TH45985A - Tetrachin derivatives that are effective in killing insects. - Google Patents

Abstract

DC60 (08/08/43) Inventions concerning compounds of general formula (chemical formula) (I), where T-V is -N=N- or -NH-NH-;X1 is R1; X2 and X3 each independent of each other is H or R1; R1 is, for example, halogen, CN,NO2, C1-C6-alkyl, C3-C8 cycloalkyl, C1-C6 halogen, C3-C8 halocycloalkyl, C1-C6 alkoxy, C3-C8 cycloalkoxy or C1-C6 halogenkoxy. AR1 is an unsubstituted or substituted aryl or heteroaryl of one to four groups. AR2 is an unsubstituted or substituted aryl or heteroaryl. One to five groups A are single bonds, C1-C12 alkylene, O, O(C1-C12 alkylene), S(O)n, S(O)n(C1-C12 alkylene), C2-C8 alkiniline, C2-C8 alkyneline; NR6, NR6(C1-C12 alkylene) or C(=Z); Z is O, NR4, NNR4R5 or NOR4; R2 is H, C1-C6 alkyl or C3-C8 cycloalkyl; and each independent group of R4 and R5 is H, C1-C6 alkyl or C1-C6 haloalkyl. R6 is H, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C2-C8 alkynyl, C2-C8 alkynyl, aryl-C1-C6 alkyl, (CH2)pC(O)R7 or C1-C6 alkoxy-C2-C6 alkyl; R7 is H, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, N(R8)2 or C1-C6 alkoxy-C2-C6 alkyl; R8 is H, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl or aryl-C1-C6 alkyl; n is 0, 1, or 2; p is 0, 1, 2, 3, 4, 5, or 6; and Q is O or S; the methods for preparing those compounds and their uses; insecticides, the active ingredient selected from those compounds; and the methods for preparing those mixtures and their uses; intermediates in the preparation of those compounds; and the methods for preparing those intermediates and their uses. The invention of a compound of a general formula (chemical formula) (I), where T-V is -N=N- or -NH-NH-;X1 is R1; X2 and X3 each independent of the other are H or R1; R1 is, for example, a halogen, CN, NO2, C1-C6-alkyl, C3-C8 cycloalkyl, C1-C6 halogen, C3-C8 halocycloalkyl, C1-C6 alkoxy, C3-C8 cycloalkoxy or C1-C6 halogenkoxy. AR1 is an unsubstituted or substituted aryl or heteroaryl of one to four groups. AR2 is an unsubstituted or substituted aryl or heteroaryl. One to five groups A are single bonds, C1-C12 alkylene, O, O(C1-C12 alkylene), S(O)n, S(O)n(C1-C12 alkylene), C2-C8 alkiniline, C2-C8 alkyneline; NR6, NR6(C1-C12 alkylene) or C(=Z); Z is O, NR4, NNR4R5 or NOR4; R2 is H, C1-C6 alkyl or C3-C8 cycloalkyl; and each independent group of R4 and R5 is H, C1-C6 alkyl or C1-C6 haloalkyl. R6 is H, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C2-C8 alkynyl, C2-C8 alkynyl, aryl-C1-C6 alkyl, (CH2)pC(O)R7 or C1-C6 alkoxy-C2-C6 alkyl; R7 is H, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, N(R8)2 or C1-C6 alkoxy-C2-C6 alkyl; R8 is H, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl or aryl-C1-C6 alkyl; n is 0, 1, or 2; p is 0, 1, 2, 3, 4, 5, or 6; and Q is O or S; the methods for preparing those compounds and their uses; insecticides, the active ingredient selected from those compounds; and the methods for preparing those mixtures and their uses; intermediates in the preparation of those compounds; and the methods for preparing those intermediates and their uses.

Claims (10)

