3-arylphenyl sulfide derivative and insecticide and miticide

• US 6,509,354 B1
• Filed: 10/27/2000
• Issued: 01/21/2003
• Est. Priority Date: 04/27/1998
• Status: Expired due to Term

• Current Assignee: Ihara Chemical Industry Co., Ltd., Kumiai Chemical Industry Company Limited
• Original Assignee: Ihara Chemical Industry Co., Ltd., Kumiai Chemical Industry Company Limited
• Inventors: Yano, Hiroyuki, Toriyabe, Keiji, Komatsu, Masaaki, Itou, Minoru, Nishiyama, Kiyotoshi, Wada, Nobuhide, Fujisawa, Toyokazu, Asahida, Mitsuharu, Maeda, Yasunobu, Tada, Osamu, Takefuji, Nobuo, Hirade, Tetsuya
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): TRUONG, TAMTHOM NGO
• Application Number:
  US09/673,633
• Time in Patent Office: 816 Days
• Field of Search: 514/222.2, 514/228.8, 514/241, 514/252.01, 514/252.1, 514/256, 514/277, 514/317, 514/709, 544/3, 544/63, 544/179, 544/180, 544/239, 544/242, 544/298, 544/336, 546/243, 562/45
• US Class Current: 514/317
• CPC Class Codes: A01N 31/08 Oxygen or sulfur directly attached to an aromatic ring system
• CPC Class Codes: A01N 31/14 Ethers
• CPC Class Codes: A01N 33/10 having at least one oxygen or sulfur atom directly attached to an aromatic ring system
• CPC Class Codes: A01N 37/08 containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
• CPC Class Codes: A01N 37/34 Nitriles
• CPC Class Codes: A01N 41/10 Sulfones; Sulfoxides
• CPC Class Codes: A01N 43/08 with oxygen as the ring hetero atom
• CPC Class Codes: A01N 43/10 with sulfur as the ring hetero atom
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 47/18 containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic 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 317/48 the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
• CPC Class Codes: C07C 323/18 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
• CPC Class Codes: C07C 323/20 with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 323/36 the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
• CPC Class Codes: C07C 323/63 : the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
• CPC Class Codes: C07D 213/12 : from unsaturated compounds
• CPC Class Codes: C07D 213/32 : Sulfur atoms
• CPC Class Codes: C07D 213/48 : Aldehydo radicals
• CPC Class Codes: C07D 213/57 : Nitriles
• CPC Class Codes: C07D 213/64 : attached in position 2 or 6
• CPC Class Codes: C07D 239/36 : as doubly bound oxygen atom or as unsubstituted hydroxy radical
• CPC Class Codes: C07D 239/38 : One sulfur atom
• CPC Class Codes: C07D 239/40 : as doubly bound sulfur atom or as unsubstituted mercapto radical
• CPC Class Codes: C07D 249/08 : 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: C07D 333/24 : Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

3-Arylphenyl sulfide derivatives represented by general formula (I):

(wherein R is a C₂-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group or the like, B₀ to B₂ and B₃ are hydrogen atoms, halogen atoms, cyano groups, C₁-C₄ haloalkyl groups or the like, n is 0, 1 or 2, and Ar is a phenyl ring, a pyridine ring, a thiophene ring, a pyrazole ring or the like), and insecticides and miticides containing the 3-arylphenyl sulfide derivatives as an active ingredient.

Claims

1. A 3-arylphenyl sulfide compound represented by general formula (I):

wherein;

R is a C₂-C₆ alkyl group, which may be substituted by one or more halogen atoms or cyano groups;

a C₂-C₆ alkenyl group which may be substituted by one or more halogen atoms or cyano groups;

a C₂-C₆ alkynyl group which may be substituted by one or more halogen atoms or cyano groups;

a C₃-C₆ cycloalkyl group which may be substituted by one or more halogen atoms or cyano groups;

or a C₄-C₉ cycloalkylalkyl group which may be substituted by one or more halogen atoms or cyano groups;

n is an integer of from 0 to 2,

Ar is a group represented by any one of general formulae;

