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United States Patent 19 11 Patent Number: 5,380,718 Harrison Et Al

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United States Patent 19 11 Patent Number: 5,380,718 Harrison Et Al USOO538078A United States Patent 19 11 Patent Number: 5,380,718 Harrison et al. 45 Date of Patent: Jan. 10, 1995 54 ARTHROPODICIDAL FUSED TETRAHYDROPYRDAZINES FOREIGN PATENT DOCUMENTS 153127B1 8/1985 European Pat. Off.. 75 Inventors: Charles R. Harrison, Newark; George 322168 6/1989 European Pat. Off.. P. Lahm; Thomas M. Stevenson, both WO88/05046 7/1988 WIPO. of Wilmington, all of Del. WO88/O7994 10/1988 WIPO . 73 Assignee: E. I. Du Pont de Nemours and WO89/00562 1/1989 WIPO . Company, Wilmington, Del. WO90/03378 4/1990 WIPO . OTHER PUBLICATIONS 21) Appl. No.: 945,965 Hagiwara et al, Chemical Abstractsl , vol. 115, No. 22 PCT Filed: Apr. 30, 1991 208008 (1991) (Abstract of JP 03161478, Jul 11, 1991). W. R. Vaughan, J. Org. Chem. 20:1619-1626 (1955). 86 PCT No.: PCT/US91/02836 H. M. Hassaneen et al., J. Heterocyclic Chem. S 371 Date: Nov. 12, 1992 21:1013-1016 (Jul.-Aug. 1984). Shabarov et al Chem. Abstracts, 68(19):86912n (1968). S 102(e) Date: Nov. 12, 1992 Levina et al Chem. Abstracts 54:19544f (1960). 87 PCT Pub. No.: WO91/17983 Rudenro Chem. Abstraacts, 55:25808g (1961). Shabarov et al. Chem. Abstracts, 55:12418f (1961). PCT Pub. Date: Nov. 28, 1991 T. Shimizu, J. Org. Chem. 52:2277 (1987). T. Shimizu, Chem. Soc. Jap., 55:2450 (1982). Related U.S. Application Data Tomita et al., J. Het. Chem. 27, pp. 707-710 (1990). 63 Continuation-in-part of Ser. No. 570,103, Aug. 17, Primary Examiner-Emily Bernhardt 1990, abandoned, which is a continuation-in-part of Attorney, Agent, or Firm-James A. Costello Ser. No. 523,697, May 15, 1990, abandoned. 57 ABSTRACT 51) Int. Cl6................ C07D 237/26; CO7D 491/048; CO7D 487/04; CO7D 495/04 Arthropodicidal tetrahydropyridazines of Formulae I 52 U.S.C. ........................................ 514/80; 514/81; and II, 514/85; 514/224.5; 514/230.2; 514/232.8; 514/233.2; 514/247; 514/248; 514/252; 544/34; X 544/95; 544/101; 544/115; 544/229; 544/232; 544/233; 544/234,544/238; 544/239; 544/240; o-c--G 544/241; 560/51; 562/405; 562/462; 568/326; Y 568/327 58 Field of Search ............... 544/233,232, 234, 229, X1 I 544/115, 34, 95, 101; 514/80, 81, 248, 232.8, Q-c-N-G 233.2, 224.5, 230.2 wherein QX,XY, and G are as defined in the text, 56 References Cited compositions containing them and their use in the con U.S. PATENT DOCUMENTS trol of arthropods. 4,070,365 1/1978 van Daalen et al. ............... 548/379 4,602,019 7/1986 Sircar et al. ......................... 514/248 11 Claims, No Drawings 5,380,718 1. 2 AR OPODCDAL FUSED where R/Ar are C6H5/C6Hs; CO2C2H5/C6Hs; C(O)NHC6H5/C6Hs; CH=CHC6H5/C6H5; and TETRAHYDROPYRIDAZINES CH3/4-NO2-C6H4. CROSS-REFERENCE TO RELATED 5 J. Org. Chenn., 1987, 52, 2277 discloses pyrazolidines APPLICATIONS as does Chem. Soc. Jap, 55, 2450 (1982). This is a continuation-in-part of application bearing EPA 330,678 EPA 322,168, WO 88/07994, WO U.S. Ser. No. 07/570,103 filed on 17 Aug. 1990, now 88/05046, WO 89/00562 and WO 90/03378 disclose abandoned, which is a continuation-in-part of applica O insecticidal pyrazolines. tion bearing U.S. Ser. No. 07/523,697 