Compound containing dendrene fragment and use of compound, pesticide for controlling nematode and fungus, and method for controlling nematode and fungus

Abstract

The present application relates to the field of novel pesticide compounds, and discloses a compound containing a dendrene fragment and a use of the compound, a pesticide for controlling a nematode and / or fungus, and a method for controlling a nematode and / or fungus. The compound has a structure as shown in formula (I). The compound containing a dendrene fragment can have excellent biological activity against at least one plant parasitic nematode and / or fungus at a low dosage.

Description

Compound containing synephene fragment and application thereof, pesticide for controlling nematodes and fungi, and method for controlling nematodes and fungi

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Chinese patent application No. 202310949090.8 filed on July 31, 2023, the contents of which are incorporated herein by reference. Technical Field

[0003] The present invention relates to the field of new pesticide compounds, and in particular to compounds containing synechocene fragments and applications thereof, pesticides for controlling nematodes and fungi, and methods for controlling nematodes and fungi. Background Art

[0004] In crop production fields such as agriculture and horticulture, nematodes can cause serious damage to plant roots, leading to significant losses of agricultural products and cash crops.

[0005] Therefore, it is necessary to develop nematicides with high activity, low dosage and environmental friendliness to control the damage of nematodes.

[0006] Currently, there are reports that carboxamide derivatives are used to control nematode diseases. For example, WO2007 / 108483A1, WO2014 / 177582A1, WO2013 / 076230A1, WO2015 / 007626A1, etc. all involve arylcarboxamides and heteroarylcarboxamides, which show good pesticidal activity, especially nematode killing activity.

[0007] However, there are still few agents used to control nematodes, and most traditional nematicides are highly toxic to humans and the environment. There is an urgent need to develop new and highly effective nematicides for the prevention and control of nematode diseases.

[0008] Furthermore, plant pathogens are a significant threat to crops in agriculture and horticulture. Infections by pathogenic fungi and pests like nematodes can lead to reduced crop quality and yields, resulting in significant economic losses for producers. Currently, there are few pesticides that can simultaneously control both plant pathogens and nematodes, nematodes. Therefore, the development of new agents is needed to address this problem.

[0009] Summary of the Invention

[0010] One of the objects of the present invention is to provide a novel compound capable of controlling plant parasitic nematodes.

[0011] The second object of the present invention is to provide a new compound capable of resisting fungi.

[0012] The third object of the present invention is to provide a novel compound that can simultaneously control plant parasitic nematodes and fight fungi.

[0013] In order to achieve the above objectives, the first aspect of the present invention provides a compound containing a synephine fragment, wherein the compound has a structure shown in formula (I):

[0014] Wherein, in formula (I),

[0015] R 1 、R 2 、R 3 are each independently selected from H, halogen, C substituted by at least one halogen 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, -OR 8 , or R 3 Does not exist; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 、R 2 、R 3 Not at the same time H;

[0016] R 4 and R 5 are each independently selected from H, halogen, C 1-6 Alkyl;

[0017] X7 is CH or N;

[0018] A is a group represented by formula (I-1), formula (I-2) or formula (I-3); in formula (I-1), formula (I-2) and formula (I-3), X1, X2, and X3 are each independently CH or N; X4 is O, S or NR 7 , X5, X6 and X 10 Each of them is independently CH or N; X8 and X9 are each independently S or O; n R represents n substituents present at any substitutable position in the A group, and the n substituents are the same or different and are each independently selected from halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, nitro, cyano, -SR 6 、-S(O)-R 6 、-S(O)2-R 6 At least one of;

[0019] R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkyl;

[0020] R7 Selected from H, C 1-6 of alkyl.

[0021] The second aspect of the present invention provides use of the compound containing a synechocene fragment described in the first aspect in controlling nematodes and / or antifungals.

[0022] A third aspect of the present invention provides a pesticide for controlling nematodes and / or fungi, the pesticide containing an active ingredient in an effective amount for controlling nematodes and / or fungi, wherein the active ingredient includes at least one of the compounds containing a synechocene fragment described in the first aspect.

[0023] The fourth aspect of the present invention provides a method for controlling nematodes and / or antifungals, the method comprising: applying a pesticide for controlling nematodes and / or antifungals to crops, wherein the pesticide for controlling nematodes and / or antifungals is the pesticide for controlling nematodes and / or antifungals described in the third aspect of the present invention.

[0024] At least some of the compounds containing synechocene fragments provided by the present invention can have excellent inhibitory activity against plant parasitic nematodes at low doses (less than 50 mg / L, less than 6.25 mg / L, or even lower concentrations).

[0025] For example, at least some of the compounds of the present invention, at a concentration of 50 mg / L, reduced the mortality of second-instar southern root-knot nematodes by >80% after 48 hours of treatment. Rescreening revealed that the compounds of the present invention, at a concentration of 6.25 mg / L or even lower, still exhibited a protective effect of >80% against second-instar southern root-knot nematodes, demonstrating excellent nematicidal activity.

[0026] For example, at least some of the compounds containing synephene fragments provided by the present invention have excellent inhibitory activity against diseases such as wheat stem rot, wheat fusarium, cucumber gray mold, and rapeseed sclerotia at low doses (25 mg / L, 6.25 mg / L or less, or even lower concentrations).

[0027] For example, at least some of the compounds of the present invention exhibited a prevention effect of >80% against wheat stem rot, wheat fusarium spp., cucumber gray mold, and rapeseed sclerotinia at a concentration of 25 mg / L; after rescreening, it was found that the compounds of the present invention still exhibited a prevention effect of >80% against wheat stem rot, wheat fusarium spp., cucumber gray mold, and rapeseed sclerotinia at a concentration of 6.25 mg / L or even lower, and had excellent fungicidal activity. DETAILED DESCRIPTION

[0028] The endpoints of the ranges and any values ​​disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoints of each range, the endpoints of each range and individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered to be specifically disclosed herein.

[0029] The following is an explanation of some terms in the present invention.

[0030] The dotted line in the structural formula indicates that formula (I) can be connected to any position on the six-membered ring of formula (I-1), or formula (I) can be connected to any position on the five-membered ring of formula (I-2).

[0031] The halogens mentioned in the present invention include fluorine, chlorine, bromine and iodine.

[0032] The “phenyl group substituted by at least one halogen” mentioned in the present invention means that at least one H atom on the phenyl group is substituted by a halogen.

[0033] The present invention's "C 1-6 "Alkyl" means an alkyl group with a total carbon number of 1-6 (e.g., 1, 2, 3, 4, 5, 6), including straight-chain alkyl groups and branched-chain alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc. 1-4 The term "alkyl" has a similar definition except for the total number of carbon atoms.

[0034] The present invention refers to a "C substituted by at least one halogen" 1-6 "alkyl" means C 1-6 At least one H atom on the alkyl group is substituted by a halogen, 1-6 The alkyl group is the same as defined above. 1-4 The term "alkyl" has a similar definition except for the total number of carbon atoms.

[0035] "C substituted by at least one halogen 1-6 "Alkoxy" means C 1-6 At least one H atom on the alkoxy group is substituted by halogen. 1-6 The alkoxy group represents a straight or branched alkoxy group with a total carbon number of 1-6, for example, the number of carbon atoms can be 1, 2, 3, 4, 5, 6, including but not limited to methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, n-hexoxy, etc. 1-4 The term "alkoxy" has a similar definition except for the total number of carbon atoms.

[0036] As mentioned above, the first aspect of the present invention provides a compound containing a synephine fragment, which has a structure shown in formula (I).

[0037] According to a preferred embodiment (hereinafter referred to as preferred embodiment 1), the compound has a structure shown in formula (I): wherein, in formula (I), R 1 、R 2 、R 3 are each independently selected from H, halogen, C substituted by at least one halogen 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, -OR 8 , or R 3 Does not exist; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 、R 2 、R 3 H and R are not the same at the same time 4 and R 5 are each independently selected from H, halogen, C 1-6 alkyl; X7 is C; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S, or NR 7 , X5, X6 and X 10 Each is independently CH or N; n R represents n substituents present at any position that can be substituted in the A group, and the n substituents are the same or different and are independently selected from halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, nitro, cyano, -SR 6 、-S(O)-R 6 、-S(O)2-R 6 At least one of R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkyl; R 7 Selected from H, C 1-6 of alkyl.

[0038] In the preferred embodiment 1, more preferably, R 3 Not present and X7 is CH.

[0039] In preferred embodiment 1, further preferably, in formula (I), R 1 、R2 are each independently selected from H, halogen, C substituted by at least one halogen 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, -OR 8 ; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 、R 2 H and R are not the same at the same time 4 and R 5 are each independently selected from H, halogen, C 1-6 Alkyl; R 3 does not exist and X7 is CH; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S, or NR 7 , X5, X6 and X 10 Each is independently CH or N; n R represents n substituents present at any position that can be substituted in the A group, and the n substituents are the same or different and are independently selected from halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, nitro, cyano, -SR 6 、-S(O)-R 6 、-S(O)2-R 6 At least one of R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkyl; R 7 Selected from H, C 1-6 of alkyl.

[0040] According to a preferred embodiment (hereinafter referred to as preferred embodiment 2), in formula (I), R 1 、R 2 、R 3 are each independently selected from H, halogen, C substituted by at least one halogen 1-4 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, -OR 8 , or R 3 Does not exist; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 、R 2 、R 3 H and R are not the same at the same time 4 and R 5are each independently selected from H, halogen, C 1-4 alkyl; X7 is CH or N; A is a group represented by formula (I-1), formula (I-2) or formula (I-3); in formula (I-1), formula (I-2) and formula (I-3), X1, X2, and X3 are each independently CH or N; X4 is O, S or NR 7 , X5, X6 and X 10 Each of them is independently CH or N; X8 and X9 are each independently S or O; n R represents n substituents present at any substitutable position in the A group, and the n substituents are the same or different and are each independently selected from halogen, C 1-4 Alkyl, C 1-4 Alkoxy, C substituted by at least one halogen 1-4 Alkyl, C substituted by at least one halogen 1-4 Alkoxy, nitro, cyano, -SR 6 、-S(O)-R 6 、-S(O)2-R 6 At least one of R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkyl; R 7 Selected from H, C 1-6 of alkyl.

[0041] In preferred embodiment 2, more preferably, in formula (I), R 1 、R 2 、R 3 are each independently selected from H, halogen, C substituted by at least one halogen 1-4 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, -OR 8 , or R 3 Does not exist; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 、R 2 、R 3 H and R are not the same at the same time 4 and R 5 are each independently selected from H, halogen, C 1-4 alkyl; X7 is C; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S, or NR 7 , X5, X6 and X 10Each is independently CH or N; n R represents n substituents present at any position that can be substituted in the A group, and the n substituents are the same or different and are independently selected from halogen, C 1-4 Alkyl, C 1-4 Alkoxy, C substituted by at least one halogen 1-4 Alkyl, C substituted by at least one halogen 1-4 Alkoxy, nitro, cyano, -SR 6 、-S(O)-R 6 、-S(O)2-R 6 At least one of R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkyl; R 7 Selected from H, C 1-6 of alkyl.

[0042] In the preferred embodiment 2, further preferably, R 3 Not present and X7 is CH.

[0043] In the preferred embodiment 2, it is particularly preferred that in formula (I), R 1 、R 2 are each independently selected from H, halogen, C substituted by at least one halogen 1-4 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, -OR 8 ; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 、R 2 H and R are not the same at the same time 4 and R 5 are each independently selected from H, halogen, C 1-4 Alkyl; R 3 does not exist and X7 is CH; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S, or NR 7 , X5, X6 and X 10 Each is independently CH or N; n R represents n substituents present at any position that can be substituted in the A group, and the n substituents are the same or different and are independently selected from halogen, C 1-4 Alkyl, C 1-4 Alkoxy, C substituted by at least one halogen 1-4 Alkyl, C substituted by at least one halogen 1-4 Alkoxy, nitro, cyano, -SR 6、-S(O)-R 6 、-S(O)2-R 6 At least one of R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkyl; R 7 Selected from H, C 1-6 of alkyl.

[0044] According to a preferred embodiment (hereinafter referred to as preferred embodiment 3), in formula (I), R 1 、R 2 、R 3 Each independently selected from H, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoromethoxy, -OR 8 , or R 3 Does not exist; R 8 is a phenyl group substituted by at least one halogen selected from fluorine, chlorine, bromine, and iodine; and R 1 、R 2 、R 3 H and R are not the same at the same time 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; X7 is CH or N; A is a group represented by formula (I-1), formula (I-2) or formula (I-3); in formula (I-1), formula (I-2) and formula (I-3), X1, X2, and X3 are each independently CH or N; X4 is O, S or NR 7 , X5, X6 and X 10 Each is independently CH or N; X8 and X9 are each independently S or O; n R represents n substituents present at any substitutable position in the A group, and the n substituents are the same or different and are each independently selected from fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, nitro, cyano, -S(O)-R 6 、-S(O)2-R 6 At least one of R 6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy; X7 is CH or N.

[0045] In the preferred embodiment 3, more preferably, R 7Selected from H, C 1-6 of alkyl.

[0046] In preferred embodiment 3, more preferably, in formula (I), R 1 、R 2 、R 3 Each independently selected from H, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoromethoxy, -OR 8 , or R 3 Does not exist; R 8 is a phenyl group substituted by at least one halogen selected from fluorine, chlorine, bromine, and iodine; and R 1 、R 2 、R 3 H and R are not the same at the same time 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; X7 is C; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S, or NR 7 , X5, X6 and X 10 each independently represents CH or N; n R represents n substituents present at any substitutable position in the A group, and the n substituents are the same or different and are each independently selected from fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, nitro, cyano, -S(O)-R 6 、-S(O)2-R 6 At least one of R 6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy; R 7 Selected from H, C 1-6 of alkyl.

[0047] In the preferred embodiment 3, further preferably, R 3 Not present and X7 is CH.

[0048] In preferred embodiment 3, further preferably, in formula (I), R 1 、R 2 Each independently selected from H, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoromethoxy, -OR 8, or R 3 Does not exist; R 8 is a phenyl group substituted by at least one halogen selected from fluorine, chlorine, bromine, and iodine; and R 1 、R 2 H and R are not the same at the same time 4 and R 5 R is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; 3 does not exist and X7 is CH; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S, or NR 7 , X5, X6 and X 10 each independently represents CH or N; n R represents n substituents present at any substitutable position in the A group, and the n substituents are the same or different and are each independently selected from fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, nitro, cyano, -S(O)-R 6 、-S(O)2-R 6 At least one of R 6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy; R 7 Selected from H, C 1-6 of alkyl.

[0049] According to a preferred embodiment (hereinafter referred to as preferred embodiment 4), in formula (I), R 1 、R 2 Each is independently selected from fluorine, chlorine, bromine, iodine, trifluoromethyl; R 4 and R 5 R is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; 3does not exist and X7 is CH; A is a group represented by formula (I-1); in formula (I-1), X1, X2, and X3 are each independently CH or N; n Rs represent n substituents present at any substitutable position in the A group, and the n substituents are the same or different and are each independently selected from fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, -S(O)2-R 6 At least one of R 6 Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy.

[0050] In the preferred embodiment 4, more preferably, n is 1 or 2.

[0051] In the present invention, it is further preferred that the compound represented by formula (I) is selected from any one of the following:

[0052] According to a preferred embodiment (hereinafter referred to as preferred embodiment 5), in formula (I), R 1 、R 2 Each is independently selected from fluorine, chlorine, bromine, iodine, trifluoromethyl; R 4 and R 5 R is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; 3 does not exist and X7 is CH; A is a group represented by formula (I-2); in formula (I-2), X4 is O, S or NR 7 , X5, X6 and X 10 Each is independently CH or N; n R represents n substituents present at any substitutable position in the A group, and the n substituents are the same or different and are each independently selected from at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl, and trifluoromethyl; R 7 is H or methyl.

[0053] In the preferred embodiment 5, more preferably, n is 0, 1, 2 or 3.

