Compounds having a nitrogen-containing unsaturated six-membered ring and agricultural and horticultural fungicides containing the same as active ingredients
An object of the present invention is to provide compounds represented by the formula (1) or salts thereof that are effective as agricultural and horticultural fungicides.
1. A compound represented by the formula (1), or a salt thereof:
wherein R1 represents
hydroxy,
cyano,
C1-C6 alkyl optionally substituted with at least one substituent A,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent A,
C2-C6 alkenyl optionally substituted with at least one substituent A,
C2-C6 haloalkenyl,
C2-C6 alkynyl optionally substituted with at least one substituent A,
C2-C6 haloalkynyl,
C1-C6 alkoxy optionally substituted with at least one substituent A,
C1-C6 haloalkoxy,
C3-C8 cycloalkoxy optionally substituted with at least one substituent A,
C2-C6 alkenyloxy optionally substituted with at least one substituent A,
C2-C6 haloalkenyloxy,
C3-C6 alkynyloxy optionally substituted with at least one substituent A,
C3-C6 haloalkynyloxy,
or
RaRbN— wherein Ra and Rb are independent of one another and each represent hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or a C3-C8 cycloalkyl, or Ra and Rb are taken together with the nitrogen atom to which they are bonded to form aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholyl, homopiperidinyl, or an azocanyl;
R2, R3 and R4 are independent of one another and each represent
hydrogen,
halogen,
hydroxy,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent C,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent C,
C2-C6 alkenyl optionally substituted with at least one substituent C,
C2-C6 haloalkenyl,
C2-C6 alkynyl optionally substituted with at least one substituent C,
C2-C6 haloalkynyl,
C1-C6 alkoxy optionally substituted with at least one substituent C,
C1-C6 haloalkoxy,
C3-C8 cycloalkoxy optionally substituted with at least one substituent C,
C2-C6 alkenyloxy optionally substituted with at least one substituent C,
C2-C6 haloalkenyloxy,
C3-C6 alkynyloxy optionally substituted with at least one substituent C,
C3-C6 haloalkynyloxy,
RdC(═O)— wherein Rd represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove,
RdC(═O)O— wherein Rd is the same as defined hereinabove,
Rc-L- wherein Rc represents C1-C6 alkyl or C1-C6 haloalkyl, and L represents S, SO, or SO 2 ,
Rc-SO 2 —O— wherein Rc is the same as defined hereinabove,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
ReC(═O)N(Rf)— wherein Re represents hydrogen, a C1-C6 alkyl group optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove, and Rf represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or C3-C8 cycloalkyl);
R5 represents
hydrogen,
halogen,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent A,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent A,
C2-C6 alkenyl optionally substituted with at least one substituent A,
C2-C6 haloalkenyl,
C2-C6 alkynyl optionally substituted with at least one substituent A,
C2-C6 haloalkynyl,
C1-C6 alkoxy optionally substituted with at least one substituent A,
C1-C6 haloalkoxy,
C3-C8 cycloalkoxy optionally substituted with at least one substituent A,
C2-C6 alkenyloxy optionally substituted with at least one substituent A,
C2-C6 haloalkenyloxy,
C3-C6 alkynyloxy optionally substituted with at least one substituent A,
C3-C6 haloalkynyloxy,
Rc-L- wherein Rc and L are the same as defined hereinabove,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
RgC(═O)— wherein Rg represents hydrogen, hydroxy, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove;
X represents oxygen or sulfur;
Y represents R8-C or nitrogen;
Z represents R9-C or nitrogen;
R6, R7, R8 and R9 are independent of one another and each represent hydrogen,
halogen,
hydroxy,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent C,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent C,
C2-C6 alkenyl optionally substituted with at least one substituent C,
C2-C6 haloalkenyl,
C2-C6 alkynyl optionally substituted with at least one substituent C,
C2-C6 haloalkynyl,
C1-C6 alkoxy optionally substituted with at least one substituent C,
C1-C6 haloalkoxy,
C3-C8 cycloalkoxy optionally substituted with at least one substituent C,
C2-C6 alkenyloxy optionally substituted with at least one substituent C,
C2-C6 haloalkenyloxy,
C3-C6 alkynyloxy optionally substituted with at least one substituent C,
C3-C6 haloalkynyloxy,
RdC(═O)— wherein Rd is the same as defined hereinabove,
RdC(═O)O— wherein Rd is the same as defined hereinabove,
Rc-L- wherein Rc and L are the same as defined hereinabove,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
ReC(═O)N(Rf)— wherein Re and Rf are the same as defined hereinabove, or
R6 and R7 are taken together to form C2-C6 alkylene, and, R8 and R9 represent those as defined hereinabove;
and
the at least one substituent A is at least one selected from the consisting of hydroxy, cyano, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, RaRbN— wherein Ra and Rb are the same as defined hereinabove and Rc-L- wherein Rc and L are the same as defined hereinabove;
the at least one substituent B is at least one selected from the consisting of a cyano, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkoxy; and
the at least one substituent C is at least one selected from the consisting of hydroxy, cyano, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C2-C6 alkoxyalkoxy, RaRbN— wherein Ra and Rb are the same as defined hereinabove, Rc-L- wherein Rc and L are the same as defined hereinabove, RdC(═O)— wherein Rd is the same as defined hereinabove and 3 to 6-membered ring containing 1 to 2 oxygen.
2. The compound according to claim 1 , or salt thereof, wherein
R1 represents
hydroxyl,
C1-C6 alkyl optionally substituted with at least one substituent A,
C1-C6 haloalkyl,
C2-C6 alkenyl optionally substituted with at least one substituent A,
C2-C6 haloalkenyl,
C2-C6 alkynyl optionally substituted with at least one substituent A,
C1-C6 alkoxy optionally substituted with at least one substituent A,
C1-C6 haloalkoxy,
C2-C6 alkenyloxy optionally substituted with at least one substituent A,
C3-C6 alkynyloxy optionally substituted with at least one substituent A,
or
RaRbN— wherein Ra and Rb are independent of one another and each represent a hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or C3-C8 cycloalkyl, or Ra and Rb are taken together with the nitrogen atom to which they are bonded to form an aziridinyl, an azetidinyl, pyrrolidinyl, piperidinyl, morpholyl, homopiperidinyl, or azocanyl;
R2, R3 and R4 are independent of one another and each represent
hydrogen,
halogen,
hydroxy,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent C,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent C,
C2-C6 alkenyl optionally substituted with at least one substituent C,
C2-C6 alkynyl optionally substituted with at least one substituent C,
C1-C6 alkoxy optionally substituted with at least one substituent C,
C1-C6 haloalkoxy,
C3-C8 cycloalkoxy optionally substituted with at least one substituent C,
C2-C6 alkenyloxy optionally substituted with at least one substituent C,
C3-C6 alkynyloxy optionally substituted with at least one substituent C,
RdC(═O)O— wherein Rd represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, a C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove,
Rc-L- wherein Rc represents C1-C6 alkyl or C1-C6 haloalkyl, and L represents S, SO, or SO 2 ,
Rc-SO 2 —O— wherein Rc is the same as defined hereinabove,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
ReC(═O)N(Rf)— wherein Re represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, a C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove, and Rf represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or C3-C8 cycloalkyl;
R5 represents
hydrogen,
halogen,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent A,
C1-C6 haloalkyl,
C2-C6 alkenyl optionally substituted with at least one substituent A,
C2-C6 alkynyl optionally substituted with at least one substituent A,
C1-C6 alkoxy optionally substituted with at least one substituent A,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
RgC(═O)— wherein Rg represents hydrogen, hydroxy, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove;
R6, R7, R8 and R9 are independent of one another and each represent
hydrogen,
halogen,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent C,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent C,
C2-C6 alkenyl optionally substituted with at least one substituent C,
C2-C6 alkynyl optionally substituted with at least one substituent C,
C1-C6 alkoxy optionally substituted with at least one substituent C,
C2-C6 alkenyloxy optionally substituted with at least one substituent C,
C3-C6 alkynyloxy optionally substituted with at least one substituent C,
RdC(═O)— wherein Rd is the same as defined hereinabove,
Rc-L- wherein Rc and L are the same as defined hereinabove,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
ReC(═O)N(Rf)— wherein Re and Rf are the same as defined hereinabove, or
R6 and R7 are taken together to form C2-C6 alkylene, and, R8 and R9 represent those as defined hereinabove.
3. The compound according to claim 2 , or salt thereof, wherein
R1 represents
hydroxyl,
C1-C6 alkyl optionally substituted with at least one substituent A,
C1-C6 haloalkyl,
C2-C6 alkenyl optionally substituted with at least one substituent A,
C1-C6 alkoxy optionally substituted with at least one substituent A,
C1-C6 haloalkoxy,
C2-C6 alkenyloxy optionally substituted with at least one substituent A,
C3-C6 alkynyloxy optionally substituted with at least one substituent A,
or
RaRbN— wherein Ra and Rb are independent of one another and each represent a hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or C3-C8 cycloalkyl, or Ra and Rb are taken together with the nitrogen atom to which they are bonded to form aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholyl, homopiperidinyl, or azocanyl;
R2, R3 and R4 are independent of one another and each represent
hydrogen,
halogen,
hydroxy,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent C,
C3-C8 cycloalkyl optionally substituted with at least one substituent C,
C2-C6 alkynyl optionally substituted with at least one substituent C,
C1-C6 alkoxy optionally substituted with at least one substituent C,
C1-C6 haloalkoxy,
C3-C6 alkynyloxy optionally substituted with at least one substituent C,
RdC(═O)O— wherein Rd represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are independent of one another and each represent hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or C3-C8 cycloalkyl, or Ra and Rb are taken together with the nitrogen atom to which they are bonded to form aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholyl, a homopiperidinyl, or azocanyl,
Rc-SO 2 —O— wherein Rc represents C1-C6 alkyl or C1-C6 haloalkyl, and L represents S, SO, or SO 2 ,
RaRbN— wherein Ra and Rb are the same as defined hereinabove), or
ReC(═O)N(Rf)— wherein Re represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove, and Rf represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or C3-C8 cycloalkyl;
R5 represents
hydrogen,
halogen,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent A,
C2-C6 alkenyl optionally substituted with at least one substituent A,
C1-C6 alkoxy optionally substituted with at least one substituent A,
RaRbN— wherein Ra and R b are the same as defined hereinabove, or
RgC(═O)— wherein Rg represents hydrogen, hydroxy, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove;
X represents oxygen;
when Y is R8-C, Z represents nitrogen, or, when Y is nitrogen, Z represents R9-C;
R6, R7, R8 and R9 are independent of one another and each represent
hydrogen,
halogen,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent C,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent C,
C2-C6 alkenyl optionally substituted with at least one substituent C,
C2-C6 alkynyl optionally substituted with at least one substituent C,
C1-C6 alkoxy optionally substituted with at least one substituent C,
RdC(═O)— wherein Rd is the same as defined hereinabove,
Rc-L- wherein Rc and L are the same as defined hereinabove, or
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
R6 and R7 are taken together to form C2-C6 alkylene, and R8 and R9 represent those as defined hereinabove.
