Nematicidal active compounds, their preparation methods and uses

Abstract

The present invention provides a compound represented by formula I. The compound represented by formula I has excellent nematicidal activity, thereby being capable of preparing a nematicide with high efficiency, low toxicity and good environmental compatibility.

Description

Technical Field

[0001] This invention belongs to the field of pesticides. Specifically, this invention relates to a compound with nematicidal activity, its preparation method, and its uses. Background Technology

[0002] Plant parasitic nematodes are widely distributed, diverse, and highly adaptable to various environments. They can parasitize the roots, stems, leaves, seeds, buds, and fruits of plants, causing mechanical damage and robbing the host plant of its nutrients through feeding activities. In particular, their esophageal gland secretions can lead to a series of diseases in the host plant. They can also co-infect the host plant with other pathogenic microorganisms, causing complex diseases and resulting in yield losses. Globally, plant parasitic nematodes cause agricultural losses exceeding $100 billion annually, severely hindering agricultural economic development.

[0003] There are many methods for controlling nematodes in agriculture, with chemical control currently being the primary approach. Widely used chemical nematicides are mainly highly toxic and persistent organophosphates or carbamates, such as thionylphosphonate, propargite, fenpropathrin, thiamethoxam, aldicarb, carbofuran, and others. These have low safety for humans and other non-target organisms and can cause varying degrees of pollution to soil, water sources, and agricultural products. Furthermore, due to the limited variety of these nematicides and their overuse and frequent application, serious resistance has developed, making nematode control increasingly difficult. Therefore, finding novel chemical nematicides that are highly effective, low in toxicity, and environmentally compatible has become an urgent technical problem to be solved in this field.

[0004] In summary, there is an urgent need in this field to develop new compounds with nematicidal activity. Summary of the Invention

[0005] The purpose of this invention is to develop a novel chemical nematicide that is highly efficient, low in toxicity, and environmentally compatible.

[0006] In a first aspect, the present invention provides the use of compounds of Formula I or their agrochemically acceptable salts in the preparation of nematicides.

[0007]

[0008] Where R 1Selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -CH2-Z-(C1-12 alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl) (preferably substituted or unsubstituted benzyl), or absent;

[0009] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, hydroxyl, nitro, cyano, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl), substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (wherein Z is O or NH or S), or absent;

[0010] R 6 It is hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted -CH2-Z-(C5-12 aryl or heteroaryl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl), or absent;

[0011] M 1 Selected from C, CH, S, O, or N;

[0012] M 2 M 3 M 4 Each is independently selected from: C, CH, S, O, N;

[0013] n is an integer selected from 0 to 2;

[0014] X 1 Selected from O, N, or S;

[0015] X 2 Selected from N, C, O, or S;

[0016] Y is selected from: -CH2-, -CO-, -S(O) m -,-C(O)NH-,-S(O)2NH-, oxime ether group thiocarbonyl-amino

[0017] m is 0, 1, or 2;

[0018] A is a substituted or unsubstituted C5-18 heteroaryl or heterocyclic biphenyl;

[0019] R 8 Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl), substituted or unsubstituted C1-3 alkylene-C5-12 heteroaryl or heterocyclic.

[0020] In specific embodiments, the compound shown in Formula I has the structures shown in Formulas Ia and Ib:

[0021]

[0022] Where R 1Selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy (where Z is O, NH, or S), substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O, NH, or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl) (preferably substituted or unsubstituted benzyl), or absent;

[0023] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, nitro, cyano, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl), substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (wherein Z is O or NH or S), substituted or unsubstituted C2-6 (preferably C2-4) ester;

[0024] R 6 The substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl);

[0025] M 1 Selected from C or N;

[0026] M 2 M 3 M 4 Each is independently selected from: C, S, O, N;

[0027] X 1 Selected from O, N, or S;

[0028] X 2 Selected from N, C, O, or S;

[0029] Y is selected from: -CH2-, -CO-, -S(O) m -、-C(O)NH-、-S(O)2NH-、oxime ether group

[0030] m is 0, 1, or 2;

[0031] A is a substituted or unsubstituted C5-18 heteroaryl group;

[0032] R 8 Selected from hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl).

[0033] In specific embodiments, the compound shown in Formula I has the structures shown in Formulas Ic to Ig:

[0034]

[0035] where R 1 Selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy (where Z is O, NH, or S), substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O, NH, or S), substituted or unsubstituted C5-12 aryl or heteroaryl, or absent;

[0036] R 2 R 3 R 4 R 5Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, nitro, cyano, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy or substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (wherein Z is O or NH or S), or absent;

[0037] R 6 It is hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2- (C5-12 aryl or heteroaryl), or absent;

[0038] M 1 Selected from C or N;

[0039] M 2 M 3 M 4 Each can be independently selected from C, S, O, or N;

[0040] X 1 Selected from N, O, or S;

[0041] X 2 Selected from N or C;

[0042] Y is selected from: -CH2-, -CO-, -S(O) m -、-C(O)NH-、-S(O)2NH-、oxime ether group

[0043] m is 0, 1, or 2;

[0044] A is a substituted or unsubstituted C5-18 heteroaryl group;

[0045] R 8Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl).

[0046] In a specific implementation, R 1 Selected from: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy (where Z is O or NH or S), substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl;

[0047] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, cyano, trifluoromethyl, trifluoromethoxy, nitro, methyl, methoxy, substituted or unsubstituted C2-4 ester group, substituted or unsubstituted amide group, substituted or unsubstituted C5-12 aryl or heteroaryl or substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (where Z is O or NH or S);

[0048] R 6 Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted C5-12 aryl or heteroaryl;

[0049] Y is selected from: -CH2-, -S-, -CONH-, -CO-, -CS-, -S(O)2-, oxime ether group

[0050] R 8Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl).

[0051] In a specific implementation, R 8 Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl, substituted or unsubstituted -CH2- (C5-12 aryl or heteroaryl).

[0052] In a specific implementation, R 8 Selected from:

[0053] hydrogen,

[0054] In specific embodiments, the compound shown in Formula I has the structures shown in Formulas Ih to Ij:

[0055]

[0056] Where R 1 R 2 R 3 R 4 R 5 R 6 M 1 M 3 X 1 X 2 As stated above, and A.

[0057] In a specific embodiment, the compound shown in Formula I has the structure shown in Formula Ik:

[0058]

[0059] Where R 1Selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy (where Z is O or NH or S), substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl;

[0060] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, nitro, cyano, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (wherein Z is O or NH or S);

[0061] R 6 Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2- (C5-12 aryl or heteroaryl);

[0062] M 1 Selected from C or N;

[0063] X 1 Selected from N, O, or S;

[0064] X 2 Selected from N or C;

[0065] A is a substituted or unsubstituted C5-12 heteroaryl group.

[0066] In specific embodiments, the compound represented by formula Ik has the structures represented by formulas Il to q:

[0067]

[0068] Where R 1 R 2 R 3 R 4 R 5 R 6 As stated above, and A.

[0069] In a specific embodiment, A is selected from the following groups, whether substituted or unsubstituted:

[0070]

[0071] R 9 Selected from substituted or unsubstituted C2-4 ester groups, substituted or unsubstituted amide groups, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy groups, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl groups, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl groups, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl groups, and substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl).

[0072] In a specific implementation, A is selected from:

[0073]

[0074] More preferably, A is selected from:

[0075]

[0076] In a preferred embodiment, the substituent group of A is hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, methyl, or methoxy.

[0077] In specific embodiments, the compounds are: I-1, I-2, I-3, I-5, I-20, I-21, I-24, I-25, I-28, I-29, I-32, I-33, I-44, I-96, I-97, I-103, I-111, I-112, I-114, I-115, I-128;

[0078] Preferably, the compound is: I-1, I-2, I-3, I-5, I-20, I-21, I-24, I-25, I-28, I-29, I-32, I-33, I-44.

[0079] In a second aspect, the present invention provides a nematicide or nematicidal pesticide composition comprising the compound described in the first aspect or a pesticide-acceptable salt thereof and optionally a pesticide-acceptable excipient.

[0080] In a third aspect, the present invention provides a compound of formula I or a pesticide-acceptable salt thereof.

[0081]

[0082] where R 1 Selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -CH2-Z-(C1-12 alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl) (preferably substituted or unsubstituted benzyl), or absent;

[0083] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, hydroxyl, nitro, cyano, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl), substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (wherein Z is O or NH or S), or absent;

[0084] R 6It is hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted -CH2-Z-(C5-12 aryl or heteroaryl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl), or absent;

[0085] M 1 Selected from C, CH, S, O, or N;

[0086] M 2 M 3 M 4 Each is independently selected from: C, CH, S, O, N;

[0087] n is an integer selected from 0 to 2;

[0088] X 1 Selected from O, N, or S;

[0089] X 2 Selected from N, C, O, or S;

[0090] Y is selected from: -CH2-, -CO-, -S(O) m -,-C(O)NH-,-S(O)2NH-, oxime ether group thiocarbonyl-amino

[0091] m is 0, 1, or 2;

[0092] A is a substituted or unsubstituted C5-18 heteroaryl or heterocyclic biphenyl;

[0093] R 8Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl), substituted or unsubstituted C1-3 alkylene-C5-12 heteroaryl or heterocyclic.

[0094] In specific embodiments, the compound shown in Formula I has the structures shown in Formulas Ia and Ib:

[0095]

[0096] where R 1 Selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy (where Z is O, NH, or S), substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O, NH, or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl) (preferably substituted or unsubstituted benzyl), or absent;

[0097] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, nitro, cyano, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl), substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (wherein Z is O or NH or S), substituted or unsubstituted C2-6 (preferably C2-4) ester;

[0098] R 6 The substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl);

[0099] M 1 Selected from C or N;

[0100] M 2 M 3 M 4 Each is independently selected from: C, S, O, N;

[0101] X 1 Selected from O, N, or S;

[0102] X 2 Selected from N, C, O, or S;

[0103] Y is selected from: -CH2-, -CO-, -S(O) m -、-C(O)NH-、-S(O)2NH-、oxime ether group

[0104] m is 0, 1, or 2;

[0105] A is a substituted or unsubstituted C5-18 heteroaryl group;

[0106] R 8 Selected from hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl).

[0107] In specific embodiments, the compound shown in Formula I has the structures shown in Formulas Ic to Ig:

[0108]

[0109] where R 1 Selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy (where Z is O, NH, or S), substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O, NH, or S), substituted or unsubstituted C5-12 aryl or heteroaryl, or absent;

[0110] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, nitro, cyano, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy or substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (wherein Z is O or NH or S), or absent;

[0111] R 6 It is hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2- (C5-12 aryl or heteroaryl), or absent;

[0112] M 1 Selected from C or N;

[0113] M 2 M 3 M 4 Each can be independently selected from C, S, O, or N;

[0114] X 1 Selected from N, O, or S;

[0115] X 2 Selected from N or C;

[0116] Y is selected from: -CH2-, -CO-, -S(O) m -、-C(O)NH-、-S(O)2NH-、oxime ether group

[0117] m is 0, 1, or 2;

[0118] A is a substituted or unsubstituted C5-18 heteroaryl group;

[0119] R 8 Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl).

[0120] In a specific implementation, R 1 Selected from: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy (where Z is O or NH or S), substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl;

[0121] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, cyano, trifluoromethyl, trifluoromethoxy, nitro, methyl, methoxy, substituted or unsubstituted C2-4 ester group, substituted or unsubstituted amide group, substituted or unsubstituted C5-12 aryl or heteroaryl or substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (where Z is O or NH or S);

[0122] R 6Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted C5-12 aryl or heteroaryl;

[0123] Y is selected from: -CH2-, -S-, -CONH-, -CO-, -CS-, -S(O)2-, oxime ether group

[0124] R 8 Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl).

[0125] In a specific implementation, R 8 Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl, substituted or unsubstituted -CH2- (C5-12 aryl or heteroaryl).

[0126] In a specific implementation, R 8 Selected from: hydrogen,

[0127] In specific embodiments, the compound shown in Formula I has the structures shown in Formulas Ih to Ij:

[0128]

[0129] Where R 1 R 2 R 3 R 4 R 5 R 6 M 1 M 3 X 1 X 2 As stated above, and A.

[0130] In a specific embodiment, the compound shown in Formula I has the structure shown in Formula Ik:

[0131]

[0132] Where R 1 Selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted amino, substituted or unsubstituted amide, substituted or unsubstituted sulfonamide, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted -Z-C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy (where Z is O or NH or S), substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl;

[0133] R 2 R 3 R 4 R 5 Each is independently selected from: hydrogen, halogen, substituted or unsubstituted amino, nitro, cyano, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (wherein Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -Z-(C5-12 aryl or heteroaryl) (wherein Z is O or NH or S);

[0134] R 6 Selected from: hydrogen, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl, substituted or unsubstituted C5-12 aryl or heteroaryl, substituted or unsubstituted -CH2- (C5-12 aryl or heteroaryl);

[0135] M 1 Selected from C or N;

[0136] X 1 Selected from N, O, or S;

[0137] X 2 Selected from N or C;

[0138] A is a substituted or unsubstituted C5-12 heteroaryl group.

