Quinoline derivatives and insecticide comprising thereof as active ingredient

1. A compound represented by formula (I) or an agriculturally and horticulturally acceptable acid addition salt thereof:

wherein

R 1 represents a hydrogen atom; or COR 4 wherein R 4 represents C 1-4 alkyl, OR 5 wherein R 5 represents C 1-4 alkyl, or NR 6 R 7 wherein R 6 and R 7 each independently represent a hydrogen atom or C 1-18 alkyl,

R 2 represents C 1-4 alkyl,

R 3 represents C 1-4 alkyl,

alternatively R 2 and R 3 together represent —(CH 2 ) m — wherein m is 3 or 4,

X 1 and X 2 , each independently represent a hydrogen atom, a halogen atom, C 1-4 alkyl optionally substituted by halogen atom, C 1-4 alkyloxy, or C 1-4 alkyloxycarbonyl,

provided that X 1 and X 2 do not simultaneously represent a hydrogen atom,

X 3 represents a hydrogen atom,

W 1 represents a nitrogen atom or C—Y 1 ,

W 2 represents a nitrogen atom or C—Y 2 ,

W 3 represents a nitrogen atom or C—Y 3 ,

provided that, when W 1 represents a nitrogen atom, W 2 and W 3 represent C—Y 2 and C—Y 3 , respectively; when W 2 represents a nitrogen atom, W 1 and W 3 represent C—Y 1 and C—Y 3 , respectively; and when W 3 represents a nitrogen atom, W 1 and W 2 represent C—Y 1 and C—Y 2 , respectively,

Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 each independently represent a hydrogen atom, A, or B,

provided that W 1 , W 2 , and W 3 respectively represent C—Y 1 , C—Y 2 , and C—Y 3 , and, when Z represents a bond, methylene optionally substituted by one or two methyl groups, or an oxygen atom, at least one of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 represents A,

wherein A represents a group selected from the group consisting of:

C 1-8 alkyl which is substituted by one or more groups selected from one or more halogen atoms which may be the same or different, C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different, and C 2-4 alkenyloxy substituted by one or more halogen atoms which may be the same or different;

C 2-8 alkenyl which is substituted by one or more groups selected from one or more halogen atoms which may be the same or different, C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different, and C 2-4 alkenyloxy substituted by one or more halogen atoms which may be the same or different;

C 1-8 alkyloxy which is substituted by one or more groups selected from one or more halogen atoms which may be the same or different, C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different, and C 2-4 alkenyloxy substituted by one or more halogen atoms which may be the same or different;

C 2-8 alkenyloxy which is substituted by one or more groups selected from one or more halogen atoms which may be the same or different, C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different, and C 2-4 alkenyloxy substituted by one or more halogen atoms which may be the same or different;

C 1-8 alkyloxycarbonyl which is optionally substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different;

C 1-8 alkylthio which is optionally substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different;

C 2-8 alkenylthio which is optionally substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different;

C 1-8 alkylsulfinyl which is optionally substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different;

C 2-8 alkenylsulfinyl which is optionally substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different;

C 1-8 alkylsulfonyl which is optionally substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different;

C 2-8 alkenylsulfonyl which is optionally substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different;

phenyl which is substituted by one or more halogen atoms which may be the same or different, C 1-4 alkyl substituted by one or more halogen atoms which may be the same or different, or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different; and

phenoxy which is substituted by one or more halogen atoms which may be the same or different, C 1-4 alkyl substituted by one or more halogen atoms which may be the same or different, or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different,

B represents a group selected from the group consisting of a halogen atom, C 1-4 alkyl, C 1-4 alkyloxy, nitro, and cyano,

alternatively adjacent two of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 may together represent

—O—(CH 2 ) n —O— optionally substituted by halogen atom,

—(CH 2 ) n ——O— optionally substituted by halogen atom,

—S—(CH 2 ) n —S— optionally substituted by halogen atom,

—(CH 2 ) n —S— optionally substituted by halogen atom, or

—(CH 2 ) n — optionally substituted by halogen atom,

wherein n is 1, 2, or 3,

Z represents an oxygen atom, OCH 2 , or O(CH 2 ) 3 O.

2. The compound according to claim 1 , wherein

W 1 , W 2 , and W 3 represent C—Y 1 , C—Y 2 , and C—Y 3 , respectively,

Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 each independently represent a hydrogen atom, A or B,

provided that, when Z represents a bond, methylene optionally substituted by one or two methyl, or an oxygen atom, at least one of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 represents A,

wherein A represents a group selected from the group consisting of:

C 1-8 alkyl which is substituted by one or more halogen atoms which may be the same or different;

C 1-8 alkyloxy which is substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different;

C 1-8 alkyloxycarbonyl;

C 1-8 alkylthio which is substituted by one or more halogen atoms which may be the same or different;

C 1-8 alkylsulfonyl which is subsituted by one or more halogen atoms which may be the same or different;

phenyl which is substituted by one or more halogen atoms which may be the same or different, or C 1-4 alkyl substituted by one or more halogen atoms which may be the same or different; and

phenoxy which is substituted by one or more halogen atoms which may be the same or different, or C 1-4 alkyl substituted by one or more halogen atoms which may be the same or different,

B represents a group selected from the group consisting of a halogen atom, C 1-4 alkyl, C 1-4 alkyloxy, and cyano,

alternatively adjacent two of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 may together represent —O—(CH 2 ) n —O— substituted by one or more halogen atoms, wherein n is 1 or 2.

