Tetrazolinone compounds and their use as pesticides

1. A tetrazolinone compound of a formula (1):

wherein

Q represents a group selected from the following group: Q2, Q3 or Q4:

R 1 , R 2 , R 3 and R 11 represent independently of each other a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, a hydroxy group, a thiol group, an C2-C6 alkenyl group, a C2-C6 haloalkenyl group, an C2-C6 alkynyl group, a C2-C6 haloalkynyl group, an C1-C6 alkoxy group, a C1-C6 haloalkoxy group, an C1-C8 alkylamino group, a C1-C8 haloalkylamino group, an C1-C6 alkylthio group, a C1-C6 haloalkylthio group, an C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, an C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a C3-C9 trialkylsilyl group, an C2-C6 alkylcarbonyl group, an C2-C6 alkoxycarbonyl group, an C2-C8 alkylaminocarbonyl group, an C1-C6 alkyl group optionally having one or more groups selected from Group P 1 or an C3-C6 cycloalkyl group optionally having one or more groups selected from Group P 1 ;

R 4 and R 5 represent independently of each other a hydrogen atom, a halogen atom or an C1-C3 alkyl group;

R 6 represents a C3-C6 cycloalkyl group, an C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C1-C4 haloalkoxy group, an C1-C4 alkylthio group, an C1-C4 alkylsulfinyl group, an C1-C4 alkylsulfonyl group, a C1-C4 haloalkylthio group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, an C1-C6 alkylamino group, a C1-C6 haloalkylamino group or a C3-C6 halocycloalkyl group;

R 7 , R 8 and R 9 represent independently of each other a hydrogen atom, a halogen atom, an C1-C3 alkyl group, a C1-C3 haloalkyl group, an C2-C3 alkenyl group, a C2-C3 haloalkenyl group or an C1-C3 alkoxy group;

R 10 represents an C1-C3 alkyl group, a C1-C3 haloalkyl group, an C2-C3 alkenyl group, a C2-C3 haloalkenyl group, an C2-C3 alkynyl group, a C2-C3 haloalkynyl group, a C3-C5 cycloalkyl group or a C3-C5 halocycloalkyl group;

X represents an oxygen atom or a sulfur atom;

A 1 and A 3 represent independently of each other a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, a hydroxy group, a thiol group, an C2-C6 alkenyl group, a C2-C6 haloalkenyl group, an C2-C6 alkynyl group, a C2-C6 haloalkynyl group, an C1-C6 alkoxy group, a C1-C6 haloalkoxy group, an C1-C8 alkylamino group, a C1-C8 haloalkylamino group, an C1-C6 alkylthio group, a C1-C6 haloalkylthio group, an C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, an C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a C3-C9 trialkylsilyl group, an C2-C6 alkylcarbonyl group, an C2-C6 alkoxycarbonyl group, an C2-C8 alkylaminocarbonyl group, an C1-C6 alkyl group optionally having one or more groups selected from Group P 1 , or a C3-C6 cycloalkyl group optionally having one or more groups selected from Group P 1 ;

A 2 , Z 1 and Z 4 represent independently of each other a hydrogen atom, an amino group, an C3-C6 alkenyl group, a C3-C6 haloalkenyl group, an C3-C6 alkynyl group, a C3-C6 haloalkynyl group, an C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, an C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C3-C6 cycloalkylsulfonyl group, a C3-C6 halocycloalkylsulfonyl group, an C2-C8 alkylaminosulfonyl group, a C2-C8 haloalkylaminosulfonyl group, a C3-C9 trialkylsilyl group, an C2-C6 alkylcarbonyl group, an C2-C6 alkoxycarbonyl group, an C2-C8 alkylaminocarbonyl group, a C4-C7 cycloalkylmethyl group, an C1-C6 alkyl group optionally having one or more groups selected from Group P 1 or a C3-C6 cycloalkyl group optionally having one or more groups selected from Group P 1 ;

Z 2 and Z 3 represent independently of each other a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, a hydroxy group, a thiol group, an aldehyde group, an C2-C6 alkenyl group, a C2-C6 haloalkenyl group, an C2-C6 alkynyl group, a C2-C6 haloalkynyl group, an C1-C6 alkoxy group, a C1-C6 haloalkoxy group, an C3-C6 alkenyloxy group, a C3-C6 haloalkenyloxy group, an C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, an C3-C6 alkenylthio group, an C3-C6 alkynylthio group, a C3-C6 haloalkenylthio group, a C3-C6 haloalkynylthio group, an C1-C8 alkylamino group, a C1-C8 haloalkylamino group, an C1-C6 alkylthio group, a C1-C6 haloalkylthio group, an C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, an C1-C6 alkylsulfonyl group, a C1-C6 haloakylsulfonyl group, an C2-C8 alkylaminosulfonyl group, a pentaflurosulfanyl group, a C3-C9 trialkylsilyl group, an C2-C6 alkylcarbonyl group, an C2-C6 alkoxycarbonyl group, an aminocarbonyl group, an C2-C8 alkylaminocarbonyl group, an C1-C6 alkyl group optionally having one or more groups selected from Group P 1 or a C3-C6 cycloalkyl group optionally having one or more groups selected from Group P 1 ; or

