Ether compounds with nitrogen-containing 5-member heterocycle and uses thereof
View Patent ↗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.
1. Ether compounds with nitrogen-containing 5-member heterocycle represented by general formula (I):
Wherein:
R 1 is selected from H, CO 2 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 haloalkoxyC 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or R 7 ;
R 2 is selected from H, halo, CN, CO 2 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 6 cycloalkyl or R 7 ;
R 3 is Cl;
R 4 and R 5 mutually independently may be the same or different, selected from H or Cl;
X is selected from NR 8 or O;
R 8 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or R 7 ;
Y 1 and Y 2 are Cl;
A 1 and A 2 are O;
R 6 is selected from H or C 1 -C 6 alkyl;
R 7 is selected from phenyl, pyridinyl, furanyl, thiophen, thiazolyl or benzyl, or above group substituted with 1-3 substitutents selected from halo, NO 2 , CN, CO 2 R 6 , CONHR 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, phenyl, 4-chloro-phenyl, phenoxy or 4-chloro-phenoxy;
Q is selected from —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —;
A 2 links with heterocycle at the 3, 4 or 5-position; when A 2 links with heterocycle at the 5-position, R 1 is at 3-position, R 2 is at 4-position, the structure is represented by general formula I-1; when A 2 links with heterocycle at the 3-position, R 1 is at 5-position, R 2 is at 4-position, the structure is represented by general formula I-2; when A 2 links with heterocycle at the 4-position, R 1 is at 3-position, R 2 is at 5-position, the structure is represented by general formula I-3;
2. The compounds according to claim 1 , wherein in general formula (I-1) or formula (I-2):
R 1 is selected from H, CO 2 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 haloalkoxyC 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or R 7 ;
R 2 is selected from H, F, Cl, Br, CN, CO 2 R 6 or C 1 -C 6 alkyl;
R 4 and R 5 mutually independently may be the same or different, selected from H or Cl;
X is NR 8 ;
R 8 is selected from C 1 -C 4 alkyl or R 7 ;
R 6 is selected from H or C 1 -C 4 alkyl;
R 7 is selected from phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio;
Q is selected from —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —.
3. The compounds according to claim 1 , wherein in general formula (I-3):
R 1 is selected from H, CO 2 R 6 or C 1 -C 6 alkyl;
R 2 is selected from H, F, Cl, Br or C 1 -C 6 alkyl;
R 4 and R 5 mutually independently may be the same or different, selected from H or Cl;
X is NR 8 ;
R 8 is selected from C 1 -C 4 alkyl or R 7 ;
R 6 is selected from H or C 1 -C 4 alkyl;
R 7 is selected from phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, CN, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylthio;
Q is selected from —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —.
4. The compounds according to claim 2 , wherein in general formula (I-1) or formula (I-2):
R 1 is selected from H, C 1 -C 6 alkyl, phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio;
R 2 is selected from H, C 1 or C 1 -C 4 alkyl;
R 4 and R 5 mutually independently may be the same or different, selected from H or Cl;
X is NR 8 ;
R 8 is selected from C 1 -C 4 alkyl, phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, C 1 -C 4 allyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R 6 is selected from H or C 1 -C 4 alkyl;
Q is selected from —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —.
5. The compounds according to claim 3 , wherein in general formula (I-3):
R 1 is selected from H, CO 2 R 6 or C 1 -C 4 alkyl;
R 2 is selected from H, F, Cl, Br or C 1 -C 4 alkyl;
R 4 and R 5 mutually independently may be the same or different, selected from H or Cl;
X is NR 8 ;
R 8 is selected from C 1 -C 4 alkyl, phenyl, or phenyl substituted with 1-3 substitutents selected from F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R 6 is selected from H or C 1 -C 4 alkyl;
Q is selected from —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —.
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%.