Insecticidal Substituted Amino Heterocyclic and Heteroaryl Derivatives

A compound of formula I:

• wherein
• A is —CHR5—, —CHR5CHR6—, —O—, —S(O)n—, —NR7—, —OCHR5—, —CHR5O—, —S(O)nCHR5—, —CHR5S(O)n—, —C(O)—, —C(S)— or —C(═NOR7)—;
• B is —CHR8—, —O— or —S(O)n—;
• n is an integer selected from 0, 1 and 2;
• R, R1, R2 and R3 are independently selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkylthio, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano, nitro, aryl, aryloxy, heteroaryl, alkoxyalkyl, alkoxyalkoxyalkyl, cycloalkyl, cyanoalkyl, formal, alkoxycarbonyl, acetyl, alkylcarbonyl, alkenylcarbonyl, dialkylphosphonato, SFS, amino, mono- and dialkylamino, cycloalkylamino, (cycloalkyl)(alkyl)amino, alkylthio, sulfonyl, alkylsulfonyl, haloalkylsulfonyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylthiocarbonyl and hydroxycarbonyl;
• Q is selected from:
• where
• R4 is taken together with the connecting atom in Q to form a double bond as in (D) and (E) or
• R4 and R9 are independently selected from hydrogen, cyano, nitro, arylalkyl, 2-oxazoline, 2-thiazoline, 2-imidazoline, —C(X)R10, —C(X)OR11, —C(X)SR11, —S(O)nR11, —C(X)NR12R13, —S(O)nNR12R13, —P(X)(OR14)(OR15), —P(X)(NR16R17)(NR18R19), —CHR20—X—R21, —CH═NR22 and —C(═NR31)(SR32);
• where X is oxygen or sulfur;
• R10 is hydrogen or alkyl;
• R11 is hydrogen, alkyl, haloalkyl, hydroxyalkyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, or —NR10CO2R10;
• R12 and R13 are independently selected from hydrogen, alkyl, haloalkyl, cycloalkyl, cyanoalkyl, aryl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, mono or dialkylaminocarbonylalkyl, aminoalkyl, mono or dialkylaminoalkyl and arylcarbonyl;
• R14 and R15 are independently selected from hydrogen, alkyl and haloalkyl;
• R16, R17, R18 and R19 are independently selected from hydrogen and alkyl;
• R20 is hydrogen or alkyl;
• R21 is alkyl, haloalkyl, —C(X)R23 or —P(X)(OR24)(OR25);
• R22 is hydrogen, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, cyano, pyridinyl or 2-thiazolinyl;
• R23 is hydrogen, alkyl or haloalkyl;
• R24 and R25 are independently selected from hydrogen, alkyl and haloalkyl;
• R31 and R32 are independently selected from hydrogen, alkyl, arylalkyl, —C(X)R10, —CO2R11, —S(O)nR11, —C(X)NR12R13, —S(O)nNR12R13, —P(X)(OR14)(OR15), —P(X)(NR16R17)(NR18R19) and —CHR20—X—R21;
• R5 is selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, aryl, cyano and nitro;
• R6 is selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, aryl, cyano and nitro;
• R7 is hydrogen or alkyl;
• R8 is hydrogen, halogen, alkyl, alkoxy or aryl;
• R30 is hydrogen, halogen or alkyl;
• and
• agriculturally acceptable salts thereof.

A compound of formula I;

