.sub.6 haloalkyl;
• B is R.sub.6, OR.sub.6 or CN;
• R.sub.6 is hydrogen, C(O)R.sub.7, CHR.sub.8 NHC(O)R.sub.9, CH.sub.2 SQ,
• CHR.sub.10 OC(O) (CR.sub.11 R.sub.12).sub.n Q.sub.1,
• C.sub.1 -C.sub.6 alkyl optionally substituted with one to three halogen atoms,
• one tri(C.sub.1 -C.sub.4 alkyl)silyl,
• one hydroxy,
• one cyano,
• one or two C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one to three halogen atoms,
• one C.sub.1 -C.sub.4 alkylthio,
• one phenyl optionally substituted with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• one phenoxy group optionally substituted with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• one benzyloxy group optionally substituted on the phenyl ring with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• one C.sub.1 -C.sub.6 alkylcarbonyloxy group optionally substituted with one to three halogen atoms,
• one C.sub.2 -C.sub.6 alkenylcarbonyloxy group optionally substituted with one to three halogen atoms,
• one phenylcarbonyloxy group optionally substituted with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• one C.sub.1 -C.sub.6 alkoxycarbonyl group optionally substituted with one to three halogen atoms or one to three C.sub.1 -C.sub.4 alkoxy groups, or
• one benzylcarbonyloxy group optionally substituted on the phenyl ring with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• C.sub.3 -C.sub.6 alkenyl optionally substituted with one to three halogen atoms or one phenyl group, or
• C.sub.3 -C.sub.6 alkynyl optionally substituted with one to three halogen atoms or one phenyl group;
• R.sub.7 is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl each optionally substituted with one to three halogen atoms,
• one hydroxy,
• one cyano,
• one or two C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one to three halogen atoms,
• one C.sub.1 -C.sub.4 alkylthio,
• one phenyl group optionally substituted with
• one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• one phenoxy group optionally substituted with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• one benzyloxy group optionally substituted on the phenyl ring with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• one C.sub.1 -C.sub.6 alkylcarbonyloxy group optionally substituted with one to three halogen atoms,
• one C.sub.2 -C.sub.6 alkenylcarbonyloxy group optionally substituted with one to three halogen atoms,
• one phenylcarbonyloxy group optionally substituted with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• one C.sub.1 -C.sub.6 alkoxycarbonyl group optionally substituted with one to three halogen atoms or one to three C.sub.1 -C.sub.4 alkoxy groups, or
• one benzyloxycarbonyl group optionally substituted on the phenyl ring with one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups or one to three C.sub.1 -C.sub.4 alkoxy groups,
• C.sub.2 -C.sub.6 alkenyl optionally substituted with one to three halogen atoms or one phenyl groups,
• C.sub.3 -C.sub.6 alkynyl optionally substituted with one to three halogen atoms or one phenyl group,
• phenyl optionally substituted with one or more halogen atoms, C.sub.1 -C.sub.4 alkyl groups, C.sub.1 -C.sub.4 alkoxy groups, phenoxy groups, C.sub.1 -C.sub.4 alkylthio groups, tri(C.sub.1 -C.sub.4 alkyl)silyl groups, C.sub.1 -C.sub.4 alkylsulfinyl groups, C.sub.1 -C.sub.4 alkylsulfonyl groups, CN groups, NO.sub.2 groups or CF.sub.3 groups,
• phenoxy optionally substituted with one or more halogen atoms, C.sub.1 -C.sub.4 alkyl groups, C.sub.1 -C.sub.4 alkoxy groups, C.sub.1 -C.sub.4 alkylthio groups, tri(C.sub.1 -C.sub.4 alkyl)silyl groups, C.sub.1 -C.sub.4 alkylsulfinyl groups, C.sub.1 -C.sub.4 alkylsulfonyl groups, CN groups, NO.sub.2 groups or CF.sub.3 groups,
• 1- or 2-naphthyl,
• 2-, 3-, or 4-pyridyl optionally substituted with one to three halogen atoms,
• C.sub.1 -C.sub.6 alkoxy optionally substituted with one to three halogen atoms, or
• C.sub.2 -C.sub.6 alkenyloxy optionally substituted with one to three halogen atoms;
