ACID AMIDE DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND PESTICIDES CONTAINING THEM

• US 20100093707A1
• Filed: 12/17/2009
• Published: 04/15/2010
• Est. Priority Date: 09/18/2001
• Status: Active Grant

• Current Assignee: Ishihara Sangyo Kaisha Limited
• Original Assignee: Ishihara Sangyo Kaisha Limited
• Inventors: Izakura, Kenji, NAKAMURA, Yuji, Morita, Masayuki, Yoneda, Tetsuo
• Granted Patent: US 8,093,241 B2
• Time in Patent Office: Days
• US Class Current: 514/224.2
• CPC Class Codes: A01N 37/20 containing the group , wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: A61P 33/14 Ectoparasiticides, e.g. scabicides
• CPC Class Codes: C07C 233/76 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
• CPC Class Codes: C07C 307/02 Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
• CPC Class Codes: C07C 309/65 of a saturated carbon skeleton
• CPC Class Codes: C07C 309/66 Methanesulfonates
• CPC Class Codes: C07C 311/08 having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 317/32 with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07C 323/42 Y being a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 329/06 having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
• CPC Class Codes: C07D 209/14 Radicals substituted by nitrogen atoms, not forming part of a nitro radical
• CPC Class Codes: C07D 213/50 Ketonic radicals
• CPC Class Codes: C07D 213/61 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 317/46 condensed with one six-membered ring
• CPC Class Codes: C07D 317/58 Radicals substituted by nitrogen atoms nitro radicals C07D317/52
• CPC Class Codes: C07D 319/20 with substituents attached to the hetero ring
• CPC Class Codes: C07D 333/22 Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
• CPC Class Codes: C07D 333/28 Halogen atoms

Abstract

The present invention relates to an acid amid derivative of the formula (I) or a salt thereof:

wherein A is phenyl which may be substituted by X, benzyl which may be substituted by X, naphthyl which may be substituted by X, a heterocyclic group which may be substituted by X, a fused heterocyclic group which may be substituted by X, indanyl (the indanyl may be substituted by halogen, alkyl or alkoxy) or tetrahydronaphthyl (the tetrahydronaphthyl may be substituted by halogen, alkyl or alkoxy), B is alkyl, cycloalkyl, phenyl which may be substituted by Y, a heterocyclic group which may be substituted by Y, or a condensed heterocyclic group which may be substituted by Y, each of R₁ and R₂ is alkyl, cyano or —CO₂R₁₄, or R₁ and R₂ may together form a 3- to 6-membered saturated carbocyclic ring, R₃ is hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, —COR₁₅, —S(O)mR₁₆ or —S(O)nNR₁₇R₁₈, which is useful as an active ingredient of pesticides.

Claims

1. An acid amide derivative of the formula (I) or a salt thereof:

wherein A is a fused heterocyclic group which may be substituted by X, B is phenyl which may be substituted by Y, X is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted by Y, phenoxy which may be substituted by Y, benzyloxy which may be substituted by Y, pyridyloxy which may be substituted by Y, —

OR₄, —

SR₅, —

NR₆R₇, —

CO₂R₈,

—

C(═

O)NR₉R₁₀or an unsaturated heterocyclic group (the unsaturated heterocyclic ring may be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, —

OR₄, —

CO₂R₁₁, —

CONR₁₂R₁₃ or an unsaturated heterocyclic group (the unsaturated heterocyclic ring may be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), each of R₁ and R₂ is alkyl, cyano or —

CO₂R₁₄, or R₁ and R₂ may together form a 3- to 6-membered saturated carbocyclic ring, R₃ is hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, —

COR₁₅,

—

S(O)mR₁₆ or —

S(O)nNR₁₇R₁₈, each of R₄ and R₆ is hydrogen, —

C(═

W)R₁₉, —

C(═

W)OR₂₀, —

C(═

W)SR₂₁, —

C(═

W)NR₂₂R₂₃, —

S(O)qR₂₄ or —

S(O)rNR₂₅R₂₆, R₅ is hydrogen, —

C(═

W)R₁₉, —

C(═

W)OR₂₀, —

C(═

W)SR₂₁ or

—

C(═

W)NR₂₂R₂₃, R₇ is hydrogen, alkyl or haloalkyl, each of R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃ and R₁₄ is hydrogen or alkyl, R₁₅ is hydrogen, alkyl or alkoxy, each of R₁₆, R₁₇, R₁₈, R₁₉, R₂₀, R₂₁, R₂₂, R₂₃, R₂₄, R₂₅ and R₂₆ is alkyl, haloalkyl or phenyl (the phenyl which may be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), each of m, n, q and r is from 0 to 2, W is oxygen or sulfur.