• wherein
• A is —CHR5—, —CHR5CHR6—, —O—, —S(O)n—, —NR7—, —OCHR5—, —CHR5O—, —S(O)nCHR5—, —CHR5S(O)n—, —C(O)—, —C(S)— or —C(═NOR7)—;
• B is —CHR8—, —O— or —S(O)n—;
• n is an integer selected from 0, 1 and 2;
• R, R1, R2 and R3 are independently selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkylthio, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano, nitro, aryl, aryloxy, heteroaryl, alkoxyalkyl, alkoxyalkoxyalkyl, cycloalkyl, cyanoalkyl, formal, alkoxycarbonyl, acetyl, alkylcarbonyl, alkenylcarbonyl, dialkylphosphonato, SF5, amino, mono- and dialkylamino, cycloalkylamino, (cycloalkyl)(alkyl)amino, alkylthio, sulfonyl, alkylsulfonyl, haloalkylsulfonyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylthiocarbonyl and hydroxycarbonyl;
• Q is:
• where
• R4 is taken together with the connecting atom in Q to form a double bond;
• R9 is selected from hydrogen, cyano, nitro, arylalkyl, 2-oxazoline, 2-thiazoline, 2-imidazoline, —C(X)R10, —C(X)OR11, —C(X)SR11, —S(O)nR11—, —C(X)NR12R13, —S(O)nNR12R13, —P(X)(OR14)(OR15), —P(X)(NR16R17)(NR18R19), —CHR20—X—R21, —CH═NR22 and —C(═NR31)(SR32)—;
• where X is oxygen or sulfur;
• R10 is hydrogen or alkyl;
• R11 is hydrogen, alkyl, haloalkyl, hydroxyalkyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, or —NR10CO2R10;
• R12 and R13 are independently selected from hydrogen, alkyl, haloalkyl, cycloalkyl, cyanoalkyl, aryl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, mono or dialkylaminocarbonylalkyl, aminoalkyl, mono or dialkylaminoalkyl and arylcarbonyl;
• R14 and R15 are independently selected from hydrogen, alkyl and haloalkyl;
• R16, R17, R18 and R19 are independently selected from hydrogen and alkyl;
• R20 is hydrogen or alkyl;
• R21 is alkyl, haloalkyl, —C(X)R23 or —P(X)(OR24)(OR25);
• R22 is hydrogen, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, cyano, pyridinyl or 2-thiazolinyl;
• R23 is hydrogen, alkyl or haloalkyl;
• R24 and R25 are independently selected from hydrogen, alkyl and haloalkyl;
• R31 and R32 are independently selected from hydrogen, alkyl, arylalkyl, —C(X)R10, —CO2R11, —S(O)nR11, —C(X)NR12R13, —S(O)nNR12R13, —P(X)(OR14)(OR15), —P(X)(NR16R17)(NR18R19) and —CHR20—X—R21;
• R5 is selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, aryl, cyano and nitro;
• R6 is selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, aryl, cyano and nitro;
• R7 is hydrogen or alkyl;
• R8 is hydrogen, halogen, alkyl, alkoxy or aryl;
• R30 is hydrogen, halogen or alkyl;
• provided that when R9 is hydrogen then at least one of R, R1, R2 and R3 is other than hydrogen;
• and
• agriculturally acceptable salts thereof.

A compound of formula I:

• wherein
• A is —CHR5—, —CHR5CHR6—, —O—, —S(O)n—, —NR7—, —OCHR5—, —CHR5O—, —S(O)nCHR5—, —CHR5S(O)n—, —C(O)—, —C(S)— or —C(═NOR7)—;
• B is —CHR8—, —O— or —S(O)n—;
• n is an integer selected from 0, 1 and 2;
• R, R1, R2 and R3 are independently selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkylthio, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano, nitro, aryl, aryloxy, heteroaryl, alkoxyalkyl, alkoxyalkoxyalkyl, cycloalkyl, cyanoalkyl, formal, alkoxycarbonyl, acetyl, alkylcarbonyl, alkenylcarbonyl, dialkylphosphonato, SF5, amino, mono- and dialkylamino, cycloalkylamino, (cycloalkyl)(alkyl)amino, alkylthio, sulfonyl, alkylsulfonyl, haloalkylsulfonyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl-alkyl, alkylthiocarbonyl and hydroxycarbonyl;
• Q is selected from:
• where
• R4 and R9 are independently selected from hydrogen, cyano, nitro, arylalkyl, 2-oxazoline, 2-thiazoline, 2-imidazoline, —C(X)R10, —C(X)OR11, —C(X)SR11, —S(O)nR11—, —C(X)NR12R13, —S(O)nNR12R13, —P(X)(OR14)(OR15), —P(X)(NR16R17)(NR18R19), —CHR20—X—R21, —CH═NR22 and —C(═NR31)(SR32);
• where X is oxygen or sulfur;
• R10 is hydrogen or alkyl;
• R11 is hydrogen, alkyl, haloalkyl, hydroxyalkyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, or —NR10CO2R10;
• R12 and R13 are independently selected from hydrogen, alkyl, haloalkyl, cycloalkyl, cyanoalkyl, aryl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, mono or dialkylaminocarbonylalkyl, aminoalkyl, mono or dialkylaminoalkyl and arylcarbonyl;
• R14 and R15 are independently selected from hydrogen, alkyl and haloalkyl;
• R16, R17, R18 and R19 are independently selected from hydrogen and alkyl;
• R20 is hydrogen or alkyl;
• R21 is alkyl, haloalkyl, —C(X)R23 or —P(X)(OR24)(OR25);
• R22 is hydrogen, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, cyano, pyridinyl or 2-thiazolinyl;
• R23 is hydrogen, alkyl or haloalkyl;
• R24 and R25 are independently selected from hydrogen, alkyl and haloalkyl;
• R31 and R32 are independently selected from hydrogen, alkyl, arylalkyl, —C(X)R10, —CO2R11, —S(O)nR11, —C(X)NR12R13, —S(O)nNR12R13, —P(X)(OR14)(OR15), —P(X)(NR16R17)(NR18R19) and —CHR20—X—R21;
• R5 is selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, aryl, cyano and nitro;
• R6 is selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, aryl, cyano and nitro;
• R7 is hydrogen or alkyl;
• R8 is hydrogen, halogen, alkyl, alkoxy or aryl;
• R30 is hydrogen, halogen or alkyl;
• provided that i) when A is —CHR5— or —CHR5CHR6—, B is —CHR8—, R, R1, R2, R3, R5, R6 and R8 are independently selected from hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or alkylthio then at least one of R4 and R9 is other than hydrogen, and ii) when A is —OCHR5—, —CHR5O—, —S(O)nCHR5— or —CHR5S(O)n—, B is —CHR8—, Q is (F), R, R1, R2 and R3 are independently selected from hydrogen, halogen, alkyl, alkoxy, alkylthio and dialkylamino, R5 and R8 are independently selected from hydrogen and alkyl, then R4 is other than hydrogen;
• and
• agriculturally acceptable salts thereof.

A compound of formula IA:

• wherein
• A is —CHR5—, —CHR5CHR6—, —O—, —S(O)n—, —NR7—, —OCHR5—, —CHR5O—, —S(O)nCHR5—, —CHR5S(O)n—, —C(O)—, —C(S)— or —C(═NOR7)—;
• B is —CHR8—, —O— or —S(O)n—;
• n is an integer selected from 0, 1 and 2;
• R, R1, R2 and R3 are independently selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkylthio, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cyano, nitro, aryl, aryloxy, heteroaryl, alkoxyalkyl, alkoxyalkoxyalkyl, cycloalkyl, cyanoalkyl, formal, alkoxycarbonyl, acetyl, alkylcarbonyl, alkenylcarbonyl, dialkylphosphonato, SF5, amino, mono- and dialkylamino, cycloalkylamino, (cycloalkyl)(alkyl)amino, alkylthio, sulfonyl, alkylsulfonyl, haloalkylsulfonyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylthiocarbonyl and hydroxycarbonyl;
• X is oxygen or sulfur;
• and
• Y is chlorine, bromine, iodine, methanesulfonyloxy or p-toluenesulfonyloxy;
• provided that when A is —O—, —CHR5— or —CHR5CHR6—, B is —CHR8—, where R5, R6 and R8 are selected from hydrogen, alkyl, alkoxy, alkylthio, chlorine, bromine or iodine and X is oxygen then at least one of R, R1, R2 and R3 is other than hydrogen, alkyl, alkoxy, alkylthio, chlorine, bromine or iodine.