Compound containing synene fragment, application of compound, pesticide for preventing and controlling nematodes and fungi, and method for preventing and controlling nematodes and fungi

Abstract

The invention relates to the field of novel pesticide compounds, and discloses a compound containing a synene fragment and application thereof, a pesticide for preventing and controlling nematodes and / or fungi, and a method for preventing and controlling nematodes and / or fungi. The compound has a structure as shown in a formula (I). The compound containing the synene fragment, provided by the invention, has excellent biological activity on at least one plant parasitic nematode and / or fungus included in the synene fragment at a low dosage. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the field of new pesticide compounds, and in particular to compounds containing synephene fragments and applications thereof, pesticides for controlling nematodes and fungi, and methods for controlling nematodes and fungi. Background Art

[0002] 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.

[0003] Therefore, it is necessary to develop nematicides with higher activity, lower dosage and environmental friendliness to control the harm of nematodes.

[0004] At present, there are literatures that have reported that carboxamide derivatives are used for controlling nematode diseases, such as WO2007 / 108483A1, WO2014 / 177582A1, WO2013 / 076230A1, WO2015 / 007626A1, etc., all of which involve aromatic carboxamides and heteroaromatic carboxamides, showing good activity in killing pests, especially nematodes.

[0005] However, there are still few agents available for the prevention and treatment of 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 treatment of nematode diseases.

[0006] In addition, plant pathogenic fungi are also a major factor that harms crops in agriculture and horticulture. Infection by pathogenic fungi and harmful organisms such as nematodes can lead to a decline in crop quality and a significant drop in yield, causing huge economic losses to producers. Currently, there are few agents that can be used to simultaneously control plant pathogenic fungi and nematodes, so new agents need to be developed to solve this problem. Summary of the invention

[0007] One of the objects of the present invention is to provide a novel compound capable of controlling plant parasitic nematodes.

[0008] The second object of the present invention is to provide a new compound capable of resisting fungi.

[0009] The third object of the present invention is to provide a novel compound which can simultaneously control plant parasitic nematodes and fight fungi.

[0010] In order to achieve the above object, the first aspect of the present invention provides a compound containing a synephine fragment, wherein the compound has a structure shown in formula (I):

[0011]

[0012] Wherein, in formula (I),

[0013] Wherein, in formula (I),

[0014] 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;

[0015] R 4 and R 5 are each independently selected from H, halogen, C 1-6 The alkyl group;

[0016] X 7 is CH or N;

[0017] 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), X 1 , X 2 , X 3 are each independently CH or N; X 4 O, S or NR 7 , X 5 , X 6 and X 10 are each independently CH or N; X 8 and X 9 Each is independently S or O; 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;

[0018] R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group;

[0019] R7 Selected from H, C 1-6 of alkyl.

[0020] The second aspect of the present invention provides the use of the compound containing the synephene fragment described in the first aspect in controlling nematodes and / or antifungals.

[0021] The third aspect of the present invention provides a pesticide for controlling nematodes and / or antifungals, the pesticide containing an effective amount of active ingredients for controlling nematodes and / or antifungals, wherein the active ingredients include at least one of the compounds containing synechocene fragments described in the first aspect.

[0022] 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.

[0023] At least some of the compounds containing synephene fragments provided by the present invention can have excellent inhibitory activity against plant parasitic nematodes at low doses (below 50 mg / L, below 6.25 mg / L, or even lower concentrations).

[0024] For example, at least some of the compounds of the present invention, at a concentration of 50 mg / L, can cause a mortality rate of >80% for second-instar southern root-knot nematodes after 48 hours of treatment with the second-instar southern root-knot nematodes; after rescreening, it was found that the compounds of the present invention can still show a protective effect of >80% against second-instar southern root-knot nematodes at a concentration of 6.25 mg / L or even lower, and have excellent nematicidal activity.

[0025] For another example, at least some of the compounds containing the synephene fragments provided by the present invention can have excellent inhibitory activity against diseases such as wheat stem rot, wheat gibberella, cucumber gray mold, and rapeseed sclerotia at low doses (25 mg / L, below 6.25 mg / L, or even lower concentrations).