7. The acid amide derivative or a salt thereof according to claim 1, wherein the fused heterocyclic group is a 8- to 10-membered fused heterocyclic group containing from 1 to 4 atoms of at least one type selected from the group consisting of O, S and N.

8. The acid amide derivative or a salt thereof according to claim 7, wherein the fused heterocyclic group is benzofuranyl, isobenzofuranyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, benzothienyl, isobenzothienyl, dihydrobenzothienyl, dihydroisobenzothienyl, tetrahydrobenzothienyl, indolyl, isoindolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl, isochromanyl, chromonyl, chromanonyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, imidazopyridyl, naphthyridinyl, pteridinyl, dihydrobenzoxazinyl, dihydrobenzoxazolinonyl, dihydrobenzoxazinonyl or benzothioxanyl.

11. A pesticide which contains the acid amide derivative or a salt thereof as defined in claim 1, as an active ingredient.

12. An agricultural or horticultural pesticide which contains the acid amide derivative or a salt thereof as defined in claim 1, as an active ingredient.

13. An insecticide, miticide or nematicide which contains an acid amide derivative or a salt thereof as defined in claim 1, as an active ingredient.

14. A nematicide which contains an acid amide derivative or a salt thereof as defined in claim 1, as an active ingredient.

15. An agent for controlling parasites on animals, which contains an acid amide derivative or a salt thereof as defined in claim 1, as an active ingredient.

16. An agent for controlling parasites in the bodies of animals, which contains an acid amide derivative or a salt thereof as defined in claim 1, as an active ingredient.

17. An agent for preventing or curing animal diseases caused by parasites, which contains an acid amide derivative or a salt thereof as defined in claim 1, as an active ingredient.

18. A method for controlling a pest, which comprises using an effective amount of an acid amide derivative or a salt thereof as defined in claim 1.

2-6. -6. (canceled)

9. (canceled)

10. A process for producing an acid amide derivative of the formula (I) or a salt thereof:

wherein A is a fused heterocyclic group which may be substituted by X, B is alkyl, cycloalkyl, phenyl which may be substituted by Y, X is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted by Y, phenoxy which may be substituted by Y, benzyloxy which may be substituted by Y, pyridyloxy which may be substituted by Y, —

OR₄, —

SR₅, —

NR₆R₇, —

CO₂R₈,

—

C(═

O)NR₉R₁₀ or an unsaturated heterocyclic group (the unsaturated heterocyclic ring may be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, —

OR₄, —

CO₂R₁₁, —

CONR₁₂R₁₃ or an unsaturated heterocyclic group (the unsaturated heterocyclic ring may be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), each of R₁ and R₂ is alkyl, cyano or —

CO₂R₁₄, or R₁ and R₂ may together form a 3- to 6-membered saturated carbocyclic ring, R₃ is hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, —

COR₁₅,

—

S(O)mR₁₆ or —

S(O)nNR₁₇R₁₈, each of R₄ and R₆ is hydrogen, —

C(═

W)R₁₉, —

C(═

W)OR₂₀, —

C(═

W)SR₂₁,

—

C(═

W)NR₂₂R₂₃, —

S(O)qR₂₄ or —

S(O)rNR₂₅R₂₆, R₅ is hydrogen, —

C(═

W)R₁₉, —

C(═

W)OR₂₀, —

C(═

W)SR₂₁ or

C(═

W)NR₂₂R₂₃, R₇ is hydrogen, alkyl or haloalkyl, each of R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃ and R₁₄ is hydrogen or alkyl, R₁₅ is hydrogen, alkyl or alkoxy, each of R₁₆, R₁₇, R₁₈, R₁₉, R₂₀, R₂₁, R₂₂, R₂₃, R₂₄, R₂₅ and R₂₆ is alkyl, haloalkyl or phenyl (the phenyl which may be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), each of m, n, q and r is from 0 to 2, W is oxygen or sulfur, which comprises (1) reacting a compound of the formula (II) or a salt thereof;

wherein A, R₁ and R₂ are as defined above, with a compound of the formula (III);

B—

COZ  

 

(III)

wherein B is as defined above, and Z is hydroxy, alkoxy or halogen, or (2) reacting a compound of the formula (I-1);

wherein A, B, R₁ and R₂ are as defined above, with a compound of the formula (IV);

R_3a—

T  

 

(IV)

wherein R_3a is alkyl, alkoxyalkyl, alkylthioalkyl,

—

COR₁₅, —

S(O)mR₁₆ or —

S(O)nNR₁₇R₁₈, R₁₅, R₁₆, R₁₇, R₁₈, m and n are as defined above, and T is halogen.