[0139] In specific embodiments, the compound represented by formula Ik has the structures represented by formulas Il to q:

[0140]

[0141] Where R 1 R 2 R 3 R 4 R 5 R 6 As stated above, and A.

[0142] In a specific embodiment, A is selected from the following groups, whether substituted or unsubstituted:

[0143]

[0144] R 9 Selected from substituted or unsubstituted C2-4 ester groups, substituted or unsubstituted amide groups, substituted or unsubstituted C1-12 (preferably C1-6, more preferably C1-4) alkyl or alkoxy groups, substituted or unsubstituted C3-12 (preferably C3-6) cycloalkyl groups, substituted or unsubstituted C2-12 (preferably C2-6, more preferably C2-4) alkenyl or alkynyl groups, substituted or unsubstituted -CH2-Z-(C1-12 (preferably C1-6, more preferably C1-4) alkyl or C3-12 (preferably C3-6) cycloalkyl) (where Z is O or NH or S), substituted or unsubstituted C5-12 aryl or heteroaryl groups, and substituted or unsubstituted -CH2-(C5-12 aryl or heteroaryl).

[0145] In a specific implementation, A is selected from:

[0146]

[0147] More preferably, A is selected from:

[0148]

[0149] In a preferred embodiment, the substituent group of A is hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, methyl, or methoxy.

[0150] In specific embodiments, the compounds are: I-20, I-24, I-28, I-32, and I-44.

[0151] In a fourth aspect, the present invention provides a method for killing nematodes, comprising administering an effective amount of the nematicide or nematicide pesticide composition of the second aspect or the compound of the third aspect or a pesticide-acceptable salt thereof to a plant to which nematodes need to be killed.

[0152] In a preferred embodiment, the nematodes include, but are not limited to: root-knot nematodes, such as peanut root-knot nematode (Meloidogyne arenaria), chitwoodi root-knot nematode (Meloidogyne chitwoodi), exigua root-knot nematode (Meloidogyne exigua), northern root-knot nematode (Meloidogyne hapla), southern root-knot nematode (Meloidogyne incognita), Javan root-knot nematode (Meloidogyne javanica), and other genus *Meloidogyne*; cyst nematodes, such as potato golden nematode (Globodera rostochiensis), potato white nematode (Globoderapallida), tobacco cyst nematode (Globodera tabacum), and other genus *Globodera*; and heterodermal nematodes, such as cereal cyst nematode (Heterodera avenae) and soybean cyst nematode (Heterodera). *Heterodera glycines*, *Heterodera schachtii*, *Heterodera trifolii*, and other *Heterodera* nematodes; seed gall nematodes, such as *Anguina funesta*, *Anguina tritici*, and other *Anguina* nematodes; stem and leaf bud nematodes, such as *Aphelenchoides besseyi*, *Aphelenchoides fragariae*, *Aphelenchoides ritzemabosi*, and other *Aphelenchoides* nematodes; stinging nematodes, such as *Belonolaimus longicaudatus* and other *Belonolaimus* nematodes; pine nematodes, such as *Bursaphelenchus*. xylophilus and other genus of umbrella-shaped nematodes (Bursaphelenchus); annular nematodes, such as Criconema, Criconemella, Criconemoides and Mesocriconema; bulb nematodes, such as Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus, and other genus of stem nematodes (Ditylenchus);Trypanosomes, such as those in the genus *Dolichodorus*; spiral nematodes, such as *Helicotylenchus dihystera*, *Helicotylenchus multicintus*, and other genera of *Helicotylenchus*; sheath nematodes, such as those in the genera *Hemicycliophora* and *Hemicriconemoides*; crown nematodes, such as *Hoploaimus columbus* and other genera of *Hoploaimus*; pseudo-root-nodule nematodes, such as *Nacobbus aberrans* and other genera of *Nacobbus*; needle nematodes, such as *Longidorus*. *Paratylenchus* and other long-needle nematodes; *Paratylenchus* nematodes; root-rot nematodes, such as *Pratylenchus brachyurus*, *Pratylenchus coffee*, *Pratylenchus zeae*, *Pratylenchus penetrans*, and other short-bodied nematodes; perforating nematodes, such as *Radopholus similis* and other perforating nematodes; kidney-shaped nematodes, such as *Rotylenchus robustus* and other kidney-shaped nematodes; and residual root nematodes, such as *Trichodorus*. *Tylenchorhynchus* and other spiky nematodes; dwarf nematodes, such as *Tylenchorhynchus claytoni*, *Tylenchorhynchus dubius*, and other dwarf nematodes; citrus nematodes, such as *Tylenchulus semipenetrans* and other small pad nematodes; xiphine nematodes, such as *Xiphinema americanum*, *Xiphinema index*, *Xiphinema diversicaudatum*, and other xiphinema species.

[0153] Preferably, the nematode is the southern root-knot nematode (Meloidogyne incognita) and the pine wood nematode (Bursaphelenchus xylophilus).

[0154] In a preferred embodiment, the plants include, but are not limited to: grain crops such as peanuts, rice, soybeans, sorghum, and wheat; vegetables such as cucumbers, tomatoes, spinach, cabbage, and beets; trees such as banana trees, poplar trees, pine trees, cypress trees, and coconut trees; as well as tobacco, potatoes, and citrus fruits.

[0155] It should be understood that, within the scope of this invention, the above-described technical features of this invention and the technical features specifically described below (such as in the embodiments) can be combined with each other to form new or preferred technical solutions. Due to space limitations, they will not be described in detail here. Detailed Implementation

[0156] Through extensive and in-depth research, the inventors unexpectedly discovered a series of novel chemical nematicides that are highly efficient, low in toxicity, and environmentally compatible, thus laying a completely new material foundation for the development of nematicides. Based on this, the present invention was completed.

[0157] Group definition

[0158] The term "C 1-6 "Alkyl" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, or similar groups.

[0159] The term "C 2-6 "Alkenyl" refers to alkenyl groups with 2-6 carbon atoms, either straight or branched, such as vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, or similar groups.

[0160] The term "C 2-6 "Alynyl" refers to a straight-chain or branched alkynyl group with 2-6 carbon atoms, such as ethynyl, propynyl, or similar groups.

[0161] The term "C 3-7 "Cycloalkyl" refers to cyclic alkyl groups having 3 to 7 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or similar groups.

[0162] The term "C 5-7 "Cycloalkenyl" refers to a cyclic alkenyl group having 5-7 carbon atoms and one or more double bonds, such as cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, or similar groups.

[0163] As used in this article, the term "C"1-4 "Alkoxy" refers to a straight-chain or branched alkoxy group having 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, or similar groups.

[0164] The term "halogen" refers to fluorine, chlorine, bromine, or iodine. The term "halogenated" refers to a group substituted with one or more of the same or different halogen atoms, such as trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl, or similar groups.

[0165] The term "ring" or "cyclic system" refers to carbon rings or heterocycles.

[0166] The term "heterocycle" refers to a ring in which at least one atom forming the skeleton of the heterocycle is not carbon, but nitrogen, oxygen, or sulfur. Typically, a heterocycle contains no more than four nitrogen atoms, no more than two oxygen atoms, and / or no more than two sulfur atoms. Unless otherwise specified, a heterocycle can be a saturated, partially unsaturated, or fully unsaturated ring.

[0167] The term "ring system" refers to a fused ring consisting of two or more rings joined together.

[0168] As used herein, the term "5- or 6-membered heterocyclic group" refers to a five- or six-membered ring containing one or more heteroatoms selected from nitrogen, oxygen, or sulfur, such as pyridinyl, thiazolyl, isothiazolyl, thiophene, furanyl, pyrroloyl, pyrazolyl, pyrimidinyl, tetrahydrofuranyl, 4,5-dihydrothiazolyl-2-yl, 2-cyanoimino-4-oxo-1,3-thiazolyl-3-yl, 2-cyanoimino -4-O-1,3-thiazinyl-3-yl, oxazolyl, isoxazolyl, 1H-tetrazoleyl, 1H-1,2,3-triazolyl, 4H-1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl or tetrazolyl, etc.

[0169] The term "heterocyclic ring system" refers to a ring system in which at least one ring is a heterocyclic ring.

[0170] The term "hybrid aromatic ring system" refers to a system in which at least one ring is an aromatic ring.

[0171] As used herein, the terms “8- to 12-membered heteroaromatic bicyclic ring system” or “8- to 14-membered heteroaromatic bicyclic or tricyclic ring system” may be selected from the following group: benzofuran, benzo[b]thiophene, indole, quinoline, isoquinoline, 1H-indazole, 1H-benzo[d]imidazole, benzo[d]thiazole, benzo[d]oxazole, benzo[d]isoxazole, benzo[d][1,2,3]thiadiazole, 2,3-dihydroimidazo[1,2-a]pyridine, quinazoline, quinoxaline, cyclophosphine, phthalazine, 1,8-naphthidine, 4,5,6,7 -Tetrahydrobenzo[b]thiophene, benzo[b]thiophene-1,1-dioxane, 8H-indo[2,1-b]thiophene, 7,8-dihydro-6H-cyclopentane[4,5]thiophene[2,3-d]pyrimidine, 3,5,6,7-tetrahydro-4H-cyclopentane[4,5]thiophene[2,3-d]pyrimidine-4-one, spiro[indoline-3,2'-[1,3]dioxane]-2-one, spiro[indoline-3,2'-[1,3]dioxane]-2-one or indoline-2,3-dione, etc.

[0172] The term "alkyl" refers to a group formed by removing one hydrogen atom from an alkane molecule; the term "alkylene" refers to a group formed by removing two hydrogen atoms from an alkane molecule. Similarly, the definitions of "alkenylene," "ynyneinene," "cycloalkylene," "cycloalkenylene," "phenylene," "naphthylene," "heterocyclic," or "heteroaromatic bicyclic or tricyclic ring system" are similar.

[0173] Unless otherwise specified as "substituted or unsubstituted", the functional groups described in this invention may be substituted by substituents selected from the group consisting of: halogen, cyano, nitro, C. 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 alkenyl, C 2-6 Haloalkenyl, C 2-6 alkynyl group, C 2-6 Halogenated alkynyl, hydroxyl, hydroxyl C 1-4 Alkyl, OR 3 NR 3 R 4 C(O)R 3 C(O)OR 3 C(O)NR 3 R 4 SR 3 S(O) m R 5 、S(O)2NR 3 R 4 OC(O)R 5 OC(O)NR 3 R 4 OS(O)2R 5 OS(O)2NR3 R 4 、N(R 6 )C(O)R 5 、N(R 6 )C(O)NR 3 R 4 、N(R 6 )S(O)2R 5 or N(R) 6 )S(O)2NR 3 R 4 etc., wherein the R 3 R 4 R 5 R 6 The definition is the same as before, where m is 1 or 2.

[0174] Inert solvents refer to various solvents that do not react with the raw materials, including various straight-chain, branched or cyclic alcohols, ethers or ketones, haloalkanes, 1,4-dioxane, acetonitrile, tetrahydrofuran, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), etc.

[0175] The compounds of this invention may contain one or more asymmetric centers and thus appear as racemates, racemic mixtures, single enantiomers, diastereomers, and single diastereomers. The asymmetric centers that can exist depend on the nature of the various substituents on the molecule. Each such asymmetric center will independently produce two optical isomers, and all possible optical isomers, diastereomer mixtures, and pure or partially pure compounds are included within the scope of this invention. This invention encompasses all isomeric forms of the compounds.

[0176] Nematode-killing activity of the active substance of this invention

[0177] The terms "active substance of the present invention" or "active compound of the present invention" refer to compounds with the structure shown in general formula (I), their optical isomers, cis-trans isomers, or pesticide-acceptable salts. Their N- and S-containing heterocyclic structures exhibit significant nematicidal activity, with a broad nematicidal spectrum and strong stability.

[0178] The term "pesticide-acceptable salt" means that the anion of the salt is known and acceptable in forming a nematicide-pesticide-pesticide-acceptable salt. Preferably, the salt is water-soluble. Suitable acid addition salts formed from compounds of formula (I) include salts formed from inorganic acids, such as hydrochlorides, phosphates, sulfates, and nitrates; and salts formed from organic acids, such as acetates, benzoates, etc.

