Ether compounds with nitrogen-containing 5-member heterocycle and uses thereof

• US 8,222,280 B2
• Filed: 11/25/2009
• Issued: 07/17/2012
• Est. Priority Date: 11/28/2008
• Status: Active Grant

• Current Assignee: Shenyang Sinochem Agrochemicals R&D Co., Ltd. (Jiangsu Yangnong Chemical Company Limited)
• Original Assignee: Shenyang Research Institute of Chemical Industry Co. Ltd. (Sinochem Group Co., Ltd.), Sinochem Corporation (Sinochem Group Co., Ltd.)
• Inventors: Liu, Changling, Li, Miao, Zhang, Hong, Wang, Junfeng, Zhang, Jinbo, Hao, Shulin, Zhang, Jing, Yang, Jichun
• Primary Examiner(s): Anderson, Rebecca
• Assistant Examiner(s): SHTERENGARTS, SAMANTHA L
• Application Number:
  US13/121,334
• Publication Number:
  US 20110178149A1
• Time in Patent Office: 965 Days
• Field of Search: 548/370.4, 548/203, 548/373.1, 514/341, 514/365, 514/406, 546/275.4
• US Class Current: 514/341
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 407/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond

Abstract

The invention relates to ether compounds with nitrogen-containing 5-member heterocycle, represented by formula (I):

The groups are as defined as specification.

The compounds of the present invention have broad-spectrum insecticidal activities, and they are very effective to lepidopterous pests, including Ostrinia nubilalis, sugarcane borer, summer fruit tortrix moth, Grapholitha inopinata, Lymantria dispar, Cnaphalocrocis medialis, Pyrausta nubilalis, Heliothis assulta, Grapholitha molesta, Plutella xylostella, Laphygma exigua, Prodenialitura and the like, especially more effective to Plutella xylostella and Laphygma exigua, and can have very good effects at very low doses. And the compounds of present invention have high activities to homopteran pests such as aphid. At the same time, some compounds of present invention have very good fungicidal activities, and can be used for preventing wheat powdery mildew, cucumber downy mildew, vegetable grey mould and the like.

Claims

1. Ether compounds with nitrogen-containing 5-member heterocycle represented by general formula (I):

2. The compounds according to claim 1, wherein in general formula (I-1) or formula (I-2):

R₁ is selected from H, CO₂R₆, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆haloalkoxyC₁-C₆alkyl, C₃-C₆cycloalkyl or R₇;

R₂ is selected from H, F, Cl, Br, CN, CO₂R₆ or C₁-C₆alkyl;

R₄ and R₅ mutually independently may be the same or different, selected from H or Cl;

X is NR₈;

R₈ is selected from C₁-C₄alkyl or R₇;

R₆ is selected from H or C₁-C₄alkyl;

R₇ is selected from phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy or C₁-C₆alkylthio;

Q is selected from —

CH₂CH₂—

, —

CH₂CH₂CH₂—

or —

CH₂CH₂CH₂CH₂—

.

3. The compounds according to claim 1, wherein in general formula (I-3):

R₁ is selected from H, CO₂R₆ or C₁-C₆alkyl;

R₂ is selected from H, F, Cl, Br or C₁-C₆alkyl;

R₄ and R₅ mutually independently may be the same or different, selected from H or Cl;

X is NR₈;

R₈ is selected from C₁-C₄alkyl or R₇;

R₆ is selected from H or C₁-C₄alkyl;

R₇ is selected from phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, CN, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy or C₁-C₆alkylthio;

Q is selected from —

CH₂CH₂—

, —

CH₂CH₂CH₂—

or —

CH₂CH₂CH₂CH₂—

.

4. The compounds according to claim 2, wherein in general formula (I-1) or formula (I-2):

R₁ is selected from H, C₁-C₆alkyl, phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy or C₁-C₄alkylthio;

R₂ is selected from H, C₁ or C₁-C₄alkyl;

R₄ and R₅ mutually independently may be the same or different, selected from H or Cl;

X is NR₈;

R₈ is selected from C₁-C₄alkyl, phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, C₁-C₄allyl, C₁-C₄haloalkyl, C₁-C₄alkoxy or C₁-C₄haloalkoxy;

R₆ is selected from H or C₁-C₄alkyl;

Q is selected from —

CH₂CH₂—

, —

CH₂CH₂CH₂—

or —

CH₂CH₂CH₂CH₂—

.

5. The compounds according to claim 3, wherein in general formula (I-3):

R₁ is selected from H, CO₂R₆ or C₁-C₄alkyl;

R₂ is selected from H, F, Cl, Br or C₁-C₄alkyl;

R₄ and R₅ mutually independently may be the same or different, selected from H or Cl;

X is NR₈;

R₈ is selected from C₁-C₄alkyl, phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy or C₁-C₄haloalkoxy;

R₆ is selected from H or C₁-C₄alkyl;

Q is selected from —

CH₂CH₂—

, —

CH₂CH₂CH₂—

or —

CH₂CH₂CH₂CH₂—

.

6. A method of controlling insects which comprises applying a compound having general formula (I) according to claim 1 to agricultural and other fields.

7. A method of controlling fungi which comprises applying a compound having general formula (I) according to claim 1 to agricultural and other fields.

8. An insecticidal or fungicidal composition comprising a compound having general formula (I) of claim 1 as an active ingredient, wherein the weight percentage of the active ingredient in the composition is from 0.1-99%.