[0026] For another example, at least some of the compounds of the present invention exhibited a protective effect of >80% against wheat stem rot, wheat fusarium sphaeroides, 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 could still exhibit a protective effect of >80% against wheat stem rot, wheat fusarium sphaeroides, cucumber gray mold, and rapeseed sclerotinia at a concentration of 6.25 mg / L or even lower, and had excellent fungicidal activity. DETAILED DESCRIPTION

[0027] The endpoints and any values ​​of the ranges disclosed in this article 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 endpoint values ​​of each range, the endpoint values ​​of each range and the 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 as specifically disclosed in this article.

[0028] The following is an explanation of some terms in the present invention.

[0029] 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).

[0030] The halogens described in the present invention include fluorine, chlorine, bromine and iodine.

[0031] 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.

[0032] The present invention's "C 1-6 "Alkyl" means an alkyl group having 1 to 6 carbon atoms (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 that the total number of carbon atoms is different.

[0033] The present invention refers to a "C 1-6 "Alkyl" means C 1-6 At least one H atom on the alkyl group is replaced by a halogen. 1-6 The alkyl group is the same as defined above. 1-4 The term "alkyl" has a similar definition except that the total number of carbon atoms is different.

[0034] "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 in the formula (a) represents a straight or branched alkoxy group having a total carbon number of 1 to 6, for example, the number of carbon atoms may be 1, 2, 3, 4, 5, or 6, including but not limited to methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, n-hexoxy, and the like. 1-4 The term "alkoxy" has a similar definition except for the total number of carbon atoms.

[0035] 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):

[0036]

[0037] Wherein, in formula (I),

[0038] 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;

[0039] R 4 and R 5 are each independently selected from H, halogen, C 1-6 The alkyl group;

[0040] X 7 is CH or N;

[0041] 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), X 1 , X 2 , X 3 are each independently CH or N; X 4 O, S or NR 7 , X 5 , X 6 and X 10 are each independently CH or N; X 8 and X 9 Each is independently S or O; 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 -R6 At least one of;

[0042] R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group;

[0043] R 7 Selected from H, C 1-6 of alkyl.

[0044] According to a preferred specific embodiment (hereinafter referred to as preferred specific embodiment 1), the compound has a structure shown in formula (I):

[0045]

[0046] Wherein, in formula (I),

[0047] 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;

[0048] R 4 and R 5 are each independently selected from H, halogen, C 1-6 The alkyl group;

[0049] X 7 is C;

[0050] A is a group represented by formula (I-2); in formula (I-2), X 4 O, S or NR 7 , X 5 , X 6 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, -SR6 、-S(O)-R 6 、-S(O) 2 -R 6 At least one of;

[0051] R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group;

[0052] R 7 Selected from H, C 1-6 of alkyl.

[0053] In the preferred embodiment 1, more preferably, R 3 Does not exist and X 7 For CH.

[0054] In preferred embodiment 1, further preferably, in formula (I),

[0055] R 1 , R 2 are each independently selected from H, halogen, C 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 Not at the same time H;

[0056] R 4 and R 5 are each independently selected from H, halogen, C 1-6 The alkyl group;

[0057] R 3 Does not exist and X 7 for CH;

[0058] A is a group represented by formula (I-2); in formula (I-2), X 4 O, S or NR 7 , X 5 , X 6 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 1-6Alkoxy, nitro, cyano, -SR 6 、-S(O)-R 6 、-S(O) 2 -R 6 At least one of;

[0059] R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group;

[0060] R 7 Selected from H, C 1-6 of alkyl.

[0061] According to a preferred embodiment (hereinafter referred to as preferred embodiment 2), in formula (I),

[0062] 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;

[0063] R 4 and R 5 are each independently selected from H, halogen, C 1-4 The alkyl group;

[0064] X 7 is CH or N;

[0065] 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), X 1 , X 2 , X 3 are each independently CH or N; X 4 O, S or NR 7 , X 5 , X 6 and X 10 are each independently CH or N; X 8 and X 9Each is independently S or O; 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;

[0066] R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group;

[0067] R 7 Selected from H, C 1-6 of alkyl.