• R.sub.8 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.9 is C.sub.1 -C.sub.6 alkyl optionally substituted with one to three halogen atoms,
• phenyl optionally substituted with one to three halogen atoms, CN groups, NO.sub.2 groups, C.sub.1 -C.sub.4 alkyl groups, C.sub.1 -C.sub.4 alkoxy groups or CF.sub.3 groups,
• 2- or 3-thienyl, or
• 2- or 3-furyl;
• ##STR119## CN, C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogen atoms, CN groups or phenyl groups, or
• phenyl optionally substituted with one or more halogen atoms, C.sub.1 -C.sub.4 alkyl groups, C.sub.1 -C.sub.4 alkoxy groups, CN groups, NO.sub.2 groups, CF.sub.3 groups or NR.sub.24 R.sub.25 groups;
• A.sub.1 is O or S;
• R.sub.13 is C.sub.1 -C.sub.6 alkyl or phenyl;
• R.sub.14 is C.sub.1 -C.sub.6 alkyl;
• R.sub.15 and R.sub.16 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl or may be taken together with the atom to which they are attached to form a 5- to 7-membered heterocyclic ring;
• R.sub.17 is C.sub.1 -C.sub.4 alkyl;
• R.sub.18 is hydrogen, C.sub.1 -C.sub.4 alkyl or may be taken together with either R.sub.19 or R.sub.21 and the atoms to which they are attached to form a 5- to 7-membered heterocyclic ring optionally substituted with one or two C.sub.1 -C.sub.4 alkyl groups;
• R.sub.19 and R.sub.20 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.21 is C.sub.1 -C.sub.4 alkyl or when taken together with R.sub.18 and the atoms to which they are attached may form a 5- to 7-membered heterocyclic ring optionally substituted with one or two C.sub.1 -C.sub.4 alkyl groups;
• R.sub.22 and R.sub.23 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl or when taken together may form a ring wherein R.sub.22 R.sub.23 is represented by --CH.dbd.CH--CH.dbd.CH--;
• R.sub.24 and R.sub.25 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.10 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.11 and R.sub.12 are each independently hydrogen,
• C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogen atoms,
• C.sub.1 -C.sub.6 alkoxy optionally substituted with one or more halogen atoms,
• C.sub.1 -C.sub.6 alkylthio optionally substituted with one or more halogen atoms, or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups;
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms, or
• when R.sub.11 and R.sub.12 are taken together with the atom to which they are attached may form a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted with one to three C.sub.1 -C.sub.4 alkyl groups, C.sub.2 -C.sub.6 alkenyl groups or phenyl groups, or R.sub.11 or R.sub.12 may be taken together with R.sub.26 and the atoms to which they are attached to form a 4- to 7-membered heterocyclic ring;
• n is an integer of 0, 1, 2, 3 or 4;
• Q.sub.1 is A.sub.2 R.sub.26, ##STR120## NR.sub.28 R.sub.29, CR.sub.30 R.sub.31 C(O)R.sub.32, or C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or more C.sub.1 -C.sub.6 alkyl groups,
• C.sub.2 -C.sub.6 alkenyl groups, or
• phenyl groups optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• A.sub.2 is O or S(O).sub.p ;
• p is an integer of 0, 1 or 2;
• R.sub.26 is hydrogen,
• C.sub.1 -C.sub.6 alkyl
• C.sub.2 -C.sub.6 alkenyl,
• C.sub.2 -C.sub.6 alkynyl,
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms,
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms,
• C(O)R.sub.33 provided p is O,
• C(O)R.sub.34 provided p is O,
• (CH.sub.2 CH.sub.2 O).sub.q R.sub.33, or ##STR121## R.sub.26 may be taken together with either R.sub.11 or R.sub.12 and the atoms to which they are attached to form a 4- to 7-membered heterocyclic ring;
• A.sub.3 is O or S;
• R.sub.33 is C.sub.1 -C.sub.6 alkyl,
• C.sub.2 -C.sub.6 alkenyl,
• C.sub.2 -C.sub.6 alkynyl, or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• q is an integer of 1, 2 or 3;
• R.sub.34 is OR.sub.37 or NR.sub.38 R.sub.39 ;
• R.sub.37 is C.sub.1 -C.sub.6 alkyl or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• R.sub.38 and R.sub.39 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.35 and R.sub.36 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl, or
• when taken together may form a ring wherein
• R.sub.35 R.sub.36 is represented by --CH.dbd.CH--CH.dbd.CH--;
• R.sub.27 is C.sub.1 -C.sub.4 alkyl;
• R.sub.28 is hydrogen,
• C.sub.1 -C.sub.6 alkyl,
• C.sub.2 -C.sub.6 alkenyl,
• C.sub.2 -C.sub.6 alkynyl, or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms, or
• R.sub.28 may be taken together with either R.sub.11 or R.sub.12 and the atoms to which they are attached to form a 4- to 7-membered heterocyclic ring;
• R.sub.29 is hydrogen,
• C.sub.1 -C.sub.6 alkyl,
• C.sub.2 -C.sub.6 alkenyl,
• C.sub.2 -C.sub.6 alkynyl,
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms,
• C(A.sub.4)R.sub.40,
• CN,
• SO.sub.2 R.sub.41, or
• C(O)CHR.sub.42 NHR.sub.43 ;
• A.sub.4 is O or S;
• R.sub.40 is OR.sub.44, CO.sub.2 R.sub.44, NR.sub.45 R.sub.46,
• C.sub.1 -C.sub.6 alkyl optionally substituted with one to three halogen atoms,
• C.sub.2 -C.sub.6 alkenyl,
• C.sub.2 -C.sub.6 alkynyl, or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• R.sub.44 is C.sub.1 -C.sub.6 alkyl optionally substituted with one phenyl group, or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• R.sub.45 and R.sub.46 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.41 is NR.sub.47 R.sub.48,
• C.sub.1 -C.sub.6 alkyl,
• C.sub.2 -C.sub.6 alkenyl,
• C.sub.2 -C.sub.6 alkynyl, or
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• R.sub.47 and R.sub.48 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.42 is hydrogen,
• C.sub.1 -C.sub.4 alkyl optionally substituted with one hydroxy group,
• one SR49 group,
• one C(O)NH.sub.2 group,
• one NH.sub.2 group,
• one NHC(.dbd.NH)NH.sub.2 group,
• one CO.sub.2 H group,
• one phenyl group optionally substituted with one hydroxy group,
• one 3-indolyl group or
• one 4-imidazolyl group;
• R.sub.49 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.43 is C(A.sub.4)R.sub.50 ;
• R.sub.50 is C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogen atoms,
• C.sub.1 -C.sub.6 alkoxyalkyl,
• C.sub.1 -C.sub.6 alkylthio,
• phenyl optionally substituted with one or more halogen atoms,
• NO.sub.2 groups,
• CN groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms,
• OR.sub.44,
• CO.sub.2 R.sub.44 or
• NR.sub.45 R.sub.46 ;
• R.sub.30 and R.sub.31 are each independently hydrogen,
• C.sub.1 -C.sub.6 alkyl optionally substituted with one or more halogen atoms,
• C.sub.1 -C.sub.6 alkoxy optionally substituted with one or more halogen atoms,
• C.sub.1 -C.sub.6 alkylthio optionally substituted with one or more halogen atoms,
• phenyl optionally substituted with one or more halogen atoms,
• CN groups,
• NO.sub.2 groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms, or
• when R.sub.30 and R.sub.31 are taken together with the atom to which they are attached may form a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted with one to three C.sub.1 -C.sub.4 alkyl groups, C.sub.2 -C.sub.6 alkenyl groups or phenyl groups;
• R.sub.32 is OR.sub.51, NR.sub.47 R.sub.48, C.sub.1 -C.sub.4 alkyl or
• phenyl optionally substituted with one or more halogen atoms,
• CN groups,
• NO.sub.2 groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• and
• R.sub.51 is C.sub.1 -C.sub.4 alkyl or
• phenyl optionally substituted with one or more halogen atoms,
• CN groups,
• NO.sub.2 groups,
• C.sub.1 -C.sub.4 alkyl groups optionally substituted with one or more halogen atoms, or
• C.sub.1 -C.sub.4 alkoxy groups optionally substituted with one or more halogen atoms;
• provided that when A is S, X is S(O).sub.m CF.sub.2 R.sub.3 and Z is hydrogen, then Y is hydrogen, halogen, C.sub.1 -C.sub.6 haloalkyl, S(O).sub.m CF.sub.2 R.sub.3 or CN;
• and further provided that when the pyrrole ring is substituted with hydrogen at each of the pyrrole carbon atoms adjacent to the ring nitrogen atom, then X cannot be CN or NO.sub.2.