[0054] In the present invention, it is further preferred that the compound represented by formula (I) is selected from any one of the following:

[0055] In the present invention, it is further preferred that the compound represented by formula (I) is selected from any one of Compound 1 to Compound 19, Compound 24 to Compound 84, Compound 89 to Compound 149, Compound 154 to Compound 214, Compound 219 to Compound 274, Compound 279 to Compound 314, Compound 319 to Compound 345, and Compound 426 to Compound 454.

[0056] The present invention has no particular requirements for the specific method for preparing the compound described in the first aspect. Those skilled in the art can determine a suitable preparation route to obtain the compound described in the first aspect based on the structural formula disclosed in the present invention and combined with known knowledge in the field of pesticide organic synthesis.

[0057] Illustratively, the present invention provides the following method for preparing the compound described in the first aspect, the method comprising:

[0058] Synthesis of Intermediate II-A: Ultra-dry THF (tetrahydrofuran) is added to alkyltriphenylphosphine bromide, followed by potassium tert-butoxide in an ice-water bath. The reaction is carried out at 0-25°C for 5-60 minutes, and various substituted ketones are added in an ice-water bath. After the addition is complete, the temperature is raised to room temperature. After 1-5 hours, the reaction is complete as monitored by TLC. Water is added to quench the reaction, followed by extraction, washing, drying, filtration, desolvation, separation, and purification to obtain Intermediate II-A.

[0059] Synthesis of intermediate III-A: The intermediate II-A was dissolved in chloroform, N-bromosuccinimide and p-toluenesulfonic acid were added, and the mixture was heated to reflux. The reaction was monitored by TLC. After the reaction was completed, the heating was stopped, and water was added to quench the reaction. The mixture was then extracted, washed, dried, filtered, and desolvated to obtain intermediate III-A.

[0060] Synthesis of intermediate IV-A: The intermediate III-A was dissolved in N,N-dimethylformamide, potassium phthalimide was added at 0-40°C, and the reaction was carried out at 0-40°C for 5 hours. After the reaction was completed as monitored by TLC, ice water was added to the system to precipitate a solid. The filter cake was obtained by filtration, and the filter cake was recrystallized with petroleum ether and ethyl acetate to obtain intermediate IV-A.

[0061] Synthesis of intermediate VA: The intermediate IV-A was dissolved in ethanol, hydrazine hydrate was added, and the mixture was heated under reflux for 3-5 hours. A white solid was precipitated in the system. After the reaction was completed by TLC monitoring, the heating was stopped, the system was cooled to -10°C to 0°C, and the filtrate was filtered to obtain the filtrate, which was then extracted, washed, dried, and desolvated to obtain intermediate VA (wherein R4 and R5 are each independently selected from H, C 1-6 of alkyl).

[0062] Synthesis of the compound of formula (I): The intermediate VA is dissolved in acetonitrile, and different carboxylic acids, N-methylimidazole and N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate are added under an ice bath. After the reaction is completed by TLC monitoring, the mixture is extracted, washed, separated and purified to obtain the target compound, i.e., the compound of formula (I).

[0063] Illustratively, the present invention further provides the following method for preparing the compound described in the first aspect, the method comprising:

[0064] Synthesis of Intermediate II-B: Dichloromethane was added to various substituted acetophenones, and triphenylphosphine and bromotrichloromethane were added under an ice-water bath. The reaction was monitored by TLC to be complete, and water was added to quench the reaction. The reaction was then extracted, washed, dried, filtered, desolvated, separated, and purified to obtain Intermediate II-B.

[0065] Synthesis of Intermediate III-B: The intermediate II-B was dissolved in chloroform, N-bromosuccinimide and p-toluenesulfonic acid were added, and the mixture was heated to reflux. The reaction was monitored by TLC. After the reaction was completed, heating was stopped, and water was added to quench the reaction. The mixture was then extracted, washed, dried, and filtered to remove the solvent to obtain Intermediate III-B.

[0066] Synthesis of intermediate IV-B: The intermediate III-B was dissolved in N,N-dimethylformamide, potassium phthalimide was added at 0-40°C, and the reaction was carried out at 0-40°C for 5 hours. After the reaction was completed as monitored by TLC, ice water was added to the system to precipitate solids. The filter cake was obtained by filtration, and the filter cake was recrystallized with petroleum ether and ethyl acetate to obtain intermediate IV-B.

[0067] Synthesis of intermediate VB: The intermediate IV-B was dissolved in ethanol, hydrazine hydrate was added, and the mixture was heated under reflux for 3-5 hours. A white solid precipitated from the system. After the reaction was completed as monitored by TLC, heating was stopped, the system was cooled to -10°C to 0°C, and the filtrate was filtered to obtain the filtrate, which was then extracted, washed, dried, and desolvated to obtain the intermediate VB.

[0068] Synthesis of the compound of formula (I): The intermediate VB is dissolved in acetonitrile, and different carboxylic acids, N-methylimidazole and N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate are added under an ice bath. After the completion of the reaction, the reaction is monitored by TLC, followed by extraction, washing, separation and purification to obtain the target compound, i.e., the compound of formula (I).

[0069] Unless otherwise specified, the present invention has no particular limitation on the conditions and specific operating parameters involved in the aforementioned preparation method. Those skilled in the art may make selections based on the knowledge known in the art, or may make selections based on the parameters and conditions provided in the examples listed later in the present invention. The present invention will not go into details here, and those skilled in the art should not interpret this as a limitation on the present invention.