[0068] In preferred embodiment 2, more preferably, in formula (I),

[0069] 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;

[0070] R 4 and R 5 are each independently selected from H, halogen, C 1-4 The alkyl group;

[0071] X 7 is C;

[0072] A is a group represented by formula (I-2); in formula (I-2), X 4 O, S or NR 7 , X 5 , X 6 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;

[0073] R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group;

[0074] R 7 Selected from H, C 1-6 of alkyl.

[0075] In the preferred embodiment 2, further preferably, R 3 Does not exist and X 7 For CH.

[0076] In preferred embodiment 2, it is particularly preferred that in formula (I),

[0077] R 1 , R 2 are each independently selected from H, halogen, C 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 Not at the same time H;

[0078] R 4 and R 5 are each independently selected from H, halogen, C 1-4 The alkyl group;

[0079] R 3 Does not exist and X 7 for CH;

[0080] A is a group represented by formula (I-2); in formula (I-2), X 4 O, S or NR 7 , X 5 , X 6 and X10 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;

[0081] R 6 Selected from C 1-6 Alkyl, C substituted by at least one halogen 1-6 The alkyl group;

[0082] R 7 Selected from H, C 1-6 of alkyl.

[0083] According to a preferred embodiment (hereinafter referred to as preferred embodiment 3), in formula (I),

[0084] 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;

[0085] R 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl;

[0086] X 7 is CH or N;

[0087] 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), X 1 , X 2 , X 3 are each independently CH or N; X 4 O, S or NR 7 , X5 , X 6 and X 10 are each independently CH or N; X 8 and X 9 each independently represents S or O; 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;

[0088] R 6 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy;

[0089] X 7 It is CH or N.

[0090] In the preferred embodiment 3, more preferably, R 7 Selected from H, C 1-6 of alkyl.

[0091] In preferred embodiment 3, more preferably, in formula (I),

[0092] 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;

[0093] R 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl;

[0094] X 7 is C;

[0095] A is a group represented by formula (I-2); in formula (I-2), X 4 O, S or NR 7 , X 5 , X 6 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;

[0096] R 6 is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy;

[0097] R 7 Selected from H, C 1-6 of alkyl.

[0098] In the preferred embodiment 3, further preferably, R 3 Does not exist and X 7 For CH.

[0099] In preferred embodiment 3, further preferably, in formula (I),

[0100] R 1 , R 2 Each independently selected from H, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoromethoxy, -OR 8 ; R 8 is a phenyl group substituted by at least one halogen selected from fluorine, chlorine, bromine and iodine; and R 1 , R 2 Not at the same time H;

[0101] R 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl;

[0102] R 3 Does not exist and X 7for CH;

[0103] A is a group represented by formula (I-2); in formula (I-2), X 4 O, S or NR 7 , X 5 , X 6 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;

[0104] R 6 Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy.

[0105] In preferred embodiment 3, it is particularly preferred that in formula (I),

[0106] R 1 , R 2 Each independently selected from fluorine, chlorine, bromine, iodine, trifluoromethyl;

[0107] R 4 and R 5 Each is independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl;

[0108] R 3 Does not exist and X 7 for CH;

[0109] A is a group represented by formula (I-2); in formula (I-2), X 4 O, S or NR 7 , X 5 , X 6 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 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;

[0110] R 7 It is H or methyl.

[0111] In preferred embodiment 3, most preferably, n is 0, 1, 2 or 3.

[0112] More preferably, the compound represented by formula (I) is selected from any one of the following:

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] 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 in combination with known knowledge in the field of pesticide organic synthesis.

