WO2010005692A4

WO2010005692A4 - Insecticidal cyclic carbonyl amidines

Info

Publication number: WO2010005692A4
Application number: PCT/US2009/047321
Authority: WO
Inventors: Wenming Zhang; Stephen Frederick Mccann
Original assignee: E. I. Du Pont De Nemours And Company
Priority date: 2008-06-16
Filing date: 2009-06-15
Publication date: 2010-06-03
Also published as: WO2010005692A3; WO2010005692A2

Abstract

Disclosed are compounds of Formula (I), including all stereoisomers, and salts thereof, wherein Y is O, S, NR⁵ or CR³R⁴, G is a direct bond, and Z is CR³R⁴ or NR⁵; or Y is CR³R⁴, G is a direct bond, and Z is O or S; or Y is O, S, NR⁵or CR³R⁴, G is CR³R⁴, and Z is O, S, NR⁵ or CR³R⁴; or Y is O, and G–Z is CH=CH; or Y–G is CH=CH, and Z is O, S or NR⁵; and R¹, R², R³, R⁴, R⁵ and Q are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention.

Claims

AMENDED CLAIMS received by the International Bureau on 15 April 2010 (15.04.2010)

1. A compound selected from Formula 1 or a salt thereof,

wherein

Y is O, S, NR⁵ or CR³R⁴, G is a direct bond, and Z is CR³R⁴ or NR⁵; or

Y is CR³R⁴, G is a direct bond, and Z is O or S; or

Y is O, S, NR⁵ or CR³R⁴, G is CR³R⁴, and Z is O, S, NR⁵ or CR³R⁴; or

Y is O, and G-Z is CH=CH; or Y-G is CH=CH, and Z is O or S;

R¹ is H, C₁-C₃ alkoxy, C(O)R⁶ or SO₂R⁷; or C₁-C₄ alkyl, C₃-C₄ alkenyl, C₃-C₄ alkynyl, C₃-C₄ cycloalkyl, C₄-C5 cycloalkylalkyl, C₄-C5 alkylcycloalkyl or benzyl, each optionally substituted with 1 to 5 halogen;

R² is H or C₁-C₂ alkyl; each R³ is independently H or CH₃; each R⁴ is independently H or CH₃; each R⁵ is independently H, C₁-C₂ alkyl or C₁-C₂ haloalkyl;

R⁶ is C₁-C₂ alkyl or C₁-C₂ haloalkyl;

R⁷ is C₁-C₂ alkyl or C₁-C₂ haloalkyl; and

Q is a 5- or 6-membered fully unsaturated heterocyclic ring containing as ring members at least one nitrogen atom and other ring members selected from carbon, oxygen and sulfur atoms, said ring optionally substituted with 1 to 3 substituents selected from halogen, cyano, nitro, and C_j-C₄ alkyl, C₁-C₄ alkoxy and C₁-C₃ alkylthio, each optionally substituted with 1 to 5 fluorine or chlorine; or 3-tetrahydrofuranyl; provided that when Y is CR³R⁴, G is a direct bond, Z is S, and R¹, R², R³ and R⁴ are H, then Q is other than 5-methyl-2-pyrazinyl or 2-pyridinyl.

2. A compound of Claim 1 wherein

Y is O, G is a direct bond, and Z is CR³R⁴ or NR⁵; 116

R¹ is H; or C₁-C₃ alkyl or cyclopropyl, each optionally substituted with 1 to 3 halogen;

R² is H; and

Q is a heterocyclic ring selected from pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, isothiazolyl, imidazolyl, pyrrolyl, thiazolyl and triazolyl, said ring optionally substituted with 1 to 3 substituents selected from halogen, cyano and nitro, and C₁-C₄ alkyl, C_j- C₄ alkoxy and C_j-C₃ alkylthio, each optionally substituted with 1 to 5 halogen selected from fluorine and chlorine.

3. A compound of Claim 2 wherein

R¹ is C_]- C₂ alkyl or cyclopropyl, each optionally substituted with 1 to 3 halogen;

R³ and R⁴ are H;

R⁵ is methyl; and

Q is 3 -pyridinyl or 5 -thiazolyl optionally substituted with 1 or 2 substituents selected from halogen, cyano and nitro, and C₁-C₄ alkyl, CJ-C₄ alkoxy and Cj-C₃ alkylthio, each optionally substituted with 1 to 3 halogen selected from fluorine and chlorine.