1. Compounds of the formula (chemical formula) (I), where T-V is -N=N- or -NH-NH-; X1 is R1; X2 and X3 each independent of each other is H or R1; R1 is a halogen, CN, NO2, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-haloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C3-C8-cycloalkoxy, C1-C6-haloalkoxy, C3-C8-halocycloalkoxy, C1-C6-alkylthio, C3-C8-cycloalkylthio, C1-C6-haloalkylthio, C3-C8-halocycloalkylthio; Ar1 is an aryl or heteroaryl, either unsubstituted or substituted by one to four selectable substituents. From groups containing OH, halogen, CN, NO2, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6 alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 halocycloalkyl, C1-C6 alkoxicyl, C3-C8-cycloalkoxy, C1-C6 haloalkoxy, C3-C8 halocycloalkoxy, C1-C6 alkylthio, C3-C8-cycloalkylthio, C1-C6 haloalkylthio, C3-C8 halocycloalkylthio, C1-C6 alkylsulfinyl, C3-C8-cycloalkylsulfinyl. C1-C6 haloalkylsulfinils, C3-C8 halocycloalkylsulfinils, C1-C6 alkylsulfonils, C3-C8 cycloalkylsulfonils, C1-C6 haloalkylsulfonils, C3-C8 halocycloalkylsulfonils, C2-C8 alkylnils, C2-C8 alkynils, C1-C6 alkylcarbonyls, C1-C6 alkyl-C(=NOR2) and R3; AR2 are unsubstituted or substituted aryls or heteroaryls of one to five groups, which are selected. Substituting from groups containing OH, halogens, CN, NO2, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 alkyl-C3-C8 cycloalkyl, C3-C8 cycloalkyl-, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 halocycloalkyl, C1-C6 alkylthio, C3-C8 cycloalkoxy, C1-C6 haloalkoxy, C3-C8 halocycloalkoxy, C1-C6 alkylthio, C3-C8 cycloalkylthio, C1-C6 haloalkylthio, C3-C8 halocycloalkylthio, C1-C6 alkylsulfinyl, C3-C8-cycloalkylsulfinyl. C1-C6 halo alkylsulfinyl, C3-C8 halocycloalkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 halocycloalkylsulfonyl, C2-C8 alkylnyl, C2-C8 alkyneyl, C1-C6 alkylcarbonyl, C1-C6 alkyl-C(=NOR2) and R3; A is a single bond, C1-C12 alkyneylene, O, O(C1-C12 alkyneylene), S(O)n, S(O)n(C1-C12 alkyneylene), C2-C8 alkyneylene, C2-C8 alkyneylene; NR6, NR6(C1-C12 alkyl) or C(=Z): Z is O, NR4, NNR4R5 or NOR4; R2 is H, C1-C6 alkyl or C3-C8 cycloalkyl; R3 is (chemical formula); each independent group of R4 and R5 is H, C1-C6 alkyl or C1-C6 haloalkyl; R6 is H, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C2-C8 alkynyl, C2-C8 alkynyl, aryl-C1-C6 alkyl, (CH2)pC(O)R7 or C1-C6 alkoxy-C2-C6 alkyl; R7 is H, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6-alkoxy, N(R8)2 or C1-C alkoxy-C2-C6 alkyl; R8 is H, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl or aryl-C1-C6 alkyl; R9 and R10 each independent of the other is H or C1-C6 alkyl: m is 1, 2, 3 or 4; n is 0, 1 or 2; p is 0, 1, 2, 3, 4, 5 or 6; and Q is O or S; provided that T-V is -NH-NH-, X1 is a halogen, X2 and X3 are both hydrogen, Ar1 and Ar2 are both phenyl. Which may be irreplaceable or substituted; A is not a single bond; or that applies possible E/Z isomers, mixtures of E/Z isomers and/or totomers of those isomers, in each case in free form or in the form of salts. 2. The compound according to claim 1 of formula (I) in its free form. 3. The compound according to claim 1 or 2 of formula (I) where X3 is H. 4. Any one of the claims 1 through 3 of formula (I) in which Ar2 is an aryl or heteroaryl that is not substituted or has one or three substituted substituents chosen from Groups containing OH, halogens, CN, NO2, C1-C4-alkyl, C3-C6 cycloalkyl, C1-C4 alkyl-C3-C4 cycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, C3-C4 haloalkyl, C3-C6 halocycloalkyl, C1-C4 alkoxy, C3-C6 cycloalkoxy, C1-C4 haloalkoxy, C3-C6 halocycloalkoxy, C1-C4 alkylthio, C3-C6 cycloalkylthio, C1-C4 haloalkylthio, C3-C6 halocycloalkylthio, C1-C4 alkylsulfinyl, C3-C6-cycloalkylsulfinyl. C1-C4 haloalkylsulfinyl, C3-C6 halocycloalkylsulfinyl, C1-4 alkylsulfonyl, C3-C6 cycloalkylsulfonyl, C1-C4 haloalkylsulfonyl, C3-C6 halocycloalkylsulfonyl, C2-C6 alkynyl, C2-C6 alkynyl, C1-C4 alkylcarbonyl, C1-C4 alkyl-C(=NOR2) and R3. 5. Any of the compounds under claims 1 through 4 of formula (I), where A is -CH2-, -O- CH2-, C2-C4alkyniline, C2-C4alkyniline or NR3. 6. Any of the compounds under claims 1 through 5 of formula (I) in which T-V is -N=N- 7. Any of the compounds under claims 1 through 6 of formula (I), where X1 and X2 are halogens and X3 is H. 8. A mixture for the control of insect pests, which contains the components of formulation (I) as described in claim 1 and at least one excipient as the active ingredient. 9. A method of controlling insect pests, which includes the use of at least one of the compounds of Formula (I) as described in Claim 1 in an amount that is effective against the insect pests or at the location where the insect pests are present. 10. Use of the compound of formula (I) as described in claim 1 for the control of insect pests.