[0179] The active substance of this invention can be used to control and eliminate a wide range of parasitic nematodes in agricultural and forestry plants. In this specification, "nematicide" is a general term for substances that have the effect of controlling all plant parasitic nematodes mentioned herein.

[0180] Examples of plant-parasitic nematodes include, but are not limited to: root-knot nematodes, such as the peanut root-knot nematode (Meloidogynearenaria), the chitwood nematode (Meloidogyne chitwoodi), the short root-knot nematode (Meloidogyneexigua), the northern root-knot nematode (Meloidogyne hapla), the southern root-knot nematode (Meloidogyne incognita), the Javan root-knot nematode (Meloidogyne javanica), and other genus *Meloidogyne*; cyst nematodes, such as the potato golden nematode (Globodera rostochiensis), the potato white nematode (Globodera pallida), the tobacco cyst nematode (Globodera tabacum), and other genus *Globodera*; and heterodermal nematodes, such as the cereal cyst nematode (Heterodera avenae) and the soybean cyst nematode (Heterodera... *Heteroderaschachtii*, *Heterodera trifolii*, and other *Heterodera* nematodes; seed nematodes, such as *Anguina funesta*, *Anguina tritici*, and other *Anguina* nematodes; stem and leaf bud nematodes, such as *Aphelenchoides besseyi*, *Aphelenchoides fragariae*, *Aphelenchoides ritzemabosi*, and other *Aphelenchoides* nematodes; stinging nematodes, such as *Belonolaimus longicaudatus* and other *Belonolaimus* nematodes; pine nematodes, such as *Bursaphelenchus*. xylophilus and other genus of umbrella-shaped nematodes (Bursaphelenchus); annular nematodes, such as Criconema, Criconemella, Criconemoides and Mesocriconema; bulb nematodes, such as Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus, and other genus of stem nematodes (Ditylenchus);Trypanosomes, such as those in the genus *Dolichodorus*; spiral nematodes, such as *Helicotylenchus dihystera*, *Helicotylenchus multicintus*, and other genera of *Helicotylenchus*; sheath nematodes, such as those in the genera *Hemicycliophora* and *Hemicriconemoides*; crown nematodes, such as *Hoploaimus columbus* and other genera of *Hoploaimus*; pseudo-root-nodule nematodes, such as *Nacobbus aberrans* and other genera of *Nacobbus*; needle nematodes, such as *Longidorus*. *Paratylenchus* and other long-needle nematodes; *Paratylenchus* nematodes; root-rot nematodes, such as *Pratylenchus brachyurus*, *Pratylenchus coffee*, *Pratylenchus zeae*, *Pratylenchus penetrans*, and other short-bodied nematodes; perforating nematodes, such as *Radopholus similis* and other perforating nematodes; kidney-shaped nematodes, such as *Rotylenchus robustus* and other kidney-shaped nematodes; and residual root nematodes, such as *Trichodorus*. *Tylenchorhynchus* and other spiky nematodes; dwarf nematodes, such as *Tylenchorhynchus claytoni*, *Tylenchorhynchus dubius*, and other dwarf nematodes; citrus nematodes, such as *Tylenchulus semiipenetrans* and other small pad-splitter nematodes; xiphine nematodes, such as *Xiphinema americanum*, *Xiphinema index*, *Xiphinema diversicaudatum*, and other xiphine nematodes.

[0181] The compounds involved in this invention have particularly good control effects against southern root-knot nematode (Meloidogyne incognita) and pine wood nematode (Bursaphelenchus xylophilus).

[0182] Nematicide Composition Containing the Active Substance of the Present Invention

[0183] The active substances of the present invention can be prepared into nematicide compositions using conventional methods. These active compounds can be formulated into conventional formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with the active substances, microcapsules in polymers, seed coating compounds, and formulations for use with combustion devices, such as fumigation cylinders, fumigation canisters and fumigation pans, as well as ULV cold mist and warm mist formulations.

[0184] These formulations can be produced using known methods, such as mixing the active compound with a expander, which can be a liquid, liquefied gas, or solid diluent or carrier, and can be any type of surfactant, i.e., emulsifier and / or dispersant and / or foaming agent. For example, when water is used as the expander, organic solvents can also be used as adjuvants.

[0185] Liquid solvents are generally suitable as diluents or carriers, such as: aromatic hydrocarbons, such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride, or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions; alcohols, such as ethanol or ethylene glycol and their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; or less commonly used polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.

[0186] A liquefied gas diluent or carrier refers to a liquid that will become a gas at normal temperature and pressure, such as aerosol propellants, halogenated hydrocarbons, and butane, propane, nitrogen, and carbon dioxide.

[0187] Solid carriers can be ground natural minerals such as kaolin, clay, talc, quartz, activated clay, montmorillonite, or diatomaceous earth; and ground synthetic minerals such as highly dispersed silica, alumina, and silicates. Solid carriers for granulation are crushed and graded natural zircon, such as calcite, marble, pumice, sepiolite, and dolomite, as well as granules synthesized from inorganic and organic coarse powders, and granules of organic materials such as sawdust, coconut husks, corncobs, and tobacco stalks.

[0188] Nonionic and anionic emulsifiers can be used as emulsifiers and / or foam forming agents. Examples include polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, such as alkylaryl polyethylene glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, and albumin hydrolysates. Dispersants include lignin sulfite waste and methylcellulose.

[0189] Binders, such as carboxymethyl cellulose, and natural and synthetic polymers in the form of powders, granules, or emulsions, such as gum arabic, polyvinyl alcohol, and polyvinyl acetate, can be used in the formulation.

[0190] Coloring agents such as inorganic dyes, such as iron oxide, cobalt oxide and Prussian blue; organic dyes, such as azo dyes or metal phthalocyanine dyes; and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, aluminum and zinc, can be used.

[0191] These active compounds of the present invention can be mixed with other active compounds and exist in their commercial formulations or in dosage forms prepared from these formulations. These other active compounds are insecticides, fungicides, herbicides, growth controllers, etc. Insecticides include, for example, phosphate esters, carbamates, chlorinated hydrocarbons, pyrethroids, neonicotinoids, diamides, and substances produced by microorganisms, such as abamectin. Fungicides include methoxyacrylates, amides, triazoles, succinate dehydrogenase inhibitors, etc.

[0192] Furthermore, these active compounds of the present invention can also be mixed with synergists in their commercial formulations or in dosage forms prepared from these formulations. These synergists are compounds that enhance the activity of the active compounds. Since the active compounds themselves are active, it is not necessary to add synergists.

[0193] These formulations typically contain 0.001-99.99% by weight, preferably 0.01-99.9% by weight, and more preferably 0.05-90% by weight, of the active compound of the present invention, comprising the total weight of the nematicide composition. The concentration of the active compound in commercial formulations or application formulations can vary over a wide range. The concentration of the active compound in application formulations can range from 0.0000001-100% (g / v), preferably between 0.0001 and 1% (g / v).

[0194] Preparation method of the compound of the present invention

[0195] The compounds represented by the general formula of this invention can be prepared by the following method; however, the conditions of this method, such as reactants, solvents, bases, amounts of compounds used, reaction temperatures, and reaction times, are not limited to those explained below. The compounds of this invention can also be conveniently prepared by optionally combining various synthetic methods described in this specification or known in the art, such combinations being readily performed by those skilled in the art. Reagents can be commercially available if feasible.

[0196] Typical embodiments of the compounds of this invention can be synthesized using the general reaction scheme described below. It will be apparent from the description given herein that the general scheme can be modified by substituting other materials having similar structures to obtain correspondingly different products. The synthetic methods can be tailored to provide large-scale production. The starting materials can be obtained commercially or synthesized using publicly available methods. In the examples given herein, the characteristics of the final products generally make the characteristics of the necessary starting materials readily apparent through simple testing steps.

[0197] Synthesis reaction parameters

[0198] The compounds of the present invention can be prepared from readily available starting materials using, for example, the general methods and procedures described below. It will be appreciated that other method conditions may also be used, unless otherwise indicated, given typical or optimized method conditions (i.e., reaction temperature, time, molar ratio of reactants, solvent, catalyst, pressure, etc.). Optimal reaction conditions may vary depending on the specific reactants or solvents used, but such conditions can be determined by those skilled in the art through conventional optimization procedures.

[0199] The starting materials used in the following reactions are typically known compounds, or can be prepared by known steps or by obvious modifications thereof. For example, many starting materials are available from commercial suppliers, while others can be prepared by steps described in the text of the standard references or by obvious modifications.

[0200] In the preparation method of the present invention, each reaction is typically carried out in an inert solvent at a reaction temperature of -20 to 120°C (preferably -10 to 0°C, 20 to 30°C, or 80 to 100°C). The reaction time is typically 2 to 24 hours, preferably 4 to 18 hours, and the reaction time can be appropriately extended according to the needs of the reaction. The specific reaction time is determined according to the degree of reaction.

[0201] The bases used in the reaction include (but are not limited to): triethylamine, diisopropylethylamine, diethylamine, piperidine, piperazine, morpholine, N-methylmorpholine, triethylenediamine (DABCO), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, or combinations thereof.

[0202] Advantages of the present invention:

[0203] 1. This invention provides a series of compounds with novel structures and nematicidal activity, thus laying a new material basis for the development of nematicides;

[0204] 2. The compounds of the present invention exhibit good in vivo activity against root-knot nematodes and pine wood nematodes, and have broad-spectrum properties.

[0205] The technical solution of the present invention will be further described below with reference to specific implementation examples. However, the following embodiments do not constitute a limitation of the present invention. All application methods based on the principles and technical means of the present invention are within the scope of the present invention.

[0206] Unless otherwise specified, experimental methods in the following examples are generally performed under standard conditions or as recommended by the manufacturer. Percentages and parts are by weight unless otherwise stated.

[0207] Example 1: Synthesis of (1H-indol-2-yl)(thiophen-2-yl) methyl ketone, i.e., compound I-3

[0208] 1.612 g (10 mmol) of benzopyrrole-2-carboxylic acid was slowly added dropwise to a 100 mL toluene solution containing 1.756 g (10 mmol) of 2-chloro-4,6-dimethoxy-1,3,5-triazine and 1.011 g (10 mmol) of N-methylmorpholine. The reaction was carried out at room temperature, and the reaction was monitored by TLC. After the reaction was completed, 1.535 g (12 mmol) of 2-thiopheneboronic acid, 0.140 g (0.2 mmol) of bis(triphenylphosphine)palladium dichloride and 8.490 g (40 mmol) of potassium phosphate were added to the reaction system. The mixture was heated to reflux under argon protection, and the reaction was monitored by TLC. After the reaction was completed, the solvent was removed by vacuum distillation, and 100 mL of water was added to the residue. The mixture was extracted with dichloromethane (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 1.864 g of yellow solid, with a yield of 84%.

[0209] 1H NMR (400MHz, DMSO-d6) δ11.96(s,1H),8.15(dd,J=3.8,1.0Hz,1H),8.09(dd,J=5.0,1.0Hz ,1H),7.75(d,J=8.0Hz,1H),7.55–7.48(m,2H),7.36–7.29(m,2H),7.12(t,J=7.4Hz,1H). 13 C NMR (101MHz, DMSO) δ 177.28, 142.50, 137.81, 134.31, 133.86, 133.35, 128.72, 127.09, 125.59, 122.79, 120.39, 112.66, 110.09. HRMS (EI+): m / z Calculated values: C 13 Measured value of H9NOS227.0405: 227.0407.

[0210] Example 2: Synthesis of Compound I-99

[0211]

[0212] Using suitable starting materials, compound I-99 was synthesized using a similar procedure to that used in the synthesis of compound I-3.

[0213] 1 H NMR(400MHz,Chloroform-d)δ12.01(s,1H),8.77(s,1H),8.23(d,J=3.2Hz,1H),7.82(d,J=7.8Hz ,1H),7.79(d,J=2.8Hz,1H),7.64(d,J=8.2Hz,1H),7.54(d,J=8.2Hz,1H),7.33(t,J=7.4Hz,1H). 13 C NMR (101MHz, CDCl3) δ 173.66, 164.32, 153.21, 150.64, 145.43, 128.91, 127.55, 126.27, 123.12, 122.43, 119.22, 113.21. HRMS (EI+): m / z Calculated values: C 12 H8N2OS 228.0357, measured value: 228.0356.

[0214] Example 3 Synthesis of Compound I-92

[0215]

[0216] Using suitable starting materials, compound I-92 was synthesized using a similar procedure to that used in the synthesis of compound I-3.

[0217] 1 H NMR(400MHz,Chloroform-d)δ9.21(s,1H),8.76(s,1H),8.06(d,J=8.0Hz,1H),7.95(d,J=4.0Hz,1H),7.45-7.42(m,1H),7.20(dd,J=8.0,4.0Hz,1H).. 13 CNMR (101MHz, CDCl3) δ 184.12, 157.23, 154.42, 149.41, 147.91, 146.12, 136.62, 133.44, 122.31, 119.89, 116.51. HRMS (EI+): m / z Calculated value: C 11 H6N2O2S 230.0150, measured value: 230.0151.

[0218] Example 5 Synthesis of Compound I-7

[0219]

[0220] Using suitable starting materials, compound I-7 was synthesized using a similar procedure to that used in the synthesis of compound I-3.

[0221] 1 H NMR (400MHz, Chloroform-d) δ7.93(dd,J=3.8,1.0Hz,1H),7.88(d,J=4.0Hz,1H),7.73–7.67(m,2H),7.50–7.34(m,4H),7.20(dd,J=4.8,4.0Hz,1H). 13 C NMR (101MHz, CDCl3) δ178.50,152.62,142.86,141.62,140.25,133.28,132.88,129.15,129.07,127.93,126.33,123.86.HRMS(EI+):m / z Calc.Mass:C 12 H7NO2S229.0198, Mass:229.0197

[0222] Example 5: Synthesis of Compound I-93

[0223]

[0224] Using suitable starting materials, compound I-93 was synthesized using a similar procedure to that used in the synthesis of compound I-3.

[0225] 1 H NMR (400MHz, DMSO-d6) δ11.51(s,1H),7.76(s,1H),7.79(dd,J=4.8,1.2Hz,1H),7.58(d,J=1.0Hz,1H),7.36(d,J=4.6Hz,1H),6.69(s,1H),2.13(s,3H). 13 C NMR (101MHz, DMSO) δ 184.51, 159.08, 154.21, 148.51, 137.32, 129.52, 128.15, 123.21, 116.15, 101.13, 98.36, 11.31; HRMS (EI+): m / z calculated values: C 14 H 11 NO2 225.0790, measured value: 225.0788.

[0226] Example 6 Synthesis of Compound I-14

[0227]

[0228] Using suitable starting materials, compound I-14 was synthesized using a similar procedure to that used in the synthesis of compound I-3.

[0229] 1 H NMR (400MHz, Chloroform-d) δ8.03–7.96(m,1H),7.92–7.83(m,2H),7.79(dd,J=4.8,1.2Hz,1H),7.59–7.51(m,2H),7.19(dd,J=4.8,4.0Hz,1H). 13 C NMR (101MHz, CDCl3) δ 179.78, 143.64, 138.19, 136.72, 135.68, 135.47, 132.38, 128.20, 127.80, 125.76, 124.10, 123.66, 122.71. HRMS (EI+): m / z Calculated values: C 13 H7ClOS2 277.9627, measured value: 277.9629.

[0230] Example 7 Synthesis of Compound I-63

[0231]

[0232] Using suitable starting materials, compound I-63 was synthesized using a similar procedure to that used in the synthesis of compound I-3.

[0233] 1H NMR (400MHz, DMSO-d6) δ11.87(s,1H),8.35(s,1H),8.22(dd,J=4.2,0.8Hz,1H),7.75(dd ,J=8.4,0.8Hz,1H),7.76(d,J=8.4Hz,1H),7.45–7.40(m,2H),7.26(s,1H),3.98(s,3H). 13 C NMR (101MHz, DMSO) δ 177.98, 168, 32, 143.45, 138.71, 133.91, 133.46, 133.22, 128.62, 127.19, 124.89, 122.89, 121.29, 111.54, 110.29, 54.59. HRMS (EI+): m / z Calculated values: C 15 H 11 NO3S 285.0460, measured value: 285.0468.

[0234] Example 8 Synthesis of Compound I-64

[0235]

[0236] Using suitable starting materials, compound I-64 was synthesized using a similar procedure to that used in the synthesis of compound I-3.

[0237] 1 H NMR(400MHz,Chloroform-d)δ8.51(s,1H),7.92(d,J=8.0Hz,1H),7.84(d,J=8.4Hz,1H) ,7.69(d,J=7.6Hz,2H),7.61(d,J=8.4Hz,1H),7.49–7.33(m,3H),7.28(t,J=7.4Hz,1H). 13 C NMR (101MHz, CDCl3) δ 175.25, 154.87, 151.47, 141.57, 140.91, 138.30, 130.77, 127.33, 126.65, 125.93, 125.35, 124.06, 123.08, 122.29, 121.77, 113.99, 111.42. HRMS (EI+): m / z Calculated values: C 17 H 10 O2S 278.0402, measured value: 278.0403.

[0238] Example 9 Preparation of benzofuran-2-yl(thiophen-2-yl) methyl ketone, namely compound I-1

[0239]

[0240] 1.464 g (12 mmol) of salicylaldehyde was added to 100 mL of acetonitrile solution containing 2.050 g (10 mmol) of 2-(2-bromoacetyl)thiophene. The mixture was heated to reflux, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed under reduced pressure, and 100 mL of water was added to the residue. The mixture was extracted with dichloromethane (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 1.938 g of a white solid, with a yield of 85%.

[0241] 1 H NMR(400MHz,Chloroform-d)δ8.34(d,J=4.0Hz,1H),7.80–7.70(m,3H),7.65(d,J =8.4Hz,1H),7.51(t,J=8.0Hz,1H),7.35(t,J=8.0Hz,1H),7.27(t,J=4.0Hz,1H). 13 C NMR (101MHz, CDCl3) δ 175.03, 155.80, 152.56, 142.30, 134.60, 134.47, 128.38, 128.15, 127.02, 124.02, 123.24, 114.58, 112.40. HRMS (EI+): m / z Calculated values: C 13 Measured value of H8O2S228.0245: 228.0246.

[0242] Example 10 Synthesis of Compound I-11

[0243]

[0244] Using suitable starting materials, compound I-11 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0245] 1 H NMR (400MHz, DMSO-d6) δ8.43(dd,J=3.8,1.0Hz,1H),8.17(dd,J=5.0,1.0Hz,1H),7.90(d ,J=7.8Hz,1H),7.79(d,J=8.4Hz,1H),7.65–7.56(m,1H),7.47–7.33(m,2H),2.98(s,3H). 13C NMR (101MHz, DMSO) δ 175.36, 153.66, 146.16, 142.64, 135.80, 134.78, 132.58, 128.94, 128.68, 127.52, 123.68, 121.69, 112.31, 16.21. HRMS (EI+): m / z calculated values: C 14 H 10 O2S 242.0402 Measured value: 242.0401.

[0246] Example 11 Synthesis of Compound I-20

[0247]

[0248] Using suitable starting materials, compound I-20 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0249] 1 H NMR (400MHz, Chloroform-d) δ7.69 (dd, J=4.0, 0.8Hz, 1H), 7.69 (dd, J=4.8, 1.0Hz, 1H), 7.66–7. 56(m,2H),7.26(dd,J=8.6,1.4Hz,1H),7.17(dd,J=5.0,3.8Hz,1H),7.04(td,J=9.0,2.2Hz,1H). 19 F NMR (376MHz, CDCl3) δ-110.54. HRMS (EI+): m / z Calculated value: C 13 H7FO2S 246.0151 Measured value: 246.0148.

[0250] Example 12 Synthesis of Compound I-25

[0251]

[0252] Using suitable starting materials, compound I-25 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0253] 1 H NMR (400MHz, DMSO-d6) δ8.37(d,J=3.6Hz,1H),8.22(d,J=5.2Hz,1H),7.92(s,2H),7.85(d,J=8.8Hz,1H),7.60(dd,J=9.0,1.8Hz,1H),7.47–7.34(m,1H). 13C NMR (101MHz, DMSO) δ 173.98, 153.51, 152.49, 141.37, 136.39, 135.05, 129.14, 128.45, 128.36, 128.18, 122.73, 114.26, 114.04. HRMS (EI+): m / z Calculated values: C 13 Measured value of H7ClO2S 261.9855: 261.9858.

[0254] Example 13 Synthesis of Compound I-33

[0255]

[0256] Using suitable starting materials, compound I-33 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0257] 1 H NMR(400MHz,Chloroform-d)δ8.25(d,J=3.8Hz,1H),7.69(d,J=4.8Hz,1H),7.58(s ,1H),7.44(t,J=4.2Hz,2H),7.24(d,J=8.6Hz,1H),7.20–7.15(m,2H)2.40(s,3H). 13 C NMR (101MHz, CDCl3) δ 174.03, 153.31, 151.63, 141.32, 133.46, 133.38, 132.62, 128.74, 127.31, 126.08, 121.66, 113.40, 110.86, 20.31. HRMS (EI+): m / z Calculated values: C 13 Measured value of H7BrO2S242.04O2: 242.0397.

[0258] Example 14 Synthesis of Compound I-37

[0259]

[0260] Using suitable starting materials, compound I-37 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0261] 1H NMR(400MHz,Chloroform-d)δ8.31(d,J=3.6Hz,1H),7.75(d,J=5.2Hz,1H),7.65(s, 1H),7.55–7.48(m,1H),7.24(dd,J=5.0,3.8Hz,1H),7.15–7.08(m,2H),3.86(s,3H). 13 C NMR (101MHz, CDCl3) δ 174.86, 156.70, 153.26, 150.98, 142.30, 134.51, 134.43, 128.34, 127.54, 118.34, 114.57, 113.04, 103.86, 55.87. HRMS (EI+): m / z Calculated values: C 14 H 10 Measured value of O3S258.0351: 258.0350.

[0262] Example 15 Synthesis of Compound I-41

[0263]

[0264] Using suitable starting materials, compound I-41 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0265] 1 H NMR (400MHz, Chloroform-d) δ8.33(dd,J=3.8,1.0Hz,1H),8.07(s,1H),7.81(dd,J=5.0,1.0Hz,1H),7.76(m,3H),7.31–7.23(m,1H). 19 F NMR (376MHz, CDCl3) δ -61.28. HRMS (EI+): m / z Calculated value: C 14 H7F3O2S 296.0119, measured value: 296.0120.

[0266] Example 16 Synthesis of Compound I-43

[0267]

[0268] Using suitable starting materials, compound I-43 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0269] 1H NMR (400MHz, DMSO-d6) δ8.44(s,1H),8.39(d,J=3.6Hz,1H),8.23(d,J=4.8Hz,1H),8.03(dd,J=17.6,8.4Hz,3H),7.40(t,J=4.4Hz,1H). 13 C NMR (101MHz, DMSO) δ 174.02, 156.55, 152.86, 141.24, 136.74, 135.37, 131.44, 129.29, 129.21, 127.35, 118.74, 114.42, 114.11, 107.15. HRMS (EI+): m / z Calculated values: C 14 H7NO2S 253.0197, measured value: 253.0200.

[0270] Example 17 Synthesis of Compound I-44

[0271]

[0272] Using suitable starting materials, compound I-44 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0273] 1 H NMR(400MHz,Chloroform-d)δ8.29(d,J=4.0Hz,1H),7.82–7.75(m,2H),7.72(d ,J=4.0Hz,1H),7.65(d,J=8.4Hz,1H),7.59–7.53(m,1H),7.38(t,J=7.6Hz,1H). 19 FNMR (376MHz, CDCl3) δ -58.24. HRMS (EI+): m / z calculated value: C 14 H7F3O3S312.0068, measured value: 312.0070.

[0274] Example 18 Synthesis of Compound I-46

[0275]

[0276] Using suitable starting materials, compound I-46 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0277] 1H NMR(400MHz,DMSO-d6)δ8.31(d,J=3.6Hz,1H),8.14(d,J=4.8Hz,1H),7.76(s,1H ),7.46(d,J=4.2Hz,1H),7.40–7.31(t,J=8.8Hz,1H),6.89(m,2H),5.16(s,2H). 13 C NMR (101MHz, DMSO) δ 174.03, 151.35, 148.80, 145.69, 141.85, 135.61, 134.43, 129.01, 127.51, 118.07, 114.75, 112.21, 104.11. HRMS (EI+): m / z Calculated values: C 13 H9NO2S 243.0354, measured value: 243.0358.

[0278] Example 19 Preparation of (5-phenylbenzofuran-2-yl)(thiophen-2-yl)methyl ketone, namely compound I-48

[0279]

[0280] To a mixed solvent of dioxane and water containing 0.307 g (1 mmol) of I–29, 57.75 mg (0.05 mmol) of tetraphenylphosphine palladium, and 0.276 g (2 mmol) of potassium carbonate, 0.163 g (1.2 mmol) of p-tolueneboronic acid was added. The mixture was refluxed under argon protection, and the reaction was monitored by TLC. After the reaction was complete, the mixture was filtered through diatomaceous earth. The filtrate was collected, the solvent was removed by vacuum distillation, and 100 mL of water was added to the residue. The residue was extracted with dichloromethane (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 0.261 g of a pale yellow solid, with a yield of 82%.

[0281] 1 H NMR(400MHz,Chloroform-d)δ8.31(dd,J=3.8,1.0Hz,1H),7.99–7.89(m,2H),7.85(d,J=2.0Hz,1H),7.79(dd, J=5.0,1.0Hz,1H),7.64(d,J=0.4Hz,1H),7.63–7.57(m,3H),7.52(d,J=8.8Hz,1H),7.29–7.21(m,1H),2.57(s 3H). 13CNMR (101MHz, CDCl3) δ 174.69, 154.39, 153.49, 141.99, 135.01, 134.66, 133.91, 131.09, 129.20, 128.88, 128.46, 126.21, 125.70, 121.69, 117.12, 113.91, 113.46, 25.76. HRMS (EI+): m / z Calculated value: C 20 H 14 O2S318.0715; found: 318.0717.

[0282] Example 20 Synthesis of Compound I-96

[0283]

[0284] Using suitable starting materials, compound I-96 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0285] 1 H NMR(400MHz,Chloroform-d)δ7.90(m,J=0.4Hz,1H),7.79–7.73(m,2H),7.70(d,J=4.0Hz,1H),7 .64(d,J=8.0Hz,1H),7.50(t,J=8.0Hz,1H),7.34(t,J=8.0Hz,1H),6.67(dd,J=3.6,1.6Hz,1H). 13 C NMR (101MHz, CDCl3) δ 170.07, 155.74, 151.63, 151.51, 147.15, 128.33, 127.14, 123.99, 123.37, 120.37, 115.46, 112.62, 112.43. HRMS (EI+): m / z Calculated values: C 13 H8O3 212.0473, measured value: 212.0475.

[0286] Example 21 Synthesis of Compound I-97

[0287]

[0288] Using suitable starting materials, compound I-97 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0289] 1H NMR(400MHz,Chloroform-d)δ9.76(s,1H),7.73(d,J=7.8Hz,1H),7.68(s,1H),7.63(dd,J=8.4,0.9Hz,1H),7.58(ddd,J=4.0,2 .6,1.3Hz,1H),7.48(ddd,J=8.4,7.4,1.3Hz,1H),7.37–7.28(m,1H),7.18(td,J=2.6,1.8Hz,1H),6.43(dt,J=4.0,2.2Hz,1H). 13 C NMR (101MHz, DMSO) δ 166.5, 150.4, 147.8, 125.3, 122.4, 121.9, 120.4, 118.6, 117.7, 113.8, 108.0, 107.0, 106.4. HRMS (EI+): m / z calculated values: C 13 H9NO2 211.0633, measured value: 211.0635.

[0290] Example 22 Synthesis of Compound I-103

[0291]

[0292] Using suitable starting materials, compound I-103 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0293] 1 H NMR(400MHz,Chloroform-d)δ8.54(d,J=3.2Hz,1H),7.82(d,J=4.8Hz,1H),7.74(d,J=7.6Hz,1H ),7.70–7.60(m,2H),7.50(t,J=7.2Hz,1H),7.41(dd,J=5.0,3.0Hz,1H),7.34(t,J=7.4Hz,1H). 13 C NMR (101MHz, CDCl3) δ 177.01, 155.82, 153.12, 140.21, 134.11, 128.39, 128.15, 127.01, 126.08, 123.99, 123.23, 114.92, 112.43. HRMS (EI+): m / z Calculated values: C 13 Measured value of H8O2S 228.0245: 228.0244.

[0294] Example 23 Synthesis of Compound I-112

[0295]

[0296] Using suitable starting materials, compound I-112 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0297] 1 H NMR(400MHz,Chloroform-d)δ8.16(d,J=7.6Hz,1H),7.75(d,J=7.6Hz,1H),7.71(s,1H),7 .63(d,J=8.4Hz,1H),7.51(t,J=7.8Hz,1H),7.35(t,J=7.6Hz,1H),7.08(d,J=4.4Hz,1H). 13 C NMR (101MHz, CDCl3) δ 173.78, 155.80, 152.25, 140.75, 140.72, 134.32, 128.34, 127.90, 126.89, 124.15, 123.29, 114.68, 112.36. HRMS (EI+): m / z Calculated values: C 13 H7ClO2S 261.9855, measured value: 261.9854.

[0298] Example 24 Synthesis of Compound I-115

[0299]

[0300] Using suitable starting materials, compound I-115 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0301] 1 H NMR(400MHz,Chloroform-d)δ8.09(d,J=3.8Hz,1H),7.66(d,J=7.8Hz,1H),7.60(s,1H),7.56(d ,J=8.4Hz,1H),7.42(t,J=8.4Hz,1H),7.26(t,J=7.6Hz,1H),6.85(d,J=4.8Hz,1H),2.53(s,3H). 13 C NMR (101MHz, CDCl3) δ 174.64, 155.70, 152.76, 150.96, 140.13, 135.30, 127.91, 127.24, 127.05, 123.92, 123.13, 114.07, 112.34, 16.06. HRMS (EI+): m / z Calculated values: C 14 H 10 O2S 242.0402, measured value: 242.0403.

[0302] Example 25 Synthesis of Compound I-120

[0303]

[0304] Using suitable starting materials, compound I-120 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0305] 1 H NMR(400MHz,DMSO-d6)δ8.42(d,J=3.8Hz,1H),8.20(d,J=4.2Hz,1H),8.10(s,1H),7.8 8(d,J=7.8Hz,1H),7.80(d,J=8.2Hz,1H),7.66(t,J=7.4Hz,1H),7.46(t,J=7.2Hz,1H). 13 C NMR (101MHz, DMSO) δ 172.45, 156.33, 150.51, 148.32, 140.54, 134.05, 130.51, 127.23, 126.43, 122.63, 117.24, 115.36, 112.27, 111.56. HRMS (EI+): m / z Calculated values: C 14 H7NO3, 237.0426, measured value: 237.0428.

[0306] Example 26 Synthesis of Compound I-148

[0307]

[0308] Using suitable starting materials, compound I-148 was synthesized using a similar procedure to that used in the synthesis of compound I-1.

[0309] 1 H NMR (400MHz, DMSO-d6) δ8.27 (dd, J=4.0, 1.2Hz, 1H), 8.17 (dd, J=5.0, 1.4Hz, 1H), 7.90 (d, J= 8.0Hz,1H),7.71–7.65(m,4H),7.53–7.38(m,4H),7.31(dd,J=4.8,4.0Hz,1H),4.55(s,2H). 13C NMR (101MHz, DMSO) δ 176.12, 152.65, 144.44, 141.25, 136.47, 134.36, 130.26, 129.72, 128.48, 128.24, 128.25, 128.15, 127.33, 124.50, 121.28, 112.14.30.52. HRMS (EI+): m / z Calculated values: C 20 H 14 O2S 318.0715; found:318.0716.

[0310] Example 27 Preparation of (3-aminobenzofuran-2-yl)(thiophen-2-yl)methyl ketone, namely compound I-150

[0311]

[0312] 0.21 g (1 mmol) of 2-bromo-1-(thiophene-2-yl)ethyl-1-one was added to 5 mL of DMF solution containing 0.12 g (1 mmol) of o-hydroxybenzonitrile and 0.65 g (2 mmol) of cesium carbonate. The mixture was stirred at room temperature, and the reaction was monitored by TLC. After the reaction was complete, ice water was added, and a solid precipitated. The solid was filtered and washed with ice water. The filter cake was separated by column chromatography to give 0.103 g of a pale yellow solid, with a yield of 79.5%.

[0313] 1 H NMR(400MHz,Chloroform-d)δ8.32(d,J=4.0Hz,1H),7.77-7.71(m,2H),7.64(d,J=8.4H z, 1H), 7.50 (t, J = 8.4Hz, 1H), 7.34 (t, J = 8.0Hz, 1H), 7.25 (d, J = 9.0Hz, 1H), 6.02 (s, 2H). 13 C NMR (101MHz, CDCl3) δ 175.03, 155.80, 144.27, 142.30, 134.60, 134.47, 128.38, 128.15, 127.02, 124.02, 123.24, 114.58, 112.40. HRMS (EI+): m / z Calculated values: C 13 H9NO2S243.0354; found:243.0347.

[0314] Example 28 Preparation of N-(2-(thiophene-2-carbonyl)benzofuran-3-yl)acetamide, i.e., compound I-151

[0315]

[0316] 0.06 g (0.5 mmol) of 4-dimethylaminopyridine was added to 50 mL of acetic anhydride solution containing 2.43 g (10 mmol) of compound I-150. The mixture was stirred at room temperature, and the reaction was monitored by TLC. The reaction mixture was filtered, and the filter cake was recrystallized from ethanol to give 0.92 g of a pale yellow solid, with a yield of 32%.

[0317] 1 H NMR (400MHz, DMSO-d6) δ10.44(s,1H),8.41(dd,J=3.8,1.4Hz,1H),8.18(dd,J=5.2,1.2Hz,1H), 8.08(d,J=8.0Hz,1H),7.77(d,J=8.4Hz,1H),7.66–7.59(m,1H),7.41–7.34(m,2H),2.22(s,3H). 13 C NMR (101MHz, DMSO-d6) δ 178.04, 176.43, 158.75, 145.37, 144.32, 133.40, 131.67, 129.48, 128.24, 125.42, 123.91, 123.44, 113.91, 112.98, 23.08. HRMS (EI+): m / z Calculated values: C 15 H 11 NO3S 285.0460; found:285.0465.

[0318] Example 29 Synthesis of Compound I-153

[0319]

[0320] Using suitable starting materials, compound I-153 was synthesized using a similar procedure to that used in the synthesis of compound I-151.

[0321] 1 H NMR (400MHz, Chloroform-d) δ8.11(dd,J=4.0,1.2Hz,1H),7.82–7.72(m,3H),7.33–7.24(m,2H),7.18(dd,J=5.2,4.0Hz,1H). 19 F NMR (376MHz, CDCl3) δ-72.6. HRMS (EI+): m / z Calculated value: C 14 H8F3NO4S2 374.9847; found:374.9848.

[0322] Example 30: Preparation of (3-(methoxymethyl)benzofuran-2-yl)(thiophen-2-yl)methyl ketone, namely compound I-149.

[0323] 30.1 Preparation of (3-(bromomethyl)benzofuran-2-yl)(thiophen-2-yl)methyl ketone

[0324]

[0325] To a 30 mL carbon tetrachloride solution containing 2.43 g (10 mmol) of compound I-11, a 20 mL carbon tetrachloride solution containing 1.87 g (10.5 mmol) of NBS and 0.24 g (1 mmol) of benzoyl peroxide was added dropwise. The mixture was stirred and heated to reflux, and the reaction was monitored by TLC. After the reaction was complete, the mixture was filtered, and the filtrate was collected. The solvent was removed by vacuum evaporation to obtain a pale yellow solid, which was used directly in the next step without further treatment.

[0326] 30.2 Preparation of (3-(methoxymethyl)benzofuran-2-yl)(thiophen-2-yl)methyl ketone, i.e., compound I-149

[0327]

[0328] Add 0.64 g (20 mmol) of sodium methoxide to a 20 mL methanol solution containing 3.21 g (10 mmol) of the obtained intermediate, stir, and heat to reflux. Monitor the reaction progress by TLC. After the reaction is complete, remove the solvent under reduced pressure, add 100 mL of water to the residue, and extract with dichloromethane (100 mL × 3). Dry the organic phase with anhydrous sodium sulfate, concentrate, and separate by column chromatography to give 0.847 g of white solid, yield 31.1%.

[0329] 1 H NMR (400MHz, DMSO-d6) δ8.32(dd,J=3.8,1.0Hz,1H),8.12(dd,J=5.0,1.0Hz,1H),7.84(d,J=7.8 Hz,1H),7.75(d,J=8.4Hz,1H),7.62–7.53(m,1H),7.45–7.31(m,2H),5.08(s,2H),3.36(s,3H). 13 C NMR (101MHz, DMSO) δ 172.32, 154.61, 143.16, 141.24, 135.75, 134.68, 132.38, 129.02, 128.48, 126.59, 123.48, 122.54, 111.21, 62.42, 58.92. HRMS (EI+): m / z Calculated values: C 15 H 12 O3S 272.0507 Measured value: 272.0504.

[0330] Example 31 Preparation of thiophene-2-yl(3-vinylbenzofuran-2-yl) methyl ketone, namely compound I-13

[0331] 31.1 Preparation of 2-(2-iodophenoxy)-1-(thiophen-2-yl)ethyl-1-one

[0332]

[0333] To a 20 mL DMF solution containing 2.54 g (10 mmol) of 5-chloro-2-iodophenol and 2.76 g (20 mmol) of potassium carbonate, a 5 mL DMF solution containing 2.05 g (10 mmol) of 2-bromo-1-(thiophene-2-yl)ethyl-1-one was added dropwise. The mixture was stirred at room temperature, and the reaction was monitored by TLC. After the reaction was complete, 200 mL of water was added to the reaction solution, and the mixture was extracted with ethyl acetate (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give intermediate I 3.21 g, with a yield of 84.90%.

[0334] 31.2 Preparation of 2-(2-(3-hydroxyprop-1-yn-1-yl)phenoxy)-1-(thiophen-2-yl)acet-1-one

[0335]

[0336] To 40 mL (1:1) of a mixed solution of DMF and triethylamine containing 1.89 g (5 mmol) of the intermediate and 0.34 g (6 mmol) of propynyl alcohol, 0.18 g (0.25 mmol) of palladium dichloride bis(triphenylphosphine) was added and the mixture was stirred at room temperature for 10 minutes. Then, 0.10 g (0.5 mmol) of cuprous iodide was added, and the mixture was stirred at room temperature under argon protection. The reaction was monitored by TLC. After the reaction was complete, the reaction solution was filtered through diatomaceous earth, the solvent was removed under reduced pressure, the solution was concentrated, and column chromatography was performed to obtain 1.03 g of intermediate II, with a yield of 67.23%.

[0337] 31.3 Preparation of ethyl carbonate (3-(2-(2-oxo-2-(thiophen-2-yl)ethoxy)phenyl)prop-2-yl-1-ethyl)carbonate

[0338]

[0339] Under ice bath conditions, 5 mL of dichloromethane solution containing 1.74 g (16 mmol) of ethyl chloroformate was added dropwise to 20 mL of dichloromethane solution containing 1.23 g (4 mmol), 1.62 g (16 mmol) of triethylamine, and 0.12 g (1 mmol) of DMAP. The mixture was stirred at room temperature, and the reaction was monitored by TLC. After the reaction was complete, 50 mL of water was added to the reaction solution, and the mixture was extracted with dichloromethane (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 1.28 g of intermediate III, with a yield of 84.72%.

[0340] 31.4 Preparation of thiophene-2-yl(3-vinylbenzofuran-2-yl) methyl ketone, i.e., compound I-13

[0341]

[0342] A 5 mL solution of DMF containing 0.38 g (1 mmol) of intermediate III and 0.27 g (2 mmol) of potassium carbonate was stirred at room temperature for 5 minutes. Then, 16.8 mg (0.02 mmol) of palladium on carbon was added, and the mixture was heated to 60 °C. The reaction was monitored by TLC. After the reaction was complete, 50 mL of water was added to the reaction solution, and the mixture was extracted with ethyl acetate (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 0.22 g of a pale yellow solid, with a yield of 78.65%.

[0343] 1 H NMR (400MHz, DMSO-d6) δ8.43(dd,J=3.8,1.0Hz,1H),8.17(dd,J=5.0,1.0Hz,1H),7.90(d,J=7.8Hz,1H),7.79( d,J=8.4Hz,1H),7.65–7.56(m,1H),7.47–7.33(m,2H),6.10(d,J=2.0Hz,1H),5.66(dd,J=2.4Hz,18.8Hz,1H). 13 C NMR (101MHz, DMSO) δ176.26,152.55,147.35,143.24,138.23,136.78,133.28,131.68,128.68,128.45,127.81,127.06,123.87,120.65,111.21.

[0344] Example 32 Preparation of (E)-benzofuran-2-yl(thiophen-2-yl)methyl ketone O-ethyl oxime, namely compound I-134.

[0345]

[0346] 1.042 g (15 mmol) of hydroxylamine hydrochloride was added to an 80% ethanol solution containing 0.799 g (20 mmol) of sodium hydroxide. The mixture was stirred at room temperature for half an hour, followed by the addition of 2.280 g (10 mmol) of benzofuran-2-yl(thiophen-2-yl) methyl ketone, compound I-2. The mixture was heated to reflux, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed under reduced pressure, and 100 mL of water was added to the residue. The mixture was extracted with dichloromethane (100 mL × 3), dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 1.628 g of a white solid, with a yield of 67%.

[0347] 1 H NMR (400MHz, DMSO-d6) δ12.53(s,1H),7.85(d,J=0.8Hz,1H),7.80(d,J=7.2Hz,1H),7.72–7.68(m,1H),7.66(dd,J=3.6,1 .2Hz,1H),7.61(dd,J=5.2,1.2Hz,1H),7.45(ddd,J=8.4,7.4,1.2Hz,1H),7.38–7.31(m,1H),7.18(dd,J=5.0,3.8Hz,1H). 13 C NMR (101MHz, DMSO) δ 152.87, 144.77, 141.20, 137.05, 128.48, 127.59, 127.49, 127.11, 126.28, 123.48, 122.25, 113.18, 111.52. HRMS (EI+): m / z Calculated values: C 13 H9NO2S 243.0354, measured value: 243.0352.

[0348] Example 33 Preparation of benzofuran-2-yl(thiophen-2-yl)methyl ketone O-(3,4,4-trifluorobut-3-en-1-yl)oxime, namely compound I-138

[0349]

[0350] 2.430 g (10 mmol) of I-134 was added to 100 mL of acetonitrile solution containing 2.268 g (12 mmol) of 4-bromo-1,1,2-trifluoro-1-butene and 2.073 g (15 mmol) of potassium carbonate. The mixture was heated to reflux, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed under reduced pressure, and 100 mL of water was added to the residue. The mixture was extracted with dichloromethane (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 2.114 g of a yellow oily liquid, with a yield of 78%.

[0351] 1H NMR(400MHz,Chloroform-d)δ7.56–7.52(m,3H),7.49(d,J=8.4Hz,1H),7.28(t,J=4.0Hz,1H),7.19(t,J=8.2Hz 1H),7.07–7.03(m,1H),6.98(s,1H),4.48(t,J=6.2Hz,2H),2.82–2.66(m,2H). 19 F NMR (376MHz, Chloroform-d) δ -103.32, -123.53, -175.31. HRMS (EI+): m / z calculated values: C 17 H 12 F3NO2S, 351.0541, measured value: 351.0543.

[0352] Example 34 Preparation of (1-allyl-1H-indol-2-yl)(thiophen-2-yl)methyl ketone, i.e., compound I-17

[0353]

[0354] Compound I-3 227 mg (1 mmol), iodobenzene 306 mg (1.5 mmol), potassium hydroxide 84 mg (1.5 mmol), and cuprous oxide 1.43 mg (0.001 mmol) were added to a solution containing 10 mL of N,N-dimethylformamide. The mixture was heated to reflux under argon protection, and the reaction was monitored by TLC. After the reaction was complete, 100 mL of water was added to the residue, and the mixture was extracted with dichloromethane (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 45 mg of a pale yellow solid, with a yield of 15%.

[0355] 1 H NMR(400MHz, DMSO-d6)δ8.12(dd,J=4.0,1.2Hz,1H),8.1(dd,J=4.2,1.4Hz,1H), 7.75-7.63(m,5H),7.54-7.43(m,4H),7.36-7.29(m,1H),7.11(t,J=6.8Hz,1H). 13 CNMR (101MHz, DMSO) δ 180.38, 141.43, 136.61, 134.22, 133.76, 133.48, 132.95, 128.72, 127.09, 126.23, 125.59, 125.33, 123.21, 122.79, 120.39, 112.66, 110.09. HRMS (EI+): m / z Calculated value: C 19 H 13NOS 303.0718 Measured value: 303.0720.

[0356] Example 35 Preparation of benzo[d]thiazol-2-yl(thiophen-2-yl) methyl ketone, i.e., compound I-5

[0357] 35.1 Preparation of benzo[d]thiazole-2-carbonyl chloride

[0358]

[0359] 1.792 g (10 mmol) of benzothiazole-2-carboxylic acid was added to 20 mL of thionyl chloride and heated to reflux. The reaction progress was monitored by GC. After the reaction was completed, the solvent was removed by vacuum distillation and the mixture was directly added to the next step.

[0360] 35.2 Preparation of benzo[d]thiazol-2-yl(thiophen-2-yl) methyl ketone, i.e., compound I-5

[0361]

[0362] 10 mL of anhydrous dichloromethane solution containing the intermediate from the previous step was added to 50 mL of anhydrous dichloromethane solution containing 1.600 g (12 mmol) of anhydrous aluminum trichloride. The mixture was stirred at room temperature for half an hour, followed by dropwise addition of 1.009 g (12 mmol) of thiophene in 50 mL of anhydrous dichloromethane solution. The reaction was monitored by TLC. After the reaction was complete, 100 mL of water was added to the residue, and the mixture was extracted with dichloromethane (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 1.104 g of a pale yellow solid, with a yield of 45%.

[0363] 1 H NMR (400MHz, Chloroform-d) δ8.77(d,J=4.4Hz,1H),8.25(d,J=7.2Hz,1H),8.02(d,J=7.6Hz,1H),7.85(d,J=4.8Hz,1H),7.58(m,2H),7.30–7.26(m,1H). 13 C NMR (101MHz, CDCl3) δ 177.01, 166.63, 153.74, 139.74, 137.40, 137.04, 136.79, 128.47, 127.57, 126.96, 125.59, 122.27. HRMS (EI+): m / z Calculated values: C 12 H7NOS2, 244.9969, measured value: 244.9967.

[0364] Example 36 Synthesis of Compound I-83

[0365]

[0366] Using suitable starting materials, compound I-83 was synthesized using a similar procedure to that used in the synthesis of compound I-5.

[0367] 1 H NMR (400MHz, Chloroform-d) δ8.84(d,J=3.6Hz,1H),7.89(dd,J=15.4,6.4Hz,2H),7.62(d,J=7.6Hz,1H),7.48(t,J=8.0Hz,1H),7.29(t,J=4.4Hz,1H). 13 C NMR (101MHz, CDCl3) δ 176.51, 167.12, 150.83, 139.47, 138.44, 137.82, 137.30, 130.54, 128.69, 128.10, 127.12, 120.80. HRMS (EI+): m / z Calculated values: C 12 H6ClNOS2, 278.9579, measured value: 278.9576.

[0368] Example 37 Synthesis of Compound I-113

[0369]

[0370] Using suitable starting materials, compound I-113 was synthesized using a similar procedure to that used in the synthesis of compound I-5.

[0371] 1 H NMR (400MHz, Chloroform-d) δ7.72(d,J=8.0Hz,2H),7.63(d,J=8.8Hz,1H),7.58–7.54(m,2H),7.43–7.37(m,1H). 13 C NMR (101MHz, CDCl3) δ 178.25, 168.31, 154.14, 134.05, 128.94, 128.25, 127.08, 127.01, 123.87, 122.26, 114.12, 111.27. HRMS (EI+): m / z Calculated values: C 12 H6ClNOS2 278.9579, measured value: 278.9582.

[0372] Example 38 Preparation of benzo[d]oxazol-2-yl(thiophen-2-yl)methyl ketone, i.e., I-4

[0373] 38.1 Preparation of 2-bromo-1-(thien-2-yl)ethyl-1-one and 2,2-dibromo-1-(thien-2-yl)ethyl-1-one

[0374]

[0375] 1.262 g (10 mmol) of 2-acetylthiophene and 3.350 g (15 mmol) of ketone bromide were added to 100 mL of acetonitrile and heated to reflux. The reaction was monitored by TLC. After the reaction was complete, the solvent was removed under reduced pressure, and 50 mL of water was added to the residue. The residue was extracted with dichloromethane (80 mL × 2). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give two brown liquids: 0.693 g (34% yield) and 1.127 g (40% yield).

[0376] 1 H NMR (400MHz, Chloroform-d) δ8.02(dd,J=4.0,0.8Hz,1H),7.80(dd,J=4.8,0.8Hz,1H),7.22(t,J=4.4Hz,1H),6.51(s,1H).

[0377] 38.2 Preparation of benzo[d]oxazol-2-yl(thiophen-2-yl)methyl ketone, i.e., compound I-4

[0378]

[0379] 0.218 g (2 mmol) of o-aminophenol was added to 40 mL of N,N-dimethylformamide solution containing 0.585 g (8 mmol) of diethylamine. Then, 10 mL of N,N-dimethylformamide solution containing 0.676 g (2.4 mmol) of 2,2-dibromo-1-(thiophene-2-yl)ethyl-1-one was added dropwise at room temperature. The mixture was heated to 90 °C, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed under reduced pressure. 50 mL of water was added to the residue, and the mixture was extracted with dichloromethane (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 0.220 g of a yellow solid, with a yield of 48%.

[0380] 1 H NMR(400MHz,Chloroform-d)δ8.69(d,J=3.6Hz,1H),7.89(d,J=8.0Hz,1H),7.80(d,J=4.6Hz,1 H),7.65(d,J=8.2Hz,1H),7.49(t,J=7.4Hz,1H),7.42(t,J=7.6Hz,1H),7.21(t,J=4.4Hz,1H). 13C NMR (101MHz, CDCl3) δ 171.17, 155.85, 149.59, 139.71, 139.58, 136.56, 135.95, 127.69, 127.36, 124.74, 121.29, 110.90. HRMS (EI+): m / z Calculated values: C 12 H8N2OS, 229.0198, measured value: 229.0197.

[0381] Example 39 Preparation of (6-methyl-1H-benzo[d]imidazol-2-yl)(thiophen-2-yl)methyl ketone, i.e., I-78

[0382]

[0383] 0.660 g (5 mmol) of 6-methyl-1H-benzo[d]imidazole and 2.0 mL of triethylamine were added dropwise to 5 mL of pyridine at 0 °C and stirred at low temperature for half an hour. Then, 1.460 g (10 mmol) of 2-thiophene chloride was slowly added dropwise, and the reaction was carried out at room temperature. The reaction progress was monitored by TLC. After the reaction was completed, 5 mL of 6 mmol / L sodium hydroxide solution was added, and the solution was then heated to 100 °C with stirring. After one hour, the reaction solution was cooled to room temperature, and then the pH of the reaction solution was neutralized to 6-7 with 1 mmol / L hydrochloric acid solution. The reaction solution was extracted with dichloromethane (100 mL × 3), the organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 0.508 g of a light yellow solid, with a yield of 42%.

[0384] 1 H NMR(400MHz,DMSO-d6)δ10.72(s,0.5H),10.61(s,0.5H),8.93–8.91(m,1H),7.84–7.82(m,1H),7.74(s,1H), 7.49(d,J=8.3Hz,0.5H),7.38(s,0.5H),7.28–7.26(m,1H),7.20(d,J=8.3Hz,1H),2.52(s,2H),2.51(s,1H); 13 C NMR (101MHz, DMSO) δ 177.21, 147.32, 144.21, 141.21, 137.71, 136.85, 136.35, 133.61, 128.55, 125.73, 121.52, 111.61, 21.87. HRMS (EI+): m / z Calculated values: C 13 H 10 N2OS, 242.0514, measured value: 242.0512.

[0385] Example 40 Preparation of 2-(thiophene-2-ylmethyl)benzo[b]thiophene, i.e., compound I-2

[0386] 40.1 Preparation of 3-(2-iodophenyl)-1-(thiophen-2-yl)prop-1-one

[0387]

[0388] To 10 mL of anhydrous tetrahydrofuran containing 1.479 g (5 mmol) of 2-iodobenzylmethyl bromide, 10 mL of anhydrous tetrahydrofuran solution containing 1.189 g (6 mmol) of ethyl 2-thiophenecarboxylate was added dropwise. Then, 10 mL of anhydrous tetrahydrofuran solution containing 0.180 g (0.65 mmol) of sodium hydroxide was added dropwise. The mixture was stirred at room temperature, and the reaction was monitored by TLC. After the reaction was complete, saturated ammonium chloride solution was added to quench the reaction. The mixture was extracted with ethyl acetate (100 mL × 3 times), and the organic phase was dried over anhydrous sodium sulfate and concentrated. The concentrated substance was added to 8 mL (2 mol / L) sodium hydroxide solution and 8 mL of ethanol, and the mixture was heated to reflux. The reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, and then 10 mL of hydrochloric acid solution (10%) was added. The mixture was then extracted with ethyl acetate (100 mL × 3 times), and the organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to obtain the product.

[0389] 40.2 Preparation of benzo[b]thiophene-2-yl(thiophene-2-yl) methyl ketone, i.e., compound I-2

[0390]

[0391] 0.684 g (2 mmol) of 3-(2-iodophenyl)-1-(thiophen-2-yl)prop-1-one, 0.662 g (6 mmol) of potassium sulfide, and 0.038 g (0.2 mmol) of cuprous iodide were added to 5 mL of N,N-dimethylformamide. The mixture was heated to 130 °C, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, filtered, and the filtrate was extracted with ethyl acetate (50 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 0.415 g of a pale yellow solid, with a yield of 85%.

[0392] 1 H NMR (400MHz, Chloroform-d) δ8.13 (s, 1H), 7.98 (d, J = 3.8Hz, 1H), 7.91 (t, J = 7. 2Hz,2H),7.74(d,J=5.0Hz,1H),7.51–7.40(m,2H),7.22(dd,J=4.8,4.0Hz,1H). 13C NMR (101MHz, CDCl3) δ 180.11, 142.66, 142.48, 142.28, 138.97, 133.89, 133.57, 130.28, 128.09, 127.34, 125.96, 125.10, 122.82. HRMS (EI+): m / z Calculated values: C 13 H8OS2 244.0017, measured value: 244.0018.

[0393] Example 41 Synthesis of Compound I-95

[0394]

[0395] Using suitable starting materials, compound I-95 was synthesized using a similar procedure to that used in the synthesis of compound I-2.

[0396] 1 H NMR (400MHz, Chloroform-d) δ9.17(d,J=1.8Hz,1H),8.89(dd,J=4.8,1.4Hz,1H),8.21-8.16(m,1H),8.04-7.84(m,3H),7.56-7.44(m,3H). 13 C NMR (101MHz, CDCl3) δ 183.32, 157.22, 154.45, 150.15, 149.21, 136.45, 133.72, 129.02, 127.21, 124.07, 123.64, 123.29, 116.44, 113.41. HRMS (EI+): m / z Calculated values: C 14 H9NOS 239.0405, measured value: 239.0407.

[0397] Example 42 Synthesis of Compound I-51

[0398]

[0399] Compound I-51 was prepared using suitable starting materials and a procedure similar to that described for compound I-2.

[0400] 1 H NMR (400MHz, Chloroform-d) δ8.15(s,1H),8.02(d,J=4.2Hz,1H),7.95(t,J=7.8Hz,2H),7.78(s,1H),7.43(d,J=7.8Hz,1H),7.22(dd,J=4.8,4.0Hz,1H). 13C NMR (101MHz, CDCl3) δ180.11,142.66,142.48,142.28,138.97,133.89,133.57,130.28,128.09,127.34,125.96,125.10,122.82. 13 C NMR (101MHz, CDCl3) δ 181.21, 143.57, 142.95, 142.78, 139.51, 134.32, 134.05, 131.45, 127.83, 125.27, 125.45, 123.41, 121.98. HRMS (EI+): m / z Calculated values: C 13 H7ClOS2 277.9627, measured value: 277.9628.

[0401] Example 43 Preparation of 2-(thiophene-2-ylmethyl)benzofuran, i.e., I-128

[0402]

[0403] Under ice bath conditions, a solution of diethyl ether containing 0.227 g (6 mmol) sodium borohydride was added dropwise to 50 mL of anhydrous acetonitrile solution containing 2.280 g (10 mmol) benzofuran-2-yl(thiophen-2-yl) methyl ketone and 5.430 g (50 mmol) trimethylchlorosilane. Then, 3.142 g (50 mmol) of sodium cyanoborohydride was added dropwise. The reaction mixture was brought to room temperature, and the reaction was monitored by TLC. After the reaction was complete, 50 mL of 2 mmol / L hydrochloric acid aqueous solution was added. The mixture was then extracted with ethyl acetate (100 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 1.669 g of a pale yellow solid, with a yield of 78%.

[0404] 1 H NMR (400MHz, Chloroform-d) δ7.48(d,J=7.2Hz,1H),7.42(d,J=8.0Hz,1H),7.25-7.14(m,3H),6.95(t,J=3.6Hz,1H),6.46(s,1H),4.30(s,2H). 13 C NMR (101MHz, CDCl3) δ 156.62, 154.91, 139.22, 128.64, 126.91, 126.02, 124.38, 123.58, 122.56, 111.08, 103.32, 29.21. HRMS (EI+): m / z Calculated values: C 13 H 10OS 214.0452, measured value: 214.0455.

[0405] Example 44 Synthesis of Compound I-132

[0406]

[0407] Compound I-132 was prepared using suitable starting materials and a procedure similar to that described for compound I-128.

[0408] 1 H NMR(400MHz,Chloroform-d)δ8.03(d,J=8.0Hz,1H),7.80(d,J=7.8Hz,1H),7.50(dd,J=8.2,7.4Hz,1H),7.31( dd,J=7.8,7.4Hz,1H),7.25(d,J=5.0Hz,1H),7.06(d,J=3.6Hz,1H),6.99(dd,J=5.0,3.6Hz,1H),4.65(s,2H). 13 C NMR (101MHz, CDCl3) δ 170.28, 153.11, 138.73, 135.62, 127.13, 126.91, 126.01, 125.34, 124.87, 122.76, 121.61, 34.65. HRMS (EI+): m / z Calculated values: C 12 H9NS2 231.0176, measured value: 231.0175.

[0409] Example 45 Preparation of 2-(thiophene-2-ylsulfonyl)benzofuran, namely compound I-142

[0410] 45.1 Preparation of 2-(thiophene-2-ylthio)benzofuran (i.e., compound I-141)

[0411]

[0412] 0.985 g (5 mmol) of 2-bromobenzofuran, 0.697 g (6 mmol) of 2-thiophene thiol, and 0.561 g (10 mmol) of potassium hydroxide were added to 10 mL of dimethyl sulfoxide, and the mixture was heated to 110 °C. The reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature and extracted with ethyl acetate (50 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 0.951 g of a yellow liquid, with a yield of 82%.

[0413] 1H NMR (400MHz, DMSO-d6) δ8.25(dd,J=4.8,1.2Hz,1H),8.01(dd,J=4.0,1.2Hz,1H),7.97(s,1H),7.85( d,J=8.0Hz,1H),7.72(d,J=8.4Hz,1H),7.53(t,J=7.8Hz,1H),7.41–7.32(m,1H),7.33–7.31(m,1H). 13 C NMR (101MHz, DMSO) δ 152.57, 145.11, 138.42, 136.99, 132.44, 129.23, 128.56, 125.22, 125.12, 122.55, 112.11, 111.11. HRMS (EI+): m / z calculated values: C 12 H8O1S2 232.0017, measured value: 232.0019.

[0414] 45.2 Preparation of 2-(thien-2-ylsulfonyl)benzofuran, i.e., compound I-142

[0415]

[0416] At 0 °C, 10 mL of dichloromethane containing 0.345 g (2 mmol) m-chloroperoxybenzoic acid was added dropwise to 10 mL of dichloromethane containing 0.232 g (1 mmol) I-144. The reaction was gradually brought to room temperature, and the reaction progress was monitored by TLC. After the reaction was complete, 10 mL of 10% sodium thiosulfate solution was added to the reaction solution, and the mixture was extracted with dichloromethane (50 mL × 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 0.214 g of a white solid, with a yield of 81%.

[0417] 1 H NMR (400MHz, DMSO-d6) δ8.23(dd,J=4.8,1.2Hz,1H),7.98(dd,J=4.0,1.2Hz,1H),7.93(s,1H),7.84( d,J=8.0Hz,1H),7.74(d,J=8.4Hz,1H),7.57(t,J=7.8Hz,1H),7.46–7.39(m,1H),7.34–7.30(m,1H). 13 C NMR (101MHz, DMSO) δ 155.56, 151.01, 138.97, 137.56, 135.74, 129.03, 128.69, 125.62, 124.71, 123.75, 113.51, 112.32. HRMS (EI+): m / z Calculated values: C 12H8O3S2 263.9915, measured value: 263.9918.

[0418] Example 46 Preparation of 1-methyl-2-(thiophen-2-ylsulfonyl)-1H-indole, namely compound I-143

[0419]

[0420] Compound I-143 was prepared using suitable starting materials and a procedure similar to that described for compound I-142.

[0421] 1 H NMR(400MHz,Chloroform-d)δ7.73(d,J=4.0Hz,1H),7.69(d,J=8.0Hz,1H),7.66(d,J=8.0Hz,1H),7 .37(t,J=9.0Hz,2H),7.33(d,J=8.0Hz),7.19(t,J=8.0Hz,1H),7.09(d,J=7.0Hz,1H),3.95(s,3H); 13 C NMR (101MHz, CDCl3) δ 143.21, 139.62, 135.53, 134.01, 133.44, 127.92, 125.93, 125.24, 123.01, 121.33, 110.53, 110.32, 31.01. HRMS (EI+): m / z Calculated values: C 13 H 11 NO2S2 277.0231, measured value: 277.0233.

[0422] Example 47 Preparation of N-(5-methylthiophene-2-yl)benzofuran-2-carboxamide, namely compound I-144

[0423] 47.1 Preparation of benzofuran-2-carbonyl chloride

[0424]

[0425] Add 1.621 g (10 mmol) of benzofuran-2-carboxylic acid to 20 mL of thionyl chloride, heat to reflux, monitor the reaction progress by GC, and after the reaction is completed, remove the solvent by vacuum distillation and proceed directly to the next step.

[0426] 47.2 Preparation of N-(5-methylthiophen-2-yl)benzofuran-2-carboxamide, i.e., compound I-144

[0427]

[0428] To an 80 mL acetonitrile solution containing 0.565 g (5 mmol) 5-methylthiophene-2-amine and 2.024 g (20 mmol) triethylamine, 10 mL of a solution of the intermediate from the first step reaction was added dropwise at 0 °C. After the addition was complete, the reaction was allowed to proceed at room temperature, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed by vacuum distillation, and 50 mL of water was added to the residue. The residue was extracted with dichloromethane (80 mL × 2). The organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to give 0.925 g of a white solid, with a yield of 72%.

[0429] 1 H NMR (400MHz, DMSO-d6) δ11.94(s,1H),7.84(d,J=8.0Hz,1H),7.77(m,1H),7.73(d,J=8.4Hz,1H),7 .55–7.49(m,1H),7.39(t,J=7.6Hz,1H),7.04(d,J=3.8,1H),6.94(dd,J=3.8Hz,1H),2.38(s,3H). 13 C NMR (101MHz, DMSO) δ 162.72, 157.22, 150.02, 140.21, 126.92, 124.75, 124.32, 121.33, 120.91, 117.02, 111.51, 111.22, 13.28. HRMS (EI+): m / z Calculated values: C 14 H 11 NO2S, 257.0510, measured value: 257.0511.

[0430] Example 48 Synthesis of Compound I-146

[0431]

[0432] Compound I-146 was prepared using suitable starting materials and a procedure similar to that described for compound I-144.

[0433] 1 H NMR(400MHz,Chloroform-d)δ12.81(s,1H),9.78(s,1H),9.31(s,1H),8.01(d, J=1.8Hz,1H),7.41(s,1H),7.20(d,J=3.4Hz,1H),6.78(dd,J=3.3,1.6Hz,1H). 13C NMR (101MHz, CDCl3) δ 163.61, 154.72, 144.27, 143.87, 133.77, 128.31, 126.41, 125.54, 121.45, 117.43. HRMS (EI+): m / z Calculated values: C 10 H7N3OS2, 249.0031, measured value: 249.0033.

[0434] Example 49 Preparation of 4-methyl-N-(thiophen-2-yl)benzofuran-2-sulfonamide, namely compound I-154

[0435]

[0436] 0.26 g (2 mmol) of 2-nitrothiophene, 0.42 g (2.4 mmol) of (4-methylbenzofuran-2-yl)boric acid, 0.33 g (1.2 mmol) of tetrabutylammonium chloride, 0.34 g (2.4 mmol) of potassium carbonate, and 0.89 g (4 mmol) of potassium metabisulfite were added to a pressurized reaction flask containing 10 mL of acetonitrile. The reaction was carried out at 130 °C, and the reaction progress was monitored by TLC. After the reaction was completed, the mixture was filtered through diatomaceous earth, concentrated, and separated by column chromatography to give 0.32 g of a white solid, with a yield of 55.21%.

[0437] 1 H NMR (400MHz, DMSO-d6) δ10.92(s,1H)8.25(dd,J=5.0,1.0Hz,1H),7.97(dd,J=3.8,1.0Hz,1H),7.94(s,1H) ,7.82(d,J=8.0Hz,1H),7.78(d,J=8.2Hz,1H),7.56(t,J=7.6Hz,1H),7.45–7.37(m,1H),7.33–7.29(m,1H). 13 CNMR (101MHz, DMSO) δ 155.62, 152.11, 139.02, 137.45, 136.04, 128.93, 128.79, 126.22, 124.51, 123.65, 112.11, 111.42, 12.31. HRMS (EI+): m / z Calculated value: C 13 H 11 NO3S2 293.0180, measured value: 293.0184.

[0438] Example 50 Preparation of N-phenylbenzofuran-2-carbon thioamide, namely compound I-108

[0439]

[0440] The mixture was stirred at -78°C, and a 1.6M solution of 0.13 g (2 mmol) of n-butyllithium in n-hexane was added to 10 mL of anhydrous tetrahydrofuran containing 0.24 g (2 mmol). After reacting at this temperature for one hour, 5 mL of anhydrous tetrahydrofuran solution containing 0.27 g (2 mmol) of phenyl thioisocyanate was added, and the reaction was gradually brought to room temperature. The reaction was monitored by TLC. After the reaction was complete, 50 mL of n-pentane was added, and a solid precipitated. The reaction mixture was filtered, concentrated, and separated by column chromatography to give 0.45 g of solid, with a yield of 89.21%.

[0441] 1 H NMR (400MHz, DMSO-d6) δ9.75 (s, 1H), 8.21 (d, J = 4.0Hz, 1H), 7.84 (d, J = 8.2Hz), 7.74 (s, 1H), 7. 61(d,J=8.0Hz,1H),7.44(d,J=8.4Hz,1H),,7.28(d,J=8.4Hz,1H),7.01(dd,J=8.8,4.0Hz,1H). 13 C NMR (101MHz, DMSO) δ 182.42, 154.84, 153.52, 139.04, 129.44, 128.72, 127.98, 126.15, 124.07, 123.45, 114.12, 111.23, 107.21. HRMS (EI+): m / z calculated values: C 13 H9NO2S 243.0354, measured value: 243.0358.

[0442] Example 51: Nematicidal activity test of the compound of the present invention

[0443] Root-knot nematodes belong to the phylum Nematoda, order Tylenchida, suborder Tylenchida, superfamily Heteroderidea, subfamily Meloidogyninae, and genus Root-knot nematodes. They are a serious plant parasitic nematode.

[0444] The southern root-knot nematode (Meloidogyne incognita) was used as the test subject, and cucumber seedlings were used as the test host. The test was conducted using a test tube cultivation method.

[0445] Procedure: Prepare a solution of the test sample using acetone and deionized water to the required concentration, and prepare a sufficient number of second-instar root-knot nematode larvae. Plant one-week-old cucumber seedlings in test tubes, add an appropriate amount of the prepared solution, and inoculate approximately 2000 larvae into each test tube. Incubate the test tubes at 20–25°C under 10 hours of light. After 45 days, investigate the results and count the number of root knots on each plant's root system. Each sample is tested three times, with four replicates per sample per test.

[0446] Distilled water was used as a blank control, distilled water with root-knot nematodes was used as a negative control, and tioxazafen and abamectin solutions were used as positive controls.

[0447] Table 1 shows the in vivo nematode inhibition rate of compounds of formula (I).

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460] Example 52: In vitro nematicidal activity test of the compounds of the present invention

[0461] The second instar larvae of the southern root-knot nematode (Meloidogyne incognita) and the pine wood nematode (Bursaphelenchus xylophilus) were used as test subjects, and the well plate method was employed for testing.

[0462] Procedure: Prepare the test sample into a solution of the required concentration and prepare a sufficient quantity of second-instar root-knot nematode larvae or pine wood nematodes. Take a 96-well plate, place 50 μL of the test solution in each well, add an equal volume of nematode suspension to ensure 80–100 second-instar nematodes per well, and cover the plate to prevent moisture evaporation. Place the 96-well plate in a 25°C incubator, protected from light. Each treatment is repeated four times. Distilled water serves as a blank control, distilled water with root-knot nematodes as a negative control, and abamectin solution as a positive control. After 72 hours of treatment, check the number of surviving and dead second-instar nematode larvae, and calculate the mortality rate and corrected mortality rate.

[0463] Table 2 shows the in vitro nematicidal activity of compounds of formula (I).

[0464]

[0465]

[0466]

[0467]

[0468] All documents mentioned in this application are incorporated herein by reference, just as if each document were incorporated herein by reference individually. It should also be understood that after reading the above teachings of the present invention, those skilled in the art may make various changes or modifications to the present invention, and that such equivalents also fall within the scope of the claims appended hereto.

Claims

1. The use of the following compounds or their pesticide-acceptable salts in the preparation of nematicides. The numbers of the compounds are: I-1, I-2, I-3, I-5, I-20, I-21, I-24, I-25, I-28, I-29, I-32, I-33, I-44, I-96, I-97, I-103, I-111, I-112, I-114, I-115, I-128 2. The use as described in claim 1, characterized in that, The numbers of the compounds are: I-1, I-2, I-3, I-5, I-20, I-21, I-24, I-25, I-28, I-29, I-32, I-33, I-44; 3. A nematicide or nematicidal pesticide composition comprising the compound of claim 1 or 2 or a pesticide-acceptable salt thereof and optionally a pesticide-acceptable excipient.

4. The following compounds or their pesticide-acceptable salts, characterized in that, The compounds are numbered: I-20, I-24, I-28, I-32, I-44; 5. A method for killing nematodes, characterized in that, An effective amount of the nematicide or nematicide pesticide composition of claim 3 or the compound of claim 4 or a pesticide-acceptable salt thereof is given to the plant in which nematodes need to be killed.

6. The method as described in claim 5, characterized in that, The nematodes are selected from: root-knot nematodes; cyst nematodes; heterodermal nematodes; grain nematodes; stem and leaf bud nematodes; stinging nematodes; pine nematodes; ring nematodes; bulb nematodes; trypanosome nematodes; spiral nematodes; sheath nematodes; crown nematodes; pseudoroot-nodule nematodes; needle nematodes; nail nematodes; root-rot nematodes; perforating nematodes; kidney-shaped nematodes; residual root nematodes; dwarfing nematodes; citrus nematodes; and xiphoid nematodes.

7. The method as described in claim 6, characterized in that, The root-knot nematodes are *Meloidogynearenaria*, *Meloidogyne chitwoodi*, *Meloidogyneexigua*, *Meloidogyne hapla*, *Meloidogyne incognita*, or *Meloidogyne javanica*; the cyst nematodes are *Globoderarostochiensis*, *Globodera pallida*, or *Globoderatabacum*; the heterodermal nematodes are *Heterodera avenae*, *Heterodera glycines*, *Heterodera schachtii*, or *Heterodera trifolii*; and the grain nematodes are *Anguina*. The nematodes are *Aphelenchoides besseyi* (wheat grain nematode) or *Anguina tritici* (wheat grain nematode); the stem and leaf bud nematodes are *Aphelenchoides besseyi* (rice stem tip nematode), *Aphelenchoides fragariae* (strawberry nematode), or *Aphelenchoides ritzemabosi* (chrysanthemum nematode); the stinging nematode is *Belonolaimus longicaudatus* (weed stinging nematode); the pine nematode is *Bursaphelenchus xylophilus* (pine wood nematode); the ring nematode is from the genera *Criconema*, *Criconemella*, *Criconemoides*, or *Mesocriconema*; the bulb nematode is *Ditylenchus destructor* (rotten stem nematode), *Ditylenchus dipsaci* (sweet potato stem nematode), or *Ditylenchus* (mushroom stem nematode). Myceliophagus); the trypanosome is a member of the genus *Dolichodorus*; the spiral nematode is either *Helicotylenchus dihystera* or *Helicotylenchus multicintus*; the sheath nematode is either a member of the genus *Hemicycliophora* or *Hemicriconemoides*; the crown nematode is *Hoploaimus columbus*.The pseudo-root-nodule nematode is *Nacobbus aberrans*; the needle nematode is *Longidoruse longatus*; the nail nematode is *Paratylenchus*; the root-rot nematode is *Pratylenchus brachyurus*, *Pratylenchus coffee*, *Pratylenchus zeae*, or *Pratylenchus penetrans*; the perforating nematode is *Radopholus similis*; the kidney-shaped nematode is *Rotylenchus rodus*; the residual root nematode is *Trichodorus primitivus*; and the dwarfing nematode is *Tylenchorhynchus*. The citrus nematode is *Tylenchorhynchus dubius*, or *Tylenchorhynchus dubius*. The citrus nematode is *Tylenchulus semipenetrans*. The xiphine nematode is *Xiphinema americanum*, *Xiphinema index*, or *Xiphinema diversicaudatum*.

8. The method as described in claim 7, characterized in that, The nematode in question is either the southern root-knot nematode (Meloidogyneincognita) or the pine wood nematode (Bursaphelenchus xylophilus).

9. The method as described in claim 5, characterized in that, The plants are selected from: grain crops, vegetables, forest trees, tobacco, citrus, and banana trees.

10. The method as described in claim 9, characterized in that, The grain crops are peanuts, rice, soybeans, sorghum, wheat, or potatoes; the vegetables are cucumbers, tomatoes, spinach, cabbage, or beets; and the trees are poplars, pine trees, cypress trees, or coconut trees.

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