[0119] Illustratively, the present invention provides the following method for preparing the compound described in the first aspect, the method comprising:

[0120]

[0121] Synthesis of intermediate II-A:

[0122] Ultra-dry THF (tetrahydrofuran) is added to alkyl triphenylphosphine bromide, potassium tert-butoxide is added in an ice-water bath, and the reaction is carried out at 0-25° C. for 5-60 minutes. Various substituted ketones are added in an ice-water bath, and the temperature is raised to room temperature after the addition is complete. After 1-5 hours, TLC monitors the reaction to determine whether it is complete. Water is added to quench the reaction, and then extraction, washing, drying, filtration, desolventization, separation and purification are performed to obtain intermediate II-A.

[0123] Synthesis of intermediate III-A:

[0124] The intermediate II-A is dissolved in chloroform, N-bromosuccinimide and p-toluenesulfonic acid are added, and the mixture is heated to reflux. The reaction is monitored by TLC. After the reaction is completed, the heating is stopped, water is added to quench the reaction, and then the mixture is extracted, washed, dried, filtered and desolvated to obtain the intermediate III-A.

[0125] Synthesis of intermediate IV-A:

[0126] The intermediate III-A is dissolved in N,N-dimethylformamide, potassium phthalimide is added at 0-40°C, and the reaction is carried out at 0-40°C for 5 hours. After the reaction is completed as monitored by TLC, ice water is added to the system to precipitate solids from the system, and a filter cake is obtained by suction filtration. The filter cake is recrystallized with petroleum ether and ethyl acetate to obtain the intermediate IV-A.

[0127] Synthesis of intermediate VA:

[0128] The intermediate IV-A is dissolved in ethanol, hydrazine hydrate is added, and the mixture is heated under reflux for 3-5 hours. A white solid is precipitated in the system. After the reaction is completed as monitored by TLC, the heating is stopped, the system is cooled to -10°C to 0°C, and the filtrate is obtained by suction filtration. The filtrate is then extracted, washed, dried, and desolventized to obtain the intermediate VA (wherein R 4 and R 5 Each independently selected from H, C 1-6 of alkyl).

[0129] Synthesis of compounds of formula (I):

[0130] The intermediate VA is dissolved in acetonitrile, and different carboxylic acids, N-methylimidazole and N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate are added under ice bath. After the reaction is completed by TLC monitoring, extraction, washing, separation and purification are performed to obtain the target compound, i.e., the compound of formula (I).

[0131] Illustratively, the present invention also provides the following method for preparing the compound described in the first aspect, the method comprising:

[0132]

[0133] Synthesis of intermediate II-B:

[0134] Dichloromethane is added to various substituted acetophenones, and triphenylphosphine and bromotrichloromethane are added under an ice-water bath. The reaction is complete after monitoring by TLC, and water is added to quench the reaction. The reaction is then extracted, washed, dried, filtered, desolventized, separated and purified to obtain intermediate II-B.

[0135] Synthesis of intermediate III-B:

[0136] The intermediate II-B is dissolved in chloroform, N-bromosuccinimide and p-toluenesulfonic acid are added, and the mixture is heated to reflux. The reaction is monitored by TLC. After the reaction is completed, the heating is stopped, water is added to quench the reaction, and then the mixture is extracted, washed, dried, filtered and desolvated to obtain the intermediate III-B.

[0137] Synthesis of intermediate IV-B:

[0138] The intermediate III-B is dissolved in N,N-dimethylformamide, potassium phthalimide is added at 0-40°C, and the reaction is carried out at 0-40°C for 5 hours. After the reaction is completed as monitored by TLC, ice water is added to the system to precipitate solids from the system, and a filter cake is obtained by suction filtration. The filter cake is recrystallized with petroleum ether and ethyl acetate to obtain intermediate IV-B.

[0139] Synthesis of intermediate VB:

[0140] The intermediate IV-B is dissolved in ethanol, hydrazine hydrate is added, and the mixture is heated under reflux for 3-5 hours. A white solid precipitates out of the system. After the reaction is completed as monitored by TLC, the heating is stopped, the system is cooled to -10°C to 0°C, and the filtrate is obtained by suction filtration. The filtrate is then extracted, washed, dried, and desolventized to obtain the intermediate VB.

[0141] Synthesis of compounds of formula (I):

[0142] The intermediate VB is dