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Insecticidal N'-substituted-N,N'-disubstitutedhydrazines

  • US 6,013,836 A
  • Filed: 05/22/1995
  • Issued: 01/11/2000
  • Est. Priority Date: 02/28/1992
  • Status: Expired due to Term
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Assignments
First Claim
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1. A compound of the formula ##STR48## wherein X and X'"'"' are independently selected from O, S and NR, wherein R is selected from hydrogen and (C1 -C6)alkyl;

  • E is selected from;

    1) an unsubstituted tertiary-carbon containing (C4 -C10) alkyl or substituted tertiary-carbon containing (C3 -C10) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, and phenyl and wherein the sum of non-hydrogen atoms in E is from 4 to 14, E does not have a chain length of non-hydrogen atoms greater than 5, and E does not contain more than one cyano group; and

    2) an unsubstituted or substituted non-tertiary-carbon containing (C4 -C10) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, phenyl, and trimethylsilyl and wherein the sum of non-hydrogen atoms in E is from 5 to 14, E does not have a chain length of non-hydrogen atoms greater than 5, and E does not contain more than one cyano group;

    A and B are independently selected from;

    1) unsubstituted or substituted naphthyl wherein the substituents are independently selected from 1 to 3 halo;

    nitro;

    (C1 -C4)alkoxy;

    (C1 -C4)alkyl; and

    amino;

    2) unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 5 halo;

    nitro;

    cyano;

    hydroxy;

    (C1 -C6)alkyl;

    (C1 -C6)haloalkyl;

    (C1 -C6)cyanoalkyl;

    (C1 -C6)hydroxyalkyl;

    (C1 -C6)alkoxy;

    (C1 -C6)haloalkoxy;

    (C1 -C6)alkoxy(C1 -C6)alkyl;

    (C1 -C6)alkoxy(C1 -C6)alkoxy;

    (C1 -C6)alkylthio(C1 -C6)alkoxy;

    (C1 -C6)alkanoyloxy(C1 -C6)alkyl;

    (C2 -C6)alkenyl optionally substituted with halo, cyano, (C1 -C4)alkyl, or (C1 -C4)alkoxy;

    (C2 -C6)alkenyloxy;

    (C2 -C6)alkenylcarbonyl;

    (C2 -C6)alkenyloxycarbonyloxy;

    (C2 -C6)alkynyl optionally substituted with halo or (C1 -C4)alkyl;

    carboxy;

    (C1 -C6)alkylcarboxy(C1 -C6)alkyl);

    (C1 -C6)alkylcarbonyl;

    (C1 -C6)haloalkylcarbonyl;

    (C1 -C6)alkoxycarbonyl;

    (C1 -C6)haloalkoxycarbonyl;

    (C1 -C6)alkanoyloxy (--OCOR);

    (C1 -C6)alkoxycarbonyl(C1 -C6)alkoxy;

    amino (--NRR'"'"');

    carboxamido (--CONRR'"'"');

    (C2 -C6)alkenylcarbonylamino;

    (C1 -C6)hydroxyalkylaminocarbonyl;

    aminocarbonyloxy (--OCONRR'"'"');

    amido (--NRCOR'"'"');

    alkoxycarbonylamino (--NRCO2 R'"'"');

    thiocyanato;

    isothiocyanato;

    (C1 -C6)thiocyanatoalkyl;

    (C1 -C6)alkylthio;

    sulfoxide (--S(O)R);

    sulfonyl (--SO2 R);

    alkylsulfonyloxy (--OSO2 R);

    sulfonamide (--SO2 NRR'"'"');

    alkylthiocarbonyl (--CSR);

    thioamido (--NRCSR'"'"');

    unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C1 -C4)alkyl, (C1 -C4)haloalkyl, (C1 -C4)alkoxy, carboxy, amino, (C1 -C4)alkylamino, and (C1 -C4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;

    unsubstituted or substituted phenoxy wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C1 -C4)alkyl, (C1 -C4)haloalkyl, (C1 -C4)alkoxy, carboxy, amino, (C1 -C4)alkylamino, and (C1 -C4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;

    unsubstituted or substituted benzoyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C1 -C4)alkyl, (C1 -C4)haloalkyl, (C1 -C4)alkoxy, carboxy, amino, (C1 -C4)alkylamino and (C1 -C4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;

    benzoyloxy(C1 -C6)alkyl;

    phenylthio(C1 -C6)alkyl wherein the phenyl ring is unsubstituted or substituted with 1 to 3 substituents independently selected from halo, cyano, nitro, (C1 -C4)alkyl, (C1 -C4)haloalkyl, (C1 -C4)alkoxy, carboxy, amino, (C1 -C4)alkylamino, and (C1 -C4)dialkylamino having independently the stated number of carbon atoms in each alkyl group;

    imino (--CR═

    N--R2) wherein R2 is selected from hydroxy, (C1 -C4)alkyl, (C1 -C4)alkoxy, amino (--NRR'"'"'), phenylamino, carbonyl (--COR), and benzoyl;

    acetylthiosemicarbazone;

    or when two adjacent positions on the phenyl ring are substituted with alkoxy groups, these groups, together with the carbon atoms to which they are attached, may be joined to form a 5 or 6 membered dioxolano or dioxano heterocyclic ring; and

    3) unsubstituted or substituted five-membered heterocycle selected from furyl, thienyl, triazolyl, pyrrolyl, isopyrrolyl, pyrazolyl, isoimidazolyl, thiazolyl, isothiazolyl, oxazolyl, and isooxazolyl wherein the substituents are independently selected from 1 to 3 halo;

    nitro;

    hydroxy;

    (C1 -C6)alkyl;

    (C1 -C6)alkoxy;

    carboxy;

    (C1 -C6)alkoxycarbonyl (--CO2 R);

    (C1 -C6)alkylcarboxy(C1 -C6)alkyl (--RCO2 R'"'"');

    carboxamido (--CONRR'"'"');

    amino (--NRR'"'"');

    amido (--NRCOR'"'"');

    (C1 -C6)alkylthio;

    or unsubstituted or substituted phenyl wherein the substituents are independently selected from one to three halo, nitro, (C1 -C6)alkyl, (C1 -C6)haloalkyl;

    (C1 -C6)alkoxy;

    (C1 -C6)haloalkoxy;

    carboxy, (C1 -C4)alkoxycarbonyl (--CO2 R);

    or amino (--NRR'"'"');

    wherein R, R'"'"' and R" are selected from hydrogen and (C1 -C6)alkyl;

    and agronomically acceptable salts thereof;

    provided that;

    1) when X and X'"'"' are O and A and B are unsubstituted phenyl, then E is other than 2-methylpropyl (--CH2 CH(CH3)2);

    3-methylbutyl (--CH2 CH2 CH(CH3)2);

    neopentyl (2,2-dimethylpropyl;

    --CH2 C(CH3)3) or cyclohexylmethyl (--CH2 C6 H11);

    or2) when X and X'"'"' are O, and A is unsubstituted phenyl or phenyl substituted with 1 to 2 substituents independently selected from (C1 -C6)alkyl and halo, and B is unsubstituted phenyl or phenyl substituted with 1 to 2 substituents independently selected from halo, nitro, and (C1 -C6)alkyl, then E is other than halo(C2 -C6)alkyl;

    or3) when X and X'"'"' are O, and E is t-butyl (--C(CH3)3), and A is unsubstituted phenyl, then B is other than 4-nitrophenyl;

    or4) when one of A and B is an unsubstituted or substituted five-membered heterocycle then the other of A and B is other than an unsubstituted or substituted five-membered heterocycle;

    or5) when A is phenyl substituted with from two to three substituents in the 2, 3, and 4 positions wherein the 3 substituent is (C1 -C6)alkoxy, the 2 substituent is selected from halo and (C1 -C6)alkyl, and, when substituted, the 4 substituent is (C1 -C6)alkyl then B is other than unsubstituted phenyl or phenyl substituted with from one to four substituents in the 2, 3, 4, and 5 positions wherein the 2 substituent is selected from halo, and (C1 -C6)alkyl and the 3, 4, and 5 substituents are independently selected from bromo, chloro, fluoro, and (C1 -C6)alkyl.

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