[0070] As previously mentioned, the second aspect of the present invention provides the use of the compound containing a syntenic fragment described in the first aspect for nematode control and / or antifungal treatment. Preferably, the nematode is a plant-parasitic nematode. More preferably, the nematode is selected from at least one of the following: southern root-knot nematode, peanut root-knot nematode, javanic root-knot nematode, northern root-knot nematode, rice root-knot nematode, cucumber root-knot nematode, tomato root-knot nematode, banana root-knot nematode, tobacco root-knot nematode, watermelon root-knot nematode, pumpkin root-knot nematode, melon root-knot nematode, eggplant root-knot nematode, and other species of root-knot nematode; soybean cyst nematode, beet cyst nematode, and other species of Heterodera. Further preferably, the fungus is selected from at least one of the following: wheat scab, cucumber gray mold, rapeseed sclerotinia, wheat stem rot, wheat powdery mildew, and cucumber powdery mildew.

[0071] As described above, the third aspect of the present invention provides a pesticide for controlling nematodes and / or fungi, comprising an active ingredient in an effective amount for controlling nematodes and / or fungi, wherein the active ingredient comprises at least one of the compounds containing synephene fragments described in the first aspect. Preferably, the pesticide contains 0.1-99.99 wt% of the active ingredient. Exemplarily, the content of the compound in the pesticide is 1 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, 90 wt%, or 95 wt%. Preferably, the pesticide is in a formulation selected from at least one of an emulsifiable concentrate, a suspension concentrate, a wettable powder, a dust, a granule, an aqueous solution, a mother liquor, and a mother powder.

[0072] As previously mentioned, the fourth aspect of the present invention provides a method for controlling nematodes and / or antifungals, comprising applying a nematode and / or antifungal pesticide to crops, wherein the nematode and / or antifungal pesticide is the nematode pesticide described in the third aspect of the present invention. Preferably, the crops are selected from at least one of melons, solanaceous fruits, legumes, cereals, and vegetables. More preferably, the crops are selected from at least one of wheat, cucumber, rapeseed, peanuts, rice, potatoes, radishes, turnips, lettuce, cabbage, grapes, citrus, sugarcane, bananas, pitaya, peppers, celery, citrus, watermelon, and tomatoes.

[0073] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, the raw materials used are common commercial products. Unless otherwise specified, the room temperature or normal temperature referred to in the present invention means 25±2°C.

[0074] Example 1: Preparation of Compound 1

[0075] (1) Methyltriphenylphosphonium bromide (75 mmol, 1.5 eq.) was placed in a 250 ml eggplant-shaped flask, and 100 ml of ultra-dry THF was added. Potassium tert-butoxide (75 mmol, 1.5 eq.) was added in an ice-water bath. After reacting at room temperature for 20 min, 2,4-dichloroacetophenone (50 mmol, 1 eq.) was added in an ice-water bath. After the addition was complete, the temperature was raised to room temperature. After 2 h, TLC was used to monitor the reaction completion. Water was added to quench the reaction, and the mixture was extracted with ethyl acetate. The mixture was washed with water and saturated brine three times, dried over anhydrous sodium sulfate, and filtered to remove the solvent to obtain a crude product. The crude product was separated and purified by silica gel column chromatography to obtain intermediate 1 as a colorless oily liquid.

[0076] (2) Intermediate 1 (40 mmol, 1 eq.) was dissolved in chloroform, and N-bromosuccinimide (NBS, 44 mmol, 1.1 eq.) and p-toluenesulfonic acid (TsOH, 12 mmol, 0.3 eq.) were added. The mixture was heated to reflux at 65°C and the reaction was monitored by TLC. After the reaction was completed, the heating was stopped and water was added to quench the reaction. After the reaction was cooled to room temperature, the mixture was extracted with dichloromethane and water, and then washed with saturated brine three times. The mixture was dried over anhydrous sodium sulfate and desolvated to obtain yellow oily liquid intermediate 2.

[0077] (3) Intermediate 2 (35 mmol, 1 eq.) was dissolved in N,N-dimethylformamide (DMF), and potassium phthalimide (52.5 mmol, 1.5 eq.) was added at room temperature. The reaction was allowed to proceed for 5 h. After the reaction was completed as monitored by TLC, a large amount of ice water was added to the system to precipitate solids. The filter cake was obtained by filtration, and the filter cake was recrystallized with petroleum ether and ethyl acetate to obtain a white solid intermediate 3.

[0078] (4) The above intermediate 3 (20 mmol, 1 eq.) was dissolved in ethanol, and hydrazine hydrate (mass fraction 85%) (40 mmol, 2 eq.) was added. The mixture was heated under reflux for 4 h. A white solid precipitated from the system. After the reaction was completed as monitored by TLC, heating was stopped, the system was cooled to 0°C, and the filtrate was filtered to obtain a filtrate. The filtrate was extracted with ethyl acetate, and then washed with water and saturated brine three times, respectively. The mixture was dried over anhydrous sodium sulfate and desolvated to obtain a yellow oily liquid intermediate 4.

[0079] (5) Intermediate 4 (2 mmol, 1 eq.) was dissolved in acetonitrile, and 2-(trifluoromethyl)nicotinic acid (2.4 mmol, 1.2 eq.), N-methylimidazole (NMI, 7 mmol, 3.5 eq.) and N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate (TCFH, 2.4 mmol, 1.2 eq.) were added under ice-cooling. After completion of the reaction, the mixture was monitored by TLC. The mixture was extracted with ethyl acetate, washed three times with water and saturated brine, respectively, and separated by column chromatography on silica gel to obtain compound 1 as a white solid.