Z 1 and Z 2 may combine each other together with the carbon atom or nitrogen atom to which they are attached to form a five-, six- or seven-membered saturated ring, said the saturated ring may optionally contain one or more oxygen atoms, nitrogen atoms or sulfur atoms as the ring-constituent atom, and the saturated ring may optionally have one or more substituents selected from Group P 1 ; or

Z 2 and Z 3 may combine each other together with the carbon atom to which they are attached to form a five-, six- or seven-membered saturated ring, said saturated ring may optionally contain one or more oxygen atoms, nitrogen atoms or sulfur atoms as the ring-constituent atom, and the saturated ring may optionally have one or more substituents selected from Group P 1 ; and

Group P 1 : a group consisting of a halogen atom, a cyano group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, an C1-C4 alkoxy group, a C1-C4 haloalkoxy group, an C1-C4 alkylthio group or a C1-C4 haloalkylthio group.

2. The tetrazolinone compound according to claim 1 wherein Q represents Q2.

3. The tetrazolinone compound according to claim 1 wherein Q represents Q3.

4. The tetrazolinone compound according to claim 1 wherein Q represents Q4.

5. The tetrazolinone compound according to claim 1 ,

wherein

R 1 represents an C1-C3 alkyl group, a halogen atom, a C1-C3 haloalkyl group, an C2-C3 alkynyl group, a C2-C3 haloalkynyl group, a C3-C5 cycloalkyl group, a C3-C5 halocycloalkyl group, an C1-C3 alkoxy group or a C1-C3 haloalkoxy group;

R 2 , R 4 , R 5 , R 7 , R 8 , R 9 and R 11 represent a hydrogen atom;

R 3 represents a hydrogen atom, a halogen atom, an C1-C3 alkyl group or a C1-C3 haloalkyl group;

R 6 represents a C3-C6 cycloalkyl group, an C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C1-C4 haloalkoxy group, an C1-C4 alkylthio group, a C1-C4 haloalkylthio group or a C3-C6 halocycloalkyl group;

R 10 represents a methyl group; and

X represents an oxygen atom.

6. The tetrazolinone compound according to claim 1 ,

wherein

Z 1 represents an C1-C6 alkyl group, a C1-C6 haloalkyl group, an C3-C6 alkynyl group, a C3-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group or a C4-C7 cycloalkylmethyl group;

Z 2 represents a hydrogen atom, a halogen atom, an C1-C6 alkyl group, a C1-C6 haloalkyl group, an C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group; alternatively,

Z 1 and Z 2 may combine each other together with the carbon atom or the nitrogen atom to which they are attached to form a five- or six-membered saturated ring; and

Z 3 represents a hydrogen atom, a halogen atom, an C1-C4 alkyl group or a C1-C4 haloalkyl group.

7. The tetrazolinone compound according to claim 1 ,

wherein

Z 1 represents an C1-C6 alkyl group;

Z 2 represents a hydrogen atom, a halogen atom, an C1-C6 alkyl group, a C1-C6 haloalkyl group, a cyano group, an C1-C6 alkoxy group or a C1-C6 alkylthio group; and

Z 3 represents a hydrogen atom, a halogen atom or an C1-C4 alkyl group.

8. The tetrazolinone compound according to claim 1 ,

wherein

Z 1 represents an C1-C3 alkyl group;

Z 2 represents a hydrogen atom, a chlorine atom, a methoxy group, an ethoxy group, a methylthio group, a cyano group, a trifluoromethyl group or an C1-C3 alkyl group; and

Z 3 represents a hydrogen atom, a halogen atom or a methyl group.

9. The tetrazolinone compound according to claim 1 ,

wherein

Z 1 represents an C1-C3 alkyl group;

Z 2 represents a hydrogen atom, a chlorine atom, a methoxy group, a methylthio group, a trifluoromethyl group a cyano group, or an C1-C3 alkyl group; and

Z 3 represents a hydrogen atom, a chlorine atom or a methyl group.

10. The tetrazolinone compound according to claim 1 ,

wherein

R 1 represents a methyl group, an ethyl group, a chlorine atom, a bromine atom or a trifluoromethyl group;

R 3 represents a hydrogen atom or a methyl group; and

R 6 represents a cyclopropyl group, an ethynyl group, a difluoromethoxy group or a methylthio group.

11. A tetrazolinone compound of a formula (2):

wherein

R 1 represents a methyl group, an ethyl group, a chlorine atom, a bromine atom, a trifluoromethyl group or a cyclopropyl group;

R 3 represents a hydrogen atom or a methyl group;

R 6 represents a cyclopropyl group, a difluoromethoxy group, an ethynyl group or a methylthio group; and

R 12 represents an C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group or a C1-C6 halocycloalkyl group.

12. The tetrazolinone compound according to claim 11 ,

wherein

R 1 represents a methyl group, an ethyl group, a chlorine atom or a bromine atom;

R 3 represents a hydrogen atom or a methyl group;

R 6 represents a cyclopropyl group; and

R 12 represents a methyl group, an ethyl group or a cyclopropyl group.

13. An agent for controlling pests comprising the tetrazolinone compound according to claim 1 .

14. A method for controlling pests comprising applying an effective amount of the tetrazolinone compound according to claim 1 to plant or soil.