filed on 15 May SUMMARY OF THE INVENTION 1990, now abandoned. The invention pertains to compounds of Formulae I BACKGROUND OF THE INVENTION and II, including all geometric and stereoisomers, agri 1. Field of the Invention 15 culturally suitable salts thereof, agricultural composi Insecticidal tetrahydropyridazines, compositions tions containing them and their use for the control of containing them and methods for controlling arthro arthropods in both agronomic and nonagronomic uses. pods employing them. The compounds are: 2. State of the Art 20 Vaughan, J. Org. Chem..., 20 (1955), pages 1619 to 1626, discloses 1,5-diphenyl-2-pyrazoline-3-carboxa mide. U.S. Pat. No. 4,070,365 discloses insecticidal com pounds of the formula: 25 X1 I 30 wherein: Q is selected from the group / N Q-1 o'-O-N 35 wherein X is halogen; and Y is halogen, NO2 or alkyl. ' EP 153,127 discloses insecticidal compounds of the formula: Z A. Q-2 A Z 45 ENR'R4 c-1 , N R5 M \ (R2) N R6, N CH2 S. R7 U1NN-B 50 h Q-3 wherein A is unsubstituted or substituted phenyl; B is unsubstituted or substituted phenyl; U is O, S or NR; 55 and R, Y and Z are broadly defined. Harihash et al., J. Heterocyclic Chem, 21 (1984), at page 1013, discloses the preparation of pyrazoline com pounds: 60 Z A Q-4 R H E R3 R8 y N NN ch: 65 (R) N Sa R9, Ar O 5,380,718 5 6 loalkoxy, Si(R32)(R33)R31, N(R26)R27, NO2, OC R18 and R19 can be taken together as (OR29 and J; -CH2CH2CH2CH2CH2- or -CH2CH2OCH2C J is selected from the group consisting of saturated, H2-: partially saturated or aromatic 5- or 6-membered R20 is selected from the group C1-C6 alkyl, C1-C6 heterocyclic rings, bonded through carbon or ni haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, trogen, containing 1-4 heteroatoms independently C2-C6 alkynyl, C3-C6 haloalkynyl, C2-C6 alkoxyal selected from the group consisting of 0-2 oxygen, kyl, C2-C6 alkylthioalkyl, C1-C6 nitroalkyl, C2-C6 0-2 sulfur and 0-4 nitrogen; said J value optionally cyanoalkyl, C3-C8 alkoxycarbonylalkyl, C3-C6 containing one carbonyl and optionally substituted cycloalkyl, C3-C6 halocycloalkyl, phenyl option by one or more groups selected from W: 10 ally substituted with 1 to 3 substituents indepen R is selected from the group H, halogen, C1-C6 dently selected from W, benzyl optionally substi alkyl, CO2R, phenyl, pyridinyl and phenyl or tuted with 1 to 3 substituents independently se pyridinyl substituted with Cl, Br, F, CF3, NO2, lected from W, halogen CN, N3, SCN, NO2, OR21, OCF3, OCF2H or CN; SR21, S(O)R21, S(O)2R21, OCOR21, OSO)2R21, Rand R7 are independently selected from the group 15 COR21, COR21, C(O)NR21R22, SO2NR21R22, H and C1-C2 alkyl; NR21R22, NR22COR21, OC(O)NHR21, R is selected from the group H, C1-C6 alkyl, NR22C(O)NHR21 and NR22SOR212; or when m, CO2R2, and optionally substituted phenyl and in or p is 2, (R)2 when attached to adjacent atoms pyridinyl, wherein the substituents are selected can be taken together, or (R2)2 when attached to from Cl, Br, F, CF3, NO2, OCF3, OCF2H or CN; 20 adjacent atoms can be taken together, or (R20)2 R and Rs can be taken together to form =O; when attached to adjacent atoms can be taken to R6 and R7 can be taken together to form =O; gether as -OCH2O-, -OCF2O-, -OCH2C R8 is selected from the group H and C1-C2 alkyl; H2O-, -CH2C(CH3)2O-, -CF2CFO- or R9 is selected from the group H, C1-C2 alkyl and -OCF2CF2O- to form a cyclic bridge; provided C1-C2 alkylcarbonyl; that when R, R2 or R20 is S(O)R21, S(O)2R21, R10 is selected from the group H, C1-C4 alkyl, C1-C4 OC(O)R21 or OS(O)2R21 then R21 is other than H; haloalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkyl R21 is selected from the group H, C1-C6 alkyl, C1-C6 carbonyl, C2-C4 alkoxycarbonyl C2-C4 haloalkox haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, ycarbonyl, C2-C5 alkylaminocarbonyl, C3-C6 cy C2-C6 alkynyl, C3-C6 haloalkynyl, C2-C6alkoxyal cloalkyl, C3-C6 halocycloalkyl, C4-C7 alkylcy 30 kyl, C2-C6 alkylthioalkyl, C1-C6 nitroalkyl, C2-C6 cloalkyl, C4-C7 haloalkylcycloalkyl, C1-C4 alkyl cyanoalkyl, C3-C8 alkoxycarbonylalkyl, C3-C6 sulfonyl, C1-C4 haloalkylsulfonyl and SO2Ph op cycloalkyl, C3-C6 halocycloalkyl, and optionally tionally substituted with Cl, Br or CH3; substituted phenyland benzyl wherein the substitu R11 is selected from the group H, C1-C4 alkyl, C1-C4 35 ents are 1 to 3 substituents independently selected haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, SR21, from W: S(OR21, S(O)2R21, COR21, CO2R21, R22 is selected from the group H and C1-C4 alkyl; or C(O)NR21R25, C(S)NR21R25, C(S)R21, C(S)OR21, R21 and R22 when attached to the same atom can be P(O)(OR21)2, P(S)(OR21)2, P(O)(R21)OR21, taken together as -(CH2)4-, -(CH2)5-, or P(O)(R2)SR25, and optionally substituted phenyl -CH2CH2OCH2CH2-; and benzyl wherein the substituents(s) are selected R23 is selected from the group H, C1-C4 alkyl, C2-C4 from F, Cl, Br, CH3, CF3 or OCF3; provided that alkenyl, C2-C4 alkynyl, C2-C4 alkylcarbonyl, when R11 is other than C(O)R21, C(O)NR21R25 or C2-C4 alkoxycarbonyl and C1-C4 alkylsulfonyl; C(S)NR21R25then R21 is other than H: R24 is C1-C3 alkyl; R2 is selected from the group C1-C3 alkyl, benzyl 45 R25 is selected from the group H, C1-C4 alkyl, C2-C4 optionally substituted with R1, C2-C4 alkenyl, alkenyl and C2-C4 alkynyl; C2-C4 alkynyl, C1-C3 haloalkyl, C2-C4 haloalke R26 is selected from the group H, C(O)C1-C6 alkyl, nyl, C3-C6 cycloalkyl and C1-C3 alkyl substituted CO2C1-C6 alkyl, optionally substituted C1-C4 al with OCH3, OCH2CH3, NO2, CN, CO2CH3, kyl, optionally substituted C2-C4 alkenyl, and op CO2CH2CH3, SCH3 or SCH2CH3; 50 tionally substituted C2-C4 alkynyl, the substituents R13 is selected from the group H, C1-C4 alkyl C1-C4 selected from C1-C2 alkoxy, CN, C(O)R3 and haloalkyl, C2-C4 alkoxycarbonyl, and optionally CO2R31; substituted phenyl and pyridinyl wherein the sub R27 is selected from the group H, C1-C3 alkyl, phenyl, stituents(s) are selected from R15; or phenyl substituted with W, benzyl and benzyl sub R12 and R13 can be taken together to form -(CH2 55 stituted with W: )4-, -(CH2)5- or -CH2CH2OCH2CH2- each R28 is selected from the group H, C1-C4 alkyl, C2-C4 of which is optionally substituted with 1 or 2 CH3 alkenyl and C2-C4 alkynyl; groups; R29 and R30 are independently selected from the R1 is selected from the group H and C1-C4 alkyl; or group H and C1-C2 alkyl; R13 and R14 can be taken together to form -(CH2 60 R3 is selected from the group C1-C3 alkyl, phenyl )4-, -(CH2)5- or CH2CH2OCH2CH2 each of and phenyl substituted with W; which is
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