DIHYDROFURAN DERIVATIVES AS INSECTICIDAL COMPOUNDS

• US 20120329769A1
• Filed: 01/31/2011
• Published: 12/27/2012
• Est. Priority Date: 02/22/2010
• Status: Active Grant

• Current Assignee: Syngenta Crop Protection LLC (China National Chemical Corporation)
• Original Assignee: Syngenta Crop Protection LLC (China National Chemical Corporation)
• Inventors: El Qacemi, Myriem, Cassayre, Jerome Yves, Toueg, Julie Clementine, Renold, Peter, Pitterna, Thomas
• Granted Patent: US 9,714,228 B2
• Time in Patent Office: Days
• US Class Current: 514/189
• CPC Class Codes: C07D 307/28 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 307/52 Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 307/58 One oxygen atom, e.g. butenolide
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 407/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/14 containing three or more hetero rings

Abstract

The present invention relates to compounds of formula (I) wherein Q is Q1 or Q2 P is P1, heterocyclylor heterocyclyl substituted by one to five Z; and wherein A¹, A², A³, A⁴, G¹, Y¹, Z, R¹, R², R³ and R⁴ are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

Claims

1. A compound of formula (I)

2. A compound according to claim 1 wherein A¹ is C—

R⁵, A² is C—

H, A³ is C—

H or nitrogen and A⁴ is C—

H or nitrogen.

3. A compound according to claim 1 wherein G¹ is oxygen.

4. A compound according to claim 1, wherein P is P1 or a heterocycle selected from H1 to H9

5. A compound according to claim 1 wherein R¹ is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-.

6. A compound according to claim 1 wherein R² is C₁-C₈alkyl or C₁-C₈alkyl substituted by one to five R⁶, C₃-C₁₀cycloalkyl or C₃-C₁₀cycloalkyl substituted by one to five R⁷, aryl-C₁-C₄alkylene- or aryl-C₁-C₄alkylene- wherein the aryl moiety is substituted by one to five R⁸, heterocyclyl-C₁-C₄alkylene- or heterocyclyl-C₁-C₄alkylene- wherein the heterocyclyl moiety is substituted by one to five R⁸, aryl or aryl substituted by one to five R⁸, heterocyclyl or heterocyclyl substituted by one to five R⁸, C₁-C₈alkylaminocarbonyl-C₁-C₄ alkylene, C₁-C₈haloalkylaminocarbonyl-C₁-C₄ alkylene, C₃-C₈cycloalkyl-aminocarbonyl-C₁-C₄ alkylene, or group A

7. A compound according to claim 6 wherein R² is C₁-C₈alkyl or C₁-C₈alkyl substituted by one to five R⁶, C₃-C₁₀cycloalkyl or C₃-C₁₀cycloalkyl substituted by one to five R⁷, phenyl-C₁-C₄alkylene- or phenyl-C₁-C₄alkylene- wherein the phenyl moiety is substituted by one to five R⁸, pyridyl-C₁-C₄alkylene- or pyridyl-C₁-C₄alkylene- wherein the pyridyl moiety is substituted by one to four R⁸, oxetanyl or oxetanyl substituted by one to five R⁸, thietanyl-C₁-C₄ alkylene or thietanyl-C₁-C₄ alkylene wherein the thietanyl moiety is substituted by one to five R⁸, oxo-thietanyl-C₁-C₄ alkylene or oxo-thietanyl-C₁-C₄ alkylene wherein the oxo-thietanyl moiety is substituted by one to five R⁸, dioxo-thietanyl-C₁-C₄ alkylene or dioxo-thietanyl-C₁-C₄ alkylene wherein the dioxo-thietanyl moiety is substituted by one to five R⁸, thietanyl or thietanyl substituted by one to five R⁸, oxo-thietanyl or oxo-thietanyl substituted by one to five R⁸, dioxo-thietanyl or dioxo-thietanyl substituted by one to five R⁸, C₁-C₈alkylaminocarbonyl-C₁-C₄ alkylene, C₁-C₈haloalkylaminocarbonyl-C₁-C₄ alkylene, or C₃-C₈cycloalkyl-aminocarbonyl-C₁-C₄ alkylene or group A

8. A compound according to claim 1 wherein R³ is chlorodifluoromethyl or trifluoromethyl.

9. A compound according to claim 1 wherein R⁴ is aryl or aryl substituted by one to five R⁹.

10. A compound according to claim 1, wherein

P is P1;

Q is Q1 or Q2;

A¹ is C—

R⁵, A² is C—

H, A³ is C—

H and A⁴ is C—

H;

G¹ is oxygen;

Y¹ is CH₂;

R¹ is hydrogen;

R² is C₁-C₈alkyl or C₁-C₈alkyl substituted by one to three halogen atoms, C₃-C₁₀cycloalkyl or C₃-C₁₀cycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-C₁-C₄alkylene- or phenyl-C₁-C₄alkylene- wherein the phenyl moiety is substituted by one to five R⁸, pyridyl-C₁-C₄alkylene- or pyridyl-C₁-C₄alkylene- wherein the pyridyl moiety is substituted by one to four R⁸, thietanyl, oxo-thietanyl, dioxo-thietanyl, C₁-C₄alkylaminocarbonyl-C₁-C₄ alkylene, C₁-C₄haloalkylaminocarbonyl-C₁-C₄ alkylene, C₃-C₆cycloalkyl-aminocarbonyl-C₁-C₄ alkylene, or group A

11. A compound of formula (II)

12. A method of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in claim 1.

13. An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in claim 1.

14. An insecticidal, acaricidal, nematicidal or molluscicidal composition according to claim 13 comprising at least one additional compound having biological activity.

15. A combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B, wherein component A is a compound of formula (I) as defined in claim 1, and compound B is imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide.