METHODS OF CONTROLLING NEONICOTINOID RESISTANT PESTS

• US 20160050930A1
• Filed: 03/12/2014
• Published: 02/25/2016
• Est. Priority Date: 03/28/2013
• Status: Abandoned Application

• Current Assignee: Syngenta Limited (China National Chemical Corporation), Syngenta Participations AG (China National Chemical Corporation)
• Original Assignee: Syngenta Limited (China National Chemical Corporation), Syngenta Participations AG (China National Chemical Corporation)
• Inventors: Benfatti, Fides, Godfrey, Christopher Richard Ayles, Jeanguenat, Andre, Pabba, Jagadish, Rendler, Sebastian, Schaetzer, Jurgen Harry, Slater, Russell, Crossthwaite, Andrew
• Application Number:
  US14/780,575
• Publication Number:
  US 20160050930A1
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: C07D 451/02 containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof

Abstract

The present invention relates to a method of controlling insects (in particular insects of the order Hemiptera, especially aphids and whitefly) that are resistant to neonicotinoid insecticides, to methods of controlling insects whereby undesired insects are affected but beneficial arthropods are not affected, using compounds of formula (I) (where A, R1 and R2 are as defined above), and, further, to novel compounds of formula (I) which are useful in the aforementioned methods and/or which possess enhanced insecticidal properties, and to compositions containing said compounds.

Claims

1. A method of controlling insects from the order hemiptera, which insects are resistant to a neonicotinoid insecticide, which method comprises applying to said neonicotinoid resistant insects a compound of formula (I):

2. A method according to claim 1 wherein A is —

CH═

CH—

.

3. A method according to claim 1 wherein R¹ is F, I, or Br.

4. A method according to claim 1 wherein R² is hydrogen, formyl, C₁-C₆alkyl (optionally substituted by phenyl, heteroaryl (wherein heteroaryl is pyridyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl or thiadiazolyl) or heterocyclyl (wherein heterocyclyl is tetrahydrofuranyl, [1,3]dioxolanyl, oxetanyl, thietanyl, 1-oxo-thietanyl or 1,1-dioxo-thietanyl), which themselves can be optionally substituted by one or two substituents independently selected from halogen, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, and C₁-C₄alkoxy), C₁-C₆haloalkyl (optionally substituted by one or two substituents independently selected from C₁-C₄-alkoxy, tri(C₁-C₄alkyl)silyloxy), and C₃-C₅alkenyl), C₁-C₆cyanoalkyl, C₁-C₆alkoxy(C₁-C₆)alkyl, C₁-C₆alkylcarbonyl(C₁-C₆)alkyl, C₁-C₆alkoxycarbonyl(C₁-C₆)alkyl, C₁-C₄alkylaminocarbonyl(C₁-C₆)alkyl, di(C₁-C₄alkyl)aminocarbonyl(C₁-C₆)alkyl, C₁-C₄haloalkylaminocarbonyl(C₁-C₆)alkyl, C₂-C₆alkenyloxycarbonyl(C₁-C₆)alkyl, C₃-C₆alkynyloxycarbonyl(C₁-C₃)alkyl, C₃-C₆cycloalkyl (optionally substituted by one or two substituents independently selected from C₁-C₄alkyl, and C₁-C₄haloalkyl, and, additionally, one of the ring member units can optionally represent C═

O), C₃-C₆halocycloalkyl, C₄-C₇cycloalkenyl (optionally substituted by one or two substituents independently selected from C₁-C₄alkyl, and C₁-C₄haloalkyl, and, additionally, one of the ring member units can optionally represent C═

O), C₁-C₆alkyl-S(═

O)n¹(C₁-C₆)alkyl where n¹ is 0, 1 or 2, C₃-C₆alkenyl, C₃-C₆haloalkenyl, phenyl(C₃-C₆)alkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, heterocyclyl (wherein heterocyclyl is oxetanyl, 3-tetrahydrofuranyl-2-one, 1,1-dioxo-thietanyl, 1-oxo-thietanyl or thietanyl, and is optionally substituted by one or two substituents independently selected from halogen, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, and C₁-C₄alkoxy, and, additionally, a ring member unit can optionally represent C═

O or C═

NR⁵ where R⁵ is C₁-C₄ alkyl, or C₁-C₄ alkoxy);

or R² represents the group “

—

C(R⁷)(R⁸)(R⁹)”

wherein R⁷ is C₁-C₄alkyl, C₁-C₄haloalkyl, or cyclopropyl;

R⁸ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, or cyclopropyl, preferably hydrogen; and

R⁹ is cyano, C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₁-C₄alkoxy, C₂-C₅alkynyl, C₂-C₄alkoxycarbonyl, C₁-C₄alkylaminocarbonyl, di(C₁-C₃alkyl)aminocarbonyl, C₁-C₂haloalkylaminocarbonyl, C₃-C₆alkenyloxycarbonyl, C₃-C₄alkynyloxycarbonyl, or C₁-C₃alkylcarbonyl.

5. A method according to claim 1 wherein undesired insects from the order Hemiptera which are resistant to one or more of the neonicotinoid insecticides are controlled but beneficial arthropods are not affected.

6. A method according to claim 1 wherein the method comprises applying a compound of formula (I) and one or more beneficial arthropods.

7. A method according to claim 5 wherein the beneficial arthropods are one or more beneficial insects or predatory mites selected from Orius insidiosus, Orius laevigatus, Orius majusculus, Coccinella septempunctata, Adalia bipunctata, Amblydromalus limonicus, Amblyseius andersoni, Amblyseius barkeri, Amblyseius califomicus, Amblyseius cucumeris, Amblyseius montdorensis, Amblyseius swirskii, Phytoseiulus persimilis, Syrphus spp., and Phytoseiulus persimilis.

8. A method according to claim 1 wherein the neonicotinoid resistant insects are from the Aleyrodidae family or the Aphididae family.

9. A compound of formula (IL)

10. A compound of the formula

11. An insecticidal composition comprising an insecticidally effective amount of a compound of formula (IL) as defined in claim 9.