4. A compound of Claim 3 wherein

R¹ is methyl, CH₂CF₃, CH₂CF₂H or cyclopropyl; and

Q is 3-pyridinyl or 5-thiazolyl optionally substituted with 1 or 2 substituents selected from halogen, methyl, methoxy and trifiuoromethyl.

5. A compound of Claim 4 wherein the nonhydrogen substituent(s) on the 3- pyridinyl or 5-thiazolyl of Q are bonded to ring atom(s) not adjacent to the ring atom connecting Q to the remainder of Formula 1.

6. A compound of Claim 1 that is selected from the group consisting of 4-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-2(5H)-oxazolone; 4-[[(6-chloro-3-pyridinyl)methyl]methylamino]-2(5i/)-oxazolone; 4-[[(2-chloro-5-thiazoyl)methyl]methylamino]-2(5H)-oxazolone;

4-[[ 1 -(2-chloro-5-thiazoyl)methyl]ethylamino]-2(5H)-oxazolone;

4-[[(2-chloro-5-thiazoyl)methyl]cyclopropylamino]-2(5H)-oxazolone;

4-[[(6-chloro-3-pyridinyl)methyl]ethylamino]-2(5H)-oxazolone;

4-[[(6-fluoro-3-pyridinyl)methyl]methylamino]-2(5H)-oxazolone;

4-[cyclopropyl[(6-fluoro-3-pyridinyl)methyl]amino]-2(5H)-oxazolone;

4-[[(5,6-dichloro-3-pyridinyl)methyl]methylamino]-2(5H)-oxazolone;

4-[cyclopropyl[(5,6-dichloro-3-pyridinyl)methyl]amino]-2(5H)-oxazolone; 117

4-[[(6-bromo-3-pyridinyl)memyl]methylamino]-2(5H)-oxazolone;

4-[[(6-bromo-3-pyridinyl)methyl]cyclopropylamino]-2(5H)-oxazolone;

4-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-5-methyl-2(5i/)-oxazolone;

4-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-2(5H)-thiazolone;

3-[[(6-chloro-3-pyridinyl)methyl]methylamino]-2-methyl-l,2,4-oxadiazol-5(2H)-one;

3-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-2-methyl-l,2,4-oxadiazol-5(2H)- one; and

3-[[(2-chloro-5-thiazolyl)methyl]cyclopropylamino]-2-methyl-l,2,4-oxadiazol-5(2Η)- one.

7. A composition comprising a compound of Claim 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

8. The composition of Claim 7 wherein said composition further comprises at least one additional biologically active compound or agent.

9. The composition of Claim 8 wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, bistrifluron, borate, 3-bromo-l-(3-chloro-2- pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-lH-pyrazole-5- carboxamide, buprofezin, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma- cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, ^"fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate, halofenozide, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, tebufenozide, 118 tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin, thiacloprid, thiamethoxani, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumuron, all strains of Bacillus thuringiensis, entomopathogenic bacteria, all strains of Nucleo polyhydrosis viruses, entomopathogenic viruses and entomopathogenic fungi.

10. The composition of Claim 9 wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acetamiprid, amitraz, avermectin, azadirachtin, bifenthrin, 3-bromo-l-(3-chloro-2-pyridinyl)-N-[4-cyano- 2-methyl-6-[(methylamino)carbonyl]phenyl]-lH-pyrazole-5-carboxamide, buprofezin, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyfluthrin, beta- cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, tebufenozide, thiacloprid, thiamethoxam, thiodicarb, thiosultap- sodium, tralomethrin, triazamate, triflumuron, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, nucleopolyhedro viruses and encapsulated delta-endotoxins of Bacillus thuringiensis.

11. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Claim 1.

12. The method of Claim 11 wherein the environment is a plant.

13. The method of Claim 11 wherein the environment is a seed.

14. The method of Claim 13 wherein the seed is coated with the compound of Claim 1 formulated as a composition comprising a film former or adhesive agent.

15. A treated seed comprising a compound of Claim 1 in an amount of from about 0.0001 to 1% by weight of the seed before treatment.