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1. WO2011003796 - PYRIDAZINE COMPOUNDS FOR CONTROLLING INVERTEBRATE PESTS

Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

[ EN ]

Claims:

1. Pyridazine compounds of formulae I or Il


(I) (")

wherein

A is an oxazole or thiazole or imidazole radical of formulae A1 , A2 or A3,


A1 A2 A3

wherein

# denotes the binding site to the remainder of formulae I or II;

Z is O or S for z = 0 or Z is N for z = 1 ;

R41, R42, R43 and R51 are independently of each other selected from hydrogen, halogen, CN, NO2, Ci-Cio-alkyl, C2-Cio-alkenyl and C2-Cio-alkynyl, wherein the 3 last mentioned radicals may be unsubstituted, may be par- tially or fully halogenated or may carry 1 , 2 or 3 identical or different sub- stituents Rx,

or wherein R41, R42, R43 and R51 are further selected from ORa, SRa, C(Y)Rb, C(Y)ORC, S(O)2Rd, NReRf, heterocyclyl, C3-Cio-cycloalkyl,

C5-Cio-cycloalkenyl and phenyl, wherein the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 identical or different sub- stituents Rx;

R52, R53 are selected from hydrogen, halogen, CN, NO2, Ci-Cio-alkyl, C2-Cio-alkenyl and C2-Cio-alkynyl, wherein the 3 last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1 ,

2 or 3 identical or different substituents Rx,

or wherein R52, R53 are further selected from ORa, SRa, C(Y)Rb, C(Y)ORC, S(O)2Rd, NReRf, heterocyclyl, C3-Cio-cycloalkyl,

C5-Cio-cycloalkenyl and phenyl, wherein the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 identical or different sub- stituents Rx, and wherein

R61, R62, R63 are selected from hydrogen, CN, NO2, Ci-Cio-alkyl,

C2-Cio-alkenyl and C2-Cio-alkynyl, wherein the three last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1 , 2 or 3 identical or different substituents Rx,

or wherein R61, R62, R63 are further selected from ORa, SRa, C(Y)Rb, C(Y)ORC, S(O)2Rd, NReRf, C(Y)NRsRh, s(O)mNReRf, C(Y)NR'NReRf, heterocyclyl, C3-Cio-cycloalkyl, Cs-do-cycloalkenyl and phenyl, wherein the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 identical or different substituents Ry;

V is C(RV) or N;

W is C(RW) or N;

with the proviso that either V or W is N;

R1, Ru, Rv and Rw are independently of each other selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy, Ci-C3-haloalkoxy,

Ci-C4-alkylthio, Ci-C3-haloalkylthio, Ci-C4-alkylsulfinyl,

Ci-C3-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C3-haloalkylsulfonyl, C3-C6-cycloalkyl, Cs-Cβ-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl or Ci-C4-alkoxy-Ci-C4-alkyl;

X1 is S, O or NR1a, wherein

R1a is selected from hydrogen, Ci-Cio-alkyl, Ci-C4-haloalkyl, C3-C10- cycloalkyl, Cs-Cio-cycloalkylmethyl, C3-Cio-halocycloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, Ci-Cio-alkoxy-Ci-C4-alkyl, ORa, phenyl, hetaryl, phenyl-Ci-C4-alkyl and hetaryl-Ci-C4-alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry

1 , 2, 3, 4 or substituents which, independently of each other, are selected from halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

X2 is OR2a, NR2bR2c, S(O)mR2d, wherein

R2a is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl,

C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, hetaryl, phenyl-Ci-C4-alkyl and hetaryl-Ci-C4-alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or substituents which, independently of each other, are selected from halogen, cyano, nitro,

Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, and wherein

R2b, R2c are independently of each other selected from hydrogen,

Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylcarbonyl, d-CU-haloalkylcarbonyl, Ci-C4-alkylsulfonyl,

Ci-C4-haloalkylsulfonyl, phenyl, phenylcarbonyl, phenylsulfonyl, hetaryl, hetarylcarbonyl, hetarylsulfonyl, phenyl-Ci-C4-alkyl and hetaryl-Ci-C4-alkyl, wherein the aromatic ring in the eight last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents which, independently of each other, are selected from halogen, cyano, nitro, Ci-C4-alkyl,

Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or

R2b and R2c together with the nitrogen atom to which they are bound form a 5- or 6-membered, saturated or unsaturated heterocycle, which may carry a further heteroatom being selected from O, S and N as a ring member atom and wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents which, independently of each other, are selected from halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and

Ci-C4-haloalkoxy, and wherein

R2d is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl,

C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl,

Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, hetaryl, phenyl-Ci-C4-alkyl and hetaryl-Ci-C4-alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents which, independently of each other, are selected from halogen, cyano, nitro,

Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

is hydrogen, CN, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C3-Cio-cycloalkyl,

C3-Cio-halocycloalkyl, C3-Cio-cycloalkylmethyl, C3-Cio-halocycloalkylmethyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C3-Cio-haloalkynyl, Ci-C4-alkylen-CN, ORa, Ci-C4-alkylen-ORa, C(Y)Rb, Ci-C4-alkylen-C(Y)Rb,

C(Y)ORC, Ci-C4-alkylen-C(Y)ORc, S(O)2Rd, NReRf, Ci-C4-alkylen-NReRf,

C(Y)NRsRh, Ci-C4-alkylen-C(Y)NR9Rh, S(O)mNReRf, C(Y)NR'NReRf, phenyl, hetaryl, phenyl-Ci-C4-alkyl and hetaryl-Ci-C4-alkyl wherein the aromatic ring of the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 identical or different substituents Rx;

m is 0, 1 , or 2;

Y is O or S;

Ra, Rb, Rc are independently of each other selected from hydrogen, Ci-C4-alkyl,

Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl, Cs-Cβ-cycloalkylmethyl,

C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, hetaryl, phenyl-Ci-C4-alkyl and hetaryl- Ci-C4-alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or substituents which, independently of each other, are selected from halogen, cyano, nitro,

Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

Rd is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl,

C3-C6-cycloalkylmethyl, Cs-Cβ-halocycloalkyl, C2-C4-alkenyl,

C2-C4-haloalkenyl, C2-C4-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, hetaryl, phenyl-Ci-C4-alkyl and hetaryl-Ci-C4-alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents which are independently of each other selected from halo- gen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and

Ci-C4-haloalkoxy;

Re, Rf are independently of each other selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl, Cs-Cβ-cycloalkylmethyl,

C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl,

Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, phenyl, phenylcarbonyl, phen- ylsulfonyl, hetaryl, hetarylcarbonyl, hetarylsulfonyl, phenyl-Ci-C4-alkyl and hetaryl-Ci-C4-alkyl, wherein the aromatic ring in the eight last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents which, independently of each other, are selected from halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or

Re and Rf together with the nitrogen atom to which they are bound form a 5- or 6-membered, saturated or unsaturated heterocycle, which may carry a further heteroatom being selected from O, S and N as a ring member atom

and wherein the heterocycle may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents which are independently of each other selected from halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and

Ci-C4-haloalkoxy;

R9, Rh are independently of each other selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, hetaryl, phenyl-Ci-C4-alkyl and hetaryl-Ci-C4-alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or substituents which are independently of each other selected from halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy;

R1 is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl,

C3-C6-cycloalkylmethyl, Cs-Cβ-halocycloalkyl, C2-C4-alkenyl,

C2-C4-haloalkenyl, C2-C4-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenyl-Ci-C4-alkyl wherein the phenyl ring in the two last mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents which are independently of each other selected from halogen, cyano, nitro,

Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

Rx are independently of each other selected from cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, d-Cio-alkylcarbonyl, Cs-Cβ-cycloalkyl, 5- to 7-membered heterocyclyl, phenyl, Cs-Cβ-cycloalkoxy, 3- to 6-membered heterocyclyloxy and phenoxy, wherein the last 6 mentioned radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 radicals Ry; and wherein

Ry is selected from halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl,

Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl,

Ci-C4-haloalkylsulfonyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, C3-C6-cycloalkyl, Cs-Cβ-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl,

C2-C4-alkynyl and Ci-C4-alkoxy-Ci-C4-alkyl;

or their agriculturally or veterinally acceptable salts, N-oxides, enantiomers or di- astereomers thereof.