 

wherein

Q₁ is C-A,

Q₂, is C-A₂,

Q₃, is C-A₃,

Q₄ is C-A₄, and

Q₅ is C-A_5,;

wherein A₁ and A₅ are hydrogen atoms,

wherein B₀ is selected from the group consisting of a hydrogen atom, halogen atom, amino group, cyano group, nitro group, C₁-C₆ alkyl group, and a C₁-C₄ haloalkyl group;

wherein A₂, A₃, A₄, B₁, B₂ and B₃ are selected from the group consisting of a hydrogen atom, halogen atom, cyano group, nitro group, C₁-C₆ alkyl group which may be substituted by one or more halogen atoms, hydroxyl groups, cyano groups, C₂-C₇ alkoxycarbonyl groups or C₁-C₆ alkoxy groups;

C₂-C₆ alkenyl group which may be substituted by one or more halogen atoms or cyano groups, C₂-C₆ alkynyl group which may be substituted by one or more halogen atoms or cyano groups;

C₁-C₇ acyl group;

C₂-C₅ haloalkylcarbonyl group;

carboxyl group; and

C₂-C₇ alkoxycarbonyl group;

provided that;

when Ar is represented by general formula (Ar-1) then A₂, A₃, A₄ and B₂ are not simultaneously hydrogen atoms;

when all of A₁ to A₅ are hydrogen atoms, then compounds wherein B₂ is a methyl group, and R is an isopropyl are excluded.

2. The compound according to claim 1, wherein Ar is represented by general formula (Ar-1).

3. The compound according to claim 1, wherein Ar is represented by general formula (Ar-2).

4. An insecticide or miticide comprising the 3-arylphenyl sulfide compound as defined in claim 1.

5. A method of controlling or killing a farm or garden pest, insect or mite comprising contacting said pest, insect or mite with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.

6. An insecticide or miticide comprising the 3-arylphenyl sulfide compound as defined in claim 2.

7. A method of controlling or killing a farm or garden pest, insect or mite comprising contacting said pest, insect or mite with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 2.

8. An insecticide or miticide comprising the 3-arylphenyl sulfide compound as defined in claim 3.

9. A method of controlling or killing a farm or garden pest, insect or mite comprising contacting said pest, insect or mite with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 3.

10. The compound of claim 1, wherein R is a C₃-C₆ alkyl group, which may be substituted by one or more halogen atoms or cyano groups;

C₂-C₆ alkenyl group which may be substituted by one or more halogen atoms or cyano groups;

a C₂-C₆ alkynyl group which may be substituted by one or more halogen atoms or cyano groups;

a C₃-C₆ cycloalkyl group which may be substituted by one or more halogen atoms or cyano groups;

or a C₄-C₉ cycloalkylalkyl group which may be substituted by one or more halogen atoms or cyano groups.

11. The compound of claim 1, wherein B₀ is selected from the group consisting of a hydrogen atom, amino group, cyano group, nitro group, C₁-C₆ alkyl group, and a C₁-C₄ haloalkyl group.

12. The compound of claim 1, wherein B₀ is hydrogen.

13. The compound of claim 1, wherein B₀ is selected from the group consisting of an amino group, cyano group, nitro group, C₁-C₆ alkyl group, and a C₁-C₄ haloalkyl group.

14. A composition comprising the compound of claim 1 and one or more compounds selected from the group consisting of an adjuvant, surfactant and carrier.

15. A composition comprising the compound of claim 1 and one or more compounds selected from the group consisting of a fertilizer, antivirus agent, fungicide, attractant, herbicide, plant growth regulator, insecticide, a miticide and nematacide.

16. A method of controlling or killing a mite comprising contacting said mite with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.

17. A method of controlling or killing a lepidopteran comprising contacting said lepidopteran with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.

18. A method of controlling or killing a hemipteran comprising contacting said hemipteran with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.

19. A method of controlling or killing a dipteran comprising contacting said dipteran with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.

20. A method of controlling or killing a hymenopteran comprising contacting said hymenopteran with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.

21. A method of controlling or killing a orthopteran comprising contacting said orthopteran with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.

22. A method of controlling or killing a isopteran comprising contacting said isopteran with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.

23. A method of controlling or killing a nematode comprising contacting said nematode with an effective amount of the 3-arylphenyl sulfide compound as defined in claim 1.