Substituted benzoylphenylureas compounds useful as pesticides

• US 4,847,258 A
• Filed: 08/17/1987
• Issued: 07/11/1989
• Est. Priority Date: 08/26/1986
• Status: Expired due to Term

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Kristiansen, Odd, Lang, Robert W., Sturm, Elmar
• Primary Examiner(s): Schwartz, Richard A.
• Assistant Examiner(s): Northington, Zinna
• Application Number:
  US07/086,339
• Time in Patent Office: 694 Days
• Field of Search: 544/316, 514/274
• US Class Current: 514/274
• CPC Class Codes: A01N 47/34 containing the groups , e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
• CPC Class Codes: C07D 239/34 One oxygen atom

Abstract

The invention relates to novel N-benzoyl-N,-4-(5-phenylpyrimid-2-yloxy)phenylureas of formula ##STR1## wherein X₁ is hydrogen, halogen, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio,

X₂ is halogen, methyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio,

Y₁, Y₂, Y₃ and Y₄ are each independently hydrogen, halogen, methyl, trifluoromethyl or methoxy,

Z is methyl, halomethyl containing 1 to 3 halogen atoms or pentafluoroethyl; and

R₁, R₂ and R₃ are each independently hydrogen, halogen, C₁ -C₃ alkyl, trifluoromethyl or C₁ -C₃ alkoxy,

to the preparation thereof and to intermediates for the synthesis of these compounds, as well as to compositions containing them for use in pest control, especially for controlling representatives of the order Acarina that attack plants and animals and for controlling insects. The novel compounds exhibit especially pronounced activity against plant-destructive mites.

Claims

1. A compound of formula I ##STR23## wherein X₁ is hydrogen, halogen, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio,

X₂ is halogen, methyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio,

Y₁, Y₂, Y₃ and Y₄ are each independently hydrogen, halogen, methyl, trifluoromethyl or methoxy,

Z is methyl, halomethyl containing 1 to 3 halogen atoms or pentafluoroethyl;

and

R₁, R₂ and R₃ are each independently hydrogen, halogen, C₁ -C₃ alkyl, trifluoromethyl or C₁ -C₃ alkoxy.

2. A compound of formula I according to claim 1, wherein

X₁ is hydrogen, halogen, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio,

X₂ is halogen, methyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio,

Y₁, Y₂, Y₃ and Y₄ are each independently hydrogen, halogen, methyl, trifluoromethyl or methoxy,

Z is methyl or halomethyl containing 1 to 3 halogen atoms;

and

R₁, R₂ and R₃ are each independently hydrogen, halogen, C₁ -C₃ alkyl, trifluoromethyl or C₁ -C₃ alkoxy.

3. A compound of formula I according to claim 1, wherein

X₁ is hydrogen, halogen or methoxy,

X₂ is halogen or methoxy,

Y₁ and Y₄ are hydrogen,

Y₂ and Y₃ are each independently of the other hydrogen, fluorine, chlorine, methyl or trifluoromethyl,

Z is methyl, dichloromethyl, trichloromethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or pentafluoroethyl;

and

R₁, R₂ and R₃ are each independently hydrogen, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, methoxy or ethoxy.

4. A compound of formula I according to claim 1, wherein X₁ is fluorine, chlorine or methoxy, and X₂ is fluorine or chlorine.

5. A compound of formula I according to claim 1, wherein Y₁ is methyl and Y₂, Y₃ and Y₄ are hydrogen.

6. A compound of formula I according to claim 1, wherein Y₁ and Y₄ are hydrogen, and Y₂ and Y₃ are hydrogen, fluorine or chlorine.

7. A compound of formula I according to claim 1, wherein Z is trifluoromethyl, difluorochloromethyl or pentafluoroethyl.

8. A compound of formula I according to claim 1, wherein R₁ is hydrogen, R₂ is hydrogen, 2-fluoro or 2-chloro, and R₃ is hydrogen, 4-fluoro or 4-chloro.

9. A compound according to claim 1, wherein X₁ and X₂ are fluorine.

10. A compound of formula I according to claim 1, wherein R₁, R₂ and R₃ are hydrogen.

11. A compound according to claim 7 of formula ##STR24##

12. A compound according to claim 7 of formula ##STR25##

13. A compound according to claim 7 of formula ##STR26##

14. A compound according to claim 7 of formula ##STR27##

15. A pesticidal composition which comprises as active ingredient, a pesticidally effective amount of a compound according to claim 1, together with a suitable carrier or other adjuvant.

16. A method of controlling pests selected from insects and representatives of the order Acarina, which method comprises contacting or treating said pests, their various development stages or the locus thereof with a pesticidally effective amount of a compound of formula I according to claim 1.

17. A method according to claim 16 for controlling plant-destructive acarids.

20. A method of controlling pests selected from insects and representatives of the order Acarina, which method comprises contacting or treating said pests, their various development stages or the locus thereof with a pesticidally effective amount of a composition according to claim 15.

18. A compound of formula II, ##STR28## wherein Y₁, Y₂, Y₃ and Y₄ are each independently hydrogen, halogen, methyl, trifluoromethyl or methoxy,

Z is methyl, halomethyl containing 1 to 3 halogen atoms or pentafluoroethyl;

and

R₁, R₂ and R₃ are each independently hydrogen, halogen, C₁ -C₃ alkyl, trifluoromethyl or C₁ -C₃ alkoxy.

19. A compound of formula IV, ##STR29## wherein Y₁, Y₂, Y₃ and Y₄ are each independently hydrogen, halogen, methyl, trifluoromethyl or methoxy,

Z is methyl, halomethyl containing 1 to 3 halogen atoms or pentafluoroethyl;

and

R₁, R₂ and R₃ are each independently hydrogen, halogen, C₁ -C₃ alkyl, trifluoromethyl or C₁ -C₃ alkoxy.