2. The compounds as claimed in claim 1 , wherein the pyridazine compound is a compound of formula I.

3. The compounds as claimed in claim 1 or 2, wherein X1 is oxygen.

4. The compounds as claimed in any of the claims 1 to 3, wherein R1 is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-C4-alkylene-CN, heterocyclyl-d-Cs-alkyl, hetaryl-C-i-Cs-alkyl, Ci-C5-alkylen-ORa or C3-Cio-cycloalkyl-Ci-C5-alkyl..

5. The compounds as claimed in any of the claims 1 to 4, wherein R1 is hydrogen or C-i-Cs-alkyl.

6. The compounds as claimed in any of the claims 1 to 5, wherein R1, Ru and Rw, are selected independently of each other from hydrogen, methyl, difluoromethyl, trifluoromethyl, methoxy, difluoromethoxy and trifluoromethoxy.

7. The compounds as claimed in any of the claims 1 to 6, wherein W is CRW with Rw being hydrogen.

8. The compounds as claimed in any of the claims 1 to 7, wherein R1, Ru and Rw are hydrogen.

9. The compounds as claimed in any of the claims 1 to 8 wherein Z is O.

10. The compounds as claimed in any of the claims 1 to 8 wherein Z is S.

1 1. The compounds as claimed in any of the claims 1 to 8 wherein Z is N.

12. The compounds as claimed in any of the claims 1 to 1 1 , wherein A is a radical A1.

13. The compounds as claimed in claim 12, wherein R41 is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl and Cs-Cβ-halocycloalkyl.

14. The compounds as claimed in any of the claims 12 to 13 , wherein R51 is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl and C3-C6- halocycloalkyl.

15. The compounds as claimed in any of the claims 12 to 14, wherein R61 is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl- Ci-C4-alkyl, hetero- cyclyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkyl-CN.

16. The compounds as claimed in any of claims 1 to 11 , wherein A is a radical A2.

17. The compounds as claimed in claim 16, wherein R42 is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl and Cs-Cβ-halocycloalkyl.

18. The compounds as claimed in any of the claims 16 to 17, wherein R52 is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl and C3-C6- halocycloalkyl.

19. The compounds as claimed in any of the claims 16 to 18, wherein R62 is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, hetero- cyclyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkyl-CN.

20. The compounds as claimed in any of the claims 1 to 1 1 , wherein A is a radical A3.

21. The compounds as claimed in claim 20, wherein R43 is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl and Cs-Cβ-halocycloalkyl.

22. The compounds as claimed in any of the claims 20 to 21 , wherein R53 is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cβ-cycloalkyl and C3-C6- halocycloalkyl.

23. The compounds as claimed in any of the claims 20 to 22, wherein R63 is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, hetero- cyclyl- Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkyl-CN.

24. A method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, seed, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a pyridazine compound of formulae I or 11 or a salt or an N-oxide thereof as defined in any of the claims 1 to 23.

25. The method as claimed in claim 24, wherein the invertebrate pests are arthropod pests and/or nematodes.

26. The method as claimed in claim 25, wherein the invertebrate pests are insects.

27. The method as claimed in claim 26, wherein the invertebrate pests are insects of the order Homoptera.

28. A method for protecting plant propagation material and/or the plants which grow therefrom, which method comprises treating the plant propagation material with a pesticidally effective amount of a compound of the formulae I or Il or an agriculturally acceptable salt or an N-oxide thereof as defined in any of the claims 1 to 23.

29. Plant propagation material, comprising at least one compound of formulae I or Il as defined in any of the claims 1 to 23 and/or an agriculturally acceptable salt or an N-oxide thereof.