3. The compound according to claim 1 , wherein

any one of W 1 , W 2 , and W 3 represents a nitrogen atom, and the other two groups represent the corresponding C—Y 1 , C—Y 2 , or C—Y 3 , and

Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 each independently represent a hydrogen atom; C 1-8 alkyl substituted by one or more halogen atoms which may be the same or different; or a halogen atom.

4. The compound according to claim 1 , wherein

W 1 , W 2 , and W 3 represent C—Y 1 , C—Y 2 , and C—Y 3 , respectively, and

Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 each independently represent a hydrogen atom; C 1-8 alkyl which is substituted by one or more halogen atoms which may be the same or different; C 1-8 alkyloxy which is substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different; C 1-8 alkylthio which is substituted by one or more halogen atoms which may be the same or different; or a halogen atom,

provided that at least one of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 represents C 1-8 alkyl which is substituted by one or more halogen atoms which may be the same or different; C 1-8 alkyloxy which is substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different; or C 1-8 alkylthio which is substituted by one or more halogen atoms which may be the same or different,

alternatively adjacent two of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 may together represent —O—(CH 2 ) n —O— substituted by one or more halogen atoms, wherein n is 1 or 2.

5. The compound according to claim 1 , wherein

R 1 represents a hydrogen atom; or COR 4 wherein R 4 represents C 1-4 alkyl, OR 5 wherein R 5 represents C 1-4 alkyl, or NR 6 R 7 wherein R 6 and R 7 each independently represent a hydrogen atom or C 1-18 alkyl,

R 2 represents C 1-4 alkyl,

R 3 represents C 1-4 alkyl,

alternatively R 2 and R 3 together represent —(CH 2 ) m — wherein m is 3 or 4,

X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, C 1-4 alkyl optionally substituted by halogen atom, C 1-4 alkyloxy, or C 1-4 alkyloxycarbonyl,

provided that X 1 and X 2 do not simultaneously represent a hydrogen atom,

X 3 represents a hydrogen atom,

W 1 , W 2 , and W 3 represent C—Y 1 , C—Y 2 , and C—Y 3 , respectively, and

Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 each independently represent a hydrogen atom; C 1-8 alkyl which is substituted by one or more halogen atoms which may be the same or different; C 1-8 alkyloxy which is substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different; C 1-8 alkylthio which is substituted by one or more halogen atoms which may be the same or different; or a halogen atom,

provided that at least one of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 represents C 1-8 alkyl which is substituted by one or more halogen atoms which may be the same or different; C 1-8 alkyloxy which is substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different; or C 1-8 alkylthio which is substituted by one or more halogen atoms which may be the same or different,

alternatively adjacent two of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 may together represent —O—(CH 2 ) n —O— substituted by one or more halogen atoms, wherein n is 1 or 2, and

Z represents an oxygen atom, OCH 2 , or O(CH 2 ) 3 O.

6. The compound according to claim 1 , wherein

R 1 represents COR 4 or COOR 5 wherein R 4 and R 5 represent C 1-4 alkyl,

R 2 represents C 1-4 alkyl,

R 3 represents C 1-4 alkyl,

X 1 and X 2 each independently represent a hydrogen atom, or C 1-4 alkyl optionally substituted by halogen atom,

provided that X 1 and X 2 do not simultaneously represent a hydrogen atom,

X 3 represents a hydrogen atom,

W 1 , W 2 , and W 3 represent C—Y 1 , C—Y 2 , and C—Y 3 , respectively,

Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 each independently represent a hydrogen atom; C 1-8 alkyloxy which is substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different; or a halogen atom,

provided that at least one of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 represents C 1-8 alkyloxy which is substituted by one or more halogen atoms which may be the same or different, and/or C 1-4 alkyloxy substituted by one or more halogen atoms which may be the same or different,

alternatively adjacent two of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 may together represent —O—(CH 2 ) n —O— substituted by one or more halogen atoms, wherein n is 1 or 2, and Z represents an oxygen atom.

7. An agricultural or horticultural insecticide composition comprising as an active ingredient a compound according to any one of claims 2 , 3 , and 4 to 6 or an agriculturally and horticulturally acceptable acid addition salt thereof, and a suitable carrier, surfactant, dispersant and/or adjuvant.

8. A method for controlling an agricultural and horticultural insect pest, comprising the step of applying an effective amount of a compound according to any one of claims 2 , 3 , and 4 to 6 or an agriculturally and horticulturally acceptable acid addition salt thereof to a plant or soil.

9. The method according to claim 8 , wherein said insect pest is selected from the group consisting of Lepidoptera, Hemiptera, Coleoptera, Acari, Hymenoptera, Orthoptera, Diptera, Thysanoptera, and plant parasitic nematoda.