Patent CA-2005740-A1 (CA)
Title: Substituted semicarbazone arthropodicides
Inventor: DAUB JOHN P
IPC: A01N/
Filed: 1989-12-15
Abstract: TITLE SUBSTITUTED SEMICARBAZONE ARTHROPODICIDES                   ABSTRACT OF THE DISCLOSURE           Substituted semicarbazones, including all geometric and stereoisomers thereof, of the following formula, are useful as arthropodicides: 1.    A compound of the formula   wherein:            Q is                   ,                     ,     ,                       ,        ,             ,         ,        A  is (CH2)t, O, S(O)q, NR7, OCH2 or S(O)qCH2, wherein, each carbon individually can be substituted with 1 to 2 substituents selected from 1 to 2 halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C7 alkylcycloalkyl, C2-C4 alkoxycarbonyl, or phenyl optionally substituted with 1 to 3. substituent independently selected from w; R1 and R2 are independently R8, halogen, CN, NO2, N3, SCN, OR8, SR8, SOR8, SO2R8, NR8R9, C(O)R8, CO2R8, C(O)NR8Rg~ OC(O)R8, OC02R8, OC(O)NR8R9, NRgC(O)R8, NR9C(O)NR8R9, OSO2R8, NR9SO2R8, or when m is 2, R1 is optionally taken together to form a 5 or 6 membered fused ring as OCH2O, OCH2CH2O OR CH2CH2O     each of which is optionally substituted with 1 to 4 halogen atoms or 1 to 2 methyl groups, or when n is 2, R2 is optionally taken together to form a 5 or 6 membered fused ring as OCH2O, OCH2CH2O or CH2CH2O each of which can be substituted 1 to 4 halogens or 1 to 2 methyl groups; R2 being other than CH3 when R1, R3 and R4 are H and A is CH2; R3 is H, C1-C6 alkyl, C1-C6 haloalkyl, C4-C6 alkylcycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C6 alkoxyalkyl, C2-C6 cyanoalkyl, C3-C8 alkoxycarbonylalkyl, OR8, S(O)qR8, NR8R9, CN, CO2R8, C(O)R8, C(O)NR8R9, C(S)NR8R9, C(S)R8, C(S)SR8, phenyl optionally substituted with (R10)p or benzyl optionally substituted with 1 to 3 substituents independently selected from W or R3 is C3-C6 cycloalkyl optionally substituted with 1 to 2 halogens or 1 to 2 CH3; R4 is H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C6 alkoxyalkyl, C2-C6 cyanoalkyl, phenyl optionally substituted with (R10)p or benzyl optionally substituted with 1 to 3 substituents independently selected from W; R5 and R6 are independently H, C1-C22 alkyl, C2-C22 alkoxyalkyl, C2-C22 alkylcarbonyl, C2-C22 alkoxycarbonyl, C2-C22 haloalkyl carbonyl, C2-C22 haloalkoxycarbonyl, SR11, CHO, C1-C4 alkylsulfonyl, phenylsulfonyl optionally substituted with 1 to 3 substituents independently selected from W; C7-C15 phenoxycarbonyl optionally substituted with 1 to 3 substituents selected from W; C7-C15 phenylcarbonyl optionally substituted with 1 to 3 substituents independently selected from W; C(O)CO2C1 to C4 alkyl, C8-C12 benzyloxycarbonyl optionally substituted with 1 to 3 substituents independently selected from W; or R5 and R6 are independently phenyl optionally substituted with 1 to 3 substituents independently selected from W, or benzyl optionally substituted with 1 to 3 substituents independently selected from W; R7 is H, C1-C4 alkyl or phenyl optionally substituted with W; SR8, SOR8, SO2R8, C(O)R8, CO2R8, C(O)NR8R9, C(S)NR8R9, C(S)R8, C(S)OR8, P(O)(OR8)2, P(S)(OR8)2, P(O)(R3)OR8 or P(O)(R8)SR8; provided that when R7 is other than COR8, C(C))NR8R9 or C(S)NR8R9 then R8 is other than H; R8 is H, C1-C6 alkyl, C1-C6 haloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C6 alkoxyalkyl, C2-C6 alkylthioalkyl, C1-C6 nitroalkyl, C2-C6 cyanoalkyl, C3-C8 alkoxycarbonylalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W     or benzyl optionally substituted with 1 to 3 substituents independently selected from W; R9 is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or R8 and R9 is optionally taken together as (CH2)4, (CH2)5 or (CH2CH2OCH2CH2); R10 is R8, halogen, CN, NO2, N3, SCN, OR8, SR8, SOR8, SO2R8, NR8R9, COR8, CO2R8, CONR8R9, SO2NR8R9, OC(O)R8, OCO2R8, OC(O)NR8R9, NR9C(O)R8, NR9C(O)NR8R9, OSO2R8, NR9SO2R8 or when p is 2, R10 is optionally taken together to form a 5 or 6 membered fused ring as OCH2O, OCH2CH2O, or CH2CH2O each of which is optionally substituted with independently, 1 to 4 halogen atoms or 1 to 2 methyl groups; R11 is C1-C22 alkyl, C1-C22 haloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W, or R11 is NR12C(O)R13, NR12S(O)aR13, C(O)R13, N12R16, SR14,  ,   or  ;     R12 and R16 are independently selected from C1 -C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl, C3-C6 alkoxycarbonylalkyl, C4-C8 dialkylaminocarbonylalkyl, phenyl optionally substituted by 1 to 2 substituents selected from W, benzyl optionally substituted by 1 to 2 substituents selected from W and phenethyl optionally substituted by 1 to 2 substituents selected from W, or R12-R16 is optionally taken together as (CH2)4, (CH2)5 or (CH2)2O(CH2)2, each ring optionally substituted with 1 to 2 CH3; R13 is F, C1-c20 alkyl, C1-C6 haloalkyl, C2-C8 dialkylamino, piperidenyl, pyrrol-idenyl, morpholinyl, phenyl optionally sub-stituted with 1 to 3 substituents selected from W, or R13 is C1-C20 alkoxy C1-C6 haloalkoxy or C1-C4 alkoxy substituted with cyano, nitro, C1-C4 alkoxy, C4-C8 alkoxyalkoxy, C1-C2 alkylthio, C2-C3 alkoxycarbonyl, C3-C5 dialkylaminocarbonyl or phenyl optionally substituted with 1 to 3 substituents independently selected from W, or R13 is phenoxy optionally substituted with 1 to 3 substituents selected from W; R14 and R15 are independently selected from C1-4 alkyl, C2-C4 haloalkyl, phenyl optionally substituted with 1 to 3 substi-tuents independently selected from W or R14 and R15 is optionally taken together as (CH2)2, (CH2)3 or CH2C(CH3)2CH2; W is halogen, CN, NO2, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio, C1-Cz haloalkylthio, Cl-C2 alkylsulfonyl or C1-C2 haloalkylsulfonyl; m is 1 to 5; n is 1 to 4; t is 0 to 3; q is 0 to 2; p is 1 to 3; a is 0 to 2; V is O or S; X is O or S; Y is O or S; and Z is O or S.