4. A compound represented by the formula (2), or salt thereof:
wherein
R2, R3 and R4 are independent of one another and each represent
hydrogen,
halogen,
hydroxy,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent C,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent C,
C2-C6 alkenyl optionally substituted with at least one substituent C,
C2-C6 haloalkenyl,
C2-C6 alkynyl optionally substituted with at least one substituent C,
C2-C6 haloalkynyl,
C1-C6 alkoxy optionally substituted with at least one substituent C,
C1-C6 haloalkoxy,
C3-C8 cycloalkoxy optionally substituted with at least one substituent C,
C2-C6 alkenyloxy optionally substituted with at least one substituent C,
C2-C6 haloalkenyloxy,
C3-C6 alkynyloxy optionally substituted with at least one substituent C,
C3-C6 haloalkynyloxy,
RdC(═O)— wherein Rd represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are independent of one another and each represent hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or C3-C8 cycloalkyl, or Ra and Rb are taken together with the nitrogen atom to which they are bonded to form aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholyl, homopiperidinyl, or azocanyl,
RdC(═O)O— wherein Rd is the same as defined hereinabove,
Rc-L- wherein Rc represents C1-C6 alkyl or C1-C6 haloalkyl, and L represents S, SO, or SO 2 ,
Rc-SO 2 —O— wherein Rc is the same as defined hereinabove,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
ReC(═O)N(Rf)— wherein Re represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove, and Rf represents hydrogen, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, or C3-C8 cycloalkyl;
R5 represents
hydrogen,
halogen,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent A,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent A,
C2-C6 alkenyl optionally substituted with at least one substituent A,
C2-C6 haloalkenyl,
C2-C6 alkynyl optionally substituted with at least one substituent A,
C2-C6 haloalkynyl,
C1-C6 alkoxy optionally substituted with at least one substituent A,
C1-C6 haloalkoxy,
C3-C8 cycloalkoxy optionally substituted with at least one substituent A,
C2-C6 alkenyloxy optionally substituted with at least one substituent A,
C2-C6 haloalkenyloxy,
C3-C6 alkynyloxy optionally substituted with at least one substituent A,
C3-C6 haloalkynyloxy,
Rc-L- wherein Rc and L are the same as defined hereinabove,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
RgC(═O)— wherein Rg represents hydrogen, hydroxy, C1-C6 alkyl optionally substituted with at least one substituent B, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, or RaRbN— wherein Ra and Rb are the same as defined hereinabove;
X represents oxygen or sulfur;
Y represents R8-C or nitrogen;
Z represents R9-C or nitrogen;
R6, R7, R8 and R9 are independent of one another and each represent
hydrogen,
halogen,
hydroxy,
cyano,
nitro,
C1-C6 alkyl optionally substituted with at least one substituent C,
C1-C6 haloalkyl,
C3-C8 cycloalkyl optionally substituted with at least one substituent C,
C2-C6 alkenyl optionally substituted with at least one substituent C,
C2-C6 haloalkenyl,
C2-C6 alkynyl optionally substituted with at least one substituent C,
C2-C6 haloalkynyl,
C1-C6 alkoxy optionally substituted with at least one substituent C,
C1-C6 haloalkoxy,
C3-C8 cycloalkoxy optionally substituted with at least one substituent C,
C2-C6 alkenyloxy optionally substituted with at least one substituent C,
C2-C6 haloalkenyloxy,
C3-C6 alkynyloxy optionally substituted with at least one substituent C,
C3-C6 haloalkynyloxy,
RdC(═O)— wherein Rd is the same as defined hereinabove,
RdC(═O)O— wherein Rd is the same as defined hereinabove,
Rc-L- wherein Rc and L are the same as defined hereinabove,
RaRbN— wherein Ra and Rb are the same as defined hereinabove, or
ReC(═O)N(Rf)— wherein Re and Rf are the same as defined hereinabove, or
R6 and R7 are taken together to form C2-C6 alkylene, and, R8 and R9 represent those as defined hereinabove; and
the at least one substituent A is at least one selected from the consisting of hydroxy, cyano, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, RaRbN— wherein Ra and Rb are the same as defined hereinabove and Rc-L- wherein Rc and L are the same as defined hereinabove;
the at least one substituent B is at least one selected from the consisting of cyano, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkoxy; and
the at least one substituent C is at least one selected from the consisting of hydroxy, cyano, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C2-C6 alkoxyalkoxy, RaRbN— wherein Ra and Rb are the same as defined hereinabove, Rc-L- wherein Rc and L are the same as defined hereinabove, RdC(═O)— wherein Rd is the same as defined hereinabove and a-3 to 6-membered ring containing 1 to 2 oxygen atoms.
5. An agricultural and horticultural pest control agent comprising the compound described in claim 1 , or salt thereof, as an active ingredient.
6. An agricultural and horticultural fungicide comprising the compound described in claim 1 , or salt thereof, as an active ingredient.
7. A method for controlling a plant disease caused by a pathogen, comprising applying the agricultural and horticultural pest control agent described in claim 5 to a plant, a plant seed or soil for plant cultivation.
8. A method for controlling a plant disease caused by a pathogen, comprising applying the agricultural and horticultural fungicide described in claim 6 to a plant, a plant seed or soil for plant cultivation.
9. The method described in claim 7 , wherein the plant disease is caused by a fungal pathogen.
10. The method described in claim 8 , wherein the plant disease is caused by a fungal pathogen.