[0080] Example 2: Preparation of Compound 426

[0081] (1) 2,4-Dichloroacetophenone (50 mmol, 1 eq.) was placed in a 250 ml eggplant-shaped flask, and 100 ml of dichloromethane was added. Triphenylphosphine (225 mmol, 4.5 eq.) and bromotrichloromethane (150 mmol, 3 eq.) were added under ice-water bath. The reaction was monitored by TLC to be complete. Water was added to quench the reaction, and the mixture was extracted with dichloromethane. The mixture was washed three times with water and saturated brine, dried over anhydrous sodium sulfate, and filtered to remove the solvent to obtain a crude product. The crude product was separated and purified by silica gel column chromatography to obtain intermediate 1 as a colorless oily liquid.

[0082] (2) Intermediate 1 (40 mmol, 1 eq.) was dissolved in chloroform, and N-bromosuccinimide (NBS, 44 mmol, 1.1 eq.) and p-toluenesulfonic acid (TsOH, 12 mmol, 0.3 eq.) were added. The mixture was heated to reflux at 65°C and the reaction was monitored by TLC. After the reaction was completed, the heating was stopped and water was added to quench the reaction. After the reaction was cooled to room temperature, the mixture was extracted with dichloromethane and water, and then washed with saturated brine three times. The mixture was dried over anhydrous sodium sulfate and desolvated to obtain yellow oily liquid intermediate 2.

[0083] (3) Intermediate 2 (35 mmol, 1 eq.) was dissolved in N,N-dimethylformamide (DMF), and potassium phthalimide (52.5 mmol, 1.5 eq.) was added at room temperature. The reaction was allowed to proceed for 5 h. After the reaction was completed as monitored by TLC, a large amount of ice water was added to the system to precipitate solids. The filter cake was obtained by filtration, and the filter cake was recrystallized with petroleum ether and ethyl acetate to obtain a white solid intermediate 3.

[0084] (4) The above intermediate 3 (20 mmol, 1 eq.) was dissolved in ethanol, and hydrazine hydrate (mass fraction 85%) (40 mmol, 2 eq.) was added. The mixture was heated under reflux for 4 h. A white solid precipitated from the system. After the reaction was completed as monitored by TLC, heating was stopped, the system was cooled to 0°C, and the filtrate was filtered to obtain a filtrate. The filtrate was extracted with ethyl acetate, and then washed with water and saturated brine three times, respectively. The mixture was dried over anhydrous sodium sulfate and desolvated to obtain a yellow oily liquid intermediate 4.

[0085] (5) Intermediate 4 (2 mmol, 1 eq.) was dissolved in acetonitrile, and 2-(trifluoromethyl)nicotinic acid (2.4 mmol, 1.2 eq.), N-methylimidazole (NMI, 7 mmol, 3.5 eq.) and N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate (TCFH, 2.4 mmol, 1.2 eq.) were added under ice-cooling. After completion of the reaction monitored by TLC, the mixture was extracted with ethyl acetate and washed three times with water and saturated brine, respectively. The sample was mixed with silica gel and separated by column chromatography to obtain compound 426 as a white solid.

[0086] Compounds 1 to 19, 24 to 84, 89 to 149, 154 to 214, 219 to 274, 279 to 314, 319 to 345, and 446 to 454 of the present invention are all prepared according to a process similar to that of compound 1, except that the 2,4-dichloroacetophenone and methyltriphenylphosphine bromide in step (1) and the 2-(trifluoromethyl)nicotinic acid in step (5) are replaced by corresponding ketones, phosphorus ylide reagents, and carboxylic acids according to the structure of the target compound.

[0087] Compounds 426 to 445 of the present invention were prepared according to a process similar to that of compound 426, except that 2,4-dichloroacetophenone in step (1) and 2-(trifluoromethyl)nicotinic acid in step (5) were replaced by corresponding ketones and carboxylic acids according to the structures of the target compounds.

[0088] The characterization data of some specific compounds of the present invention are shown in Table 1.

[0089] Table 1

[0090] Comparative Example 1

[0091] Compound CN-1 was prepared according to the method disclosed in CN113845480A. Experimental studies found that at a concentration of 50 mg / L, the compound reduced the mortality rate of second-instar southern root-knot nematodes by less than 20% after 48 hours of treatment, demonstrating little nematode protection.

[0092] Test Example 1: Control Effect on Southern Root-Knot Nematode

[0093] The test compound was dissolved in dimethyl sulfoxide to prepare a 10 g / L stock solution, which was diluted according to the concentration required for the test. All agents were prepared and used fresh. Second-instar larvae (J2) of southern root-knot nematodes with good growth were selected for the test. Prepare a 96-well cell culture plate, add 90 μL of the test agent at a concentration of 50 mg / L, and then add 10 μL of second-instar larvae of southern root-knot nematodes (about 50 J2), and repeat three times. The J2 mortality rate was investigated under a microscope 72 hours after the agent treatment. The mortality rate and the corrected mortality rate were calculated. The control effect is shown in Table 2.

[0094] Table 2

[0095] A, B, C, D, and E represent the levels of protection effectiveness, and 80% ≦ A ≦ 100%; 70% ≦ B < 80%; 60% ≦ C < 70%, 50% ≦ D < 60%; E < 50%.

[0096] Test Example 2: Control Effect on Wheat Stem Rot

[0097] The test compound was dissolved and diluted in dimethyl sulfoxide to prepare a stock solution. The mycelial growth inhibition effect of the agent against wheat stem rot pathogen was determined using the mycelial growth rate method. A 5 mm diameter plate was obtained from the edge of a colony after four days of continuous transfer culture and inoculated onto PDA plates containing 25 μg / mL and 6.25 μg / mL of the agent, respectively, with three replicates for each treatment. All plates were placed in a sterile incubator at 25°C. When the blank control bacteria grew to two-thirds of the plate diameter, the colony diameters of the control and treatment plates were measured using the cross-hatch method, and the mycelial growth inhibition rate was calculated. The control efficacy is shown in Table 3.

[0098] Table 3

[0099] A, B, C, D, and E represent the levels of protection effectiveness, and 80% ≦ A ≦ 100%; 70% ≦ B < 80%; 60% ≦ C < 70%, 50% ≦ D < 60%; E < 50%.

[0100] Test Example 3: Control Effect on Wheat Gibberella

[0101] The test compound was dissolved and diluted in dimethyl sulfoxide to prepare a stock solution. The mycelial growth inhibition effect of the agent against wheat fusarium head blight was determined using the mycelial growth rate method. A 5 mm diameter plate was obtained from the edge of a colony after four days of continuous transfer culture. This plate was inoculated onto PDA plates containing 25 μg / mL and 6.25 μg / mL of the agent, respectively, with three replicates for each treatment. All plates were placed in a sterile incubator at 25°C. When the blank control bacteria grew to two-thirds of the plate diameter, the colony diameters of the control and treatment plates were measured using the cross-hatch method, and the mycelial growth inhibition rate was calculated. The control efficacy is shown in Table 4.

[0102] Table 4

[0103] A, B, C, D, and E represent the levels of protection effectiveness, and 80% ≦ A ≦ 100%; 70% ≦ B < 80%; 60% ≦ C < 70%, 50% ≦ D < 60%; E < 50%.

[0104] Test Example 4: Control Effect on Cucumber Gray Mold

[0105] The test compound was dissolved and diluted in dimethyl sulfoxide to prepare a stock solution. The mycelial growth inhibition effect of the agent against cucumber gray mold was determined using the mycelial growth rate method. 5 mm diameter plates were harvested from the edge of a colony after four days of continuous transfer culture and inoculated onto PDA plates containing 25 μg / mL and 6.25 μg / mL of the agent, respectively, with three replicates per treatment. All plates were placed in a sterile incubator at 25°C for incubation. When the blank control strain grew to two-thirds of the plate diameter, the colony diameters of the control and treatment plates were measured using the cross-hatch method, and the mycelial growth inhibition rate was calculated. The control efficacy is shown in Table 5.

[0106] Table 5

[0107] A, B, C, D, and E represent the levels of protection effectiveness, and 80% ≦ A ≦ 100%; 70% ≦ B < 80%; 60% ≦ C < 70%, 50% ≦ D < 60%; E < 50%.

[0108] Test Example 5: Control Effect on Rapeseed Sclerotinia

[0109] The test compound was dissolved and diluted in dimethyl sulfoxide to prepare a stock solution. The hyphal growth inhibition effect of the agent on Sclerotinia sclerotiorum was determined using the hyphal growth rate method. 5 mm diameter plates were harvested from the edge of a colony after four days of continuous transfer culture and inoculated onto PDA plates containing 25 μg / mL and 6.25 μg / mL of the agent, respectively, with three replicates per treatment. All plates were placed in a sterile incubator at 25°C. When the blank control strain grew to two-thirds of the plate diameter, the colony diameters of the control and treatment plates were measured using the cross-hatch method, and the hyphal growth inhibition rate was calculated. The control efficacy is shown in Table 6.

[0110] Table 6

[0111] A, B, C, D, and E represent the levels of protection effectiveness, and 80% ≦ A ≦ 100%; 70% ≦ B < 80%; 60% ≦ C < 70%, 50% ≦ D < 60%; E < 50%.

[0112] From the above results, it can be seen that the compounds provided by the present invention can have excellent inhibitory activity against plant parasitic nematodes at low doses. At the same time, the compounds of the present invention also have excellent inhibitory activity against pathogens such as wheat fusarium, wheat stem rot, cucumber gray mold, and rapeseed sclerotia.

[0113] The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, various simple variations of the technical solution of the present invention may be made, including combining the various technical features in any other appropriate manner. These simple variations and combinations should also be regarded as disclosed in the present invention and fall within the scope of protection of the present invention.

Claims

1. A compound containing a synephine fragment, characterized in that The compound has a structure shown in formula (I): Wherein, in formula (I), R 1 , R 2 , R 3 are each independently selected from H, halogen, C 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, -OR 8 , or R 3 Does not exist; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 , R 2 , R 3 Not at the same time H; R 4 and R 5 are each independently selected from H, halogen, C 1-6 The alkyl group; X7 is C; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S or NR 7 , X5, X6 and X 10 Each is independently CH or N; n R represents n substituents present at any position that can be substituted in the A group, and the n substituents are the same or different and are independently selected from halogen, C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, nitro, cyano, -SR 6 、-S(O)-R 6 、-S(O)2-R 6 At least one of; R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group; R 7 Selected from H, C 1-6 The alkyl group; Preferably, R 3 Not present and X7 is CH.

2. The compound containing a synechocene fragment according to claim 1, characterized in that In formula (I), R 1 , R 2 , R 3 are each independently selected from H, halogen, C 1-4 Alkyl, C substituted by at least one halogen 1-6 Alkoxy, -OR 8 , or R 3 Does not exist; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 , R 2 , R 3 Not at the same time H; R 4 and R 5 are each independently selected from H, halogen, C 1-4 The alkyl group; X7 is C; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S or NR 7 , X5, X6 and X 10 Each is independently CH or N; n R represents n substituents present at any position that can be substituted in the A group, and the n substituents are the same or different and are independently selected from halogen, C 1-4 Alkyl, C 1-4 Alkoxy, C substituted by at least one halogen 1-4 Alkyl, C substituted by at least one halogen 1-4 Alkoxy, nitro, cyano, -SR 6 、-S(O)-R 6 、-S(O)2-R 6 At least one of; R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group; R 7 Selected from H, C 1-6 The alkyl group; Preferably, R 3 Not present and X7 is CH.

3. The compound containing a synechocene fragment according to claim 1, characterized in that In formula (I), R 1 , R 2 , R 3 Each independently selected from H, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoromethoxy, -OR 8 , or R 3 Does not exist; R 8 is a phenyl group substituted by at least one halogen selected from fluorine, chlorine, bromine and iodine; and R 1 , R 2 , R 3 Not at the same time H; R 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; X7 is C; A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X1, X2, and X3 are each independently CH or N; X4 is O, S or NR 7 , X5, X6 and X 10 each independently represents CH or N; n R represents n substituents present at any position capable of being substituted in the A group, and the n substituents are the same or different and are each independently selected from fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, nitro, cyano, -S(O)-R 6 、-S(O)2-R 6 At least one of; R 6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy; R 7 Selected from H, C 1-6 The alkyl group; Preferably, R 3 Not present and X7 is CH.

4. The compound containing a synechocene fragment according to claim 3, characterized in that In formula (I), R 1 , R 2 Each independently selected from fluorine, chlorine, bromine, iodine, trifluoromethyl; R 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; R 3 does not exist and X7 is CH; A is a group represented by formula (I-1); in formula (I-1), X1, X2, and X3 are each independently CH or N; n Rs represent n substituents present at any position that can be substituted in the A group, and the n substituents are the same or different and are each independently selected from fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, -S(O)2-R 6 At least one of; R 6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy; Preferably, n is 1 or 2; More preferably, the compound represented by formula (I) is selected from any one of the following:

5. The compound containing a synechocene fragment according to claim 3, characterized in that In formula (I), R 1 , R 2 Each independently selected from fluorine, chlorine, bromine, iodine, trifluoromethyl; R 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; R 3 does not exist and X7 is CH; A is a group represented by formula (I-2); in formula (I-2), X4 is O, S or NR 7 , X5, X6 and X 10 Each is independently CH or N; n R represents n substituents present at any position that can be substituted in the A group, and the n substituents are the same or different and are independently selected from at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl and trifluoromethyl; R 7 is H or methyl; Preferably, n is 0, 1, 2 or 3; More preferably, the compound represented by formula (I) is selected from any one of the following:

6. The compound containing a synechocene fragment according to claim 1, characterized in that The compound represented by formula (I) is selected from any one of the following:

7. Use of the compound containing a synechocene fragment according to any one of claims 1 to 6 in controlling nematodes and / or antifungal effects.

8. The use according to claim 7, characterized in that: The nematodes are plant parasitic nematodes; Preferably, the nematode is selected from the group consisting of southern root-knot nematodes, peanut root-knot nematodes, Java root-knot nematodes, northern root-knot nematodes, rice root-knot nematodes, cucumber root-knot nematodes, tomato root-knot nematodes, banana root-knot nematodes, tobacco root-knot nematodes, watermelon root-knot nematodes, pumpkin root-knot nematodes, melon root-knot nematodes, and eggplant root-knot nematodes. At least one of root-knot nematodes, soybean cyst nematodes, and beet cyst nematodes.

9. A pesticide for controlling nematodes and / or antifungals, characterized in that: The pesticide contains an active ingredient in an effective amount for controlling nematodes and / or antifungi, wherein the active ingredient comprises at least one of the compounds containing synechocene fragments according to any one of claims 1 to 6.

10. The pesticide for controlling nematodes and / or fungi according to claim 9, characterized in that: The pesticide contains 0.1-99.99 wt % of the active ingredient.

11. The pesticide for controlling nematodes and / or fungi according to claim 9 or 10, characterized in that: The formulation of the pesticide is selected from at least one of emulsifiable concentrate, suspension, wettable powder, dust, granule, aqueous solution, mother liquor and mother powder.

12. A method for controlling nematodes and / or fungi, characterized in that: The method comprises: applying a pesticide for controlling nematodes and / or antifungals to crops, wherein the pesticide for controlling nematodes and / or antifungals is the pesticide for controlling nematodes and / or antifungals according to any one of claims 9 to 11; Preferably, the crop is selected from at least one of melons, solanaceous fruits, beans, cereals, and vegetable crops; Preferably, the crops are selected from at least one of wheat, cucumber, rapeseed, peanut, rice, potato, radish, carrot, lettuce, cabbage, grape, citrus, sugarcane, banana, pitaya, pepper, celery, citrus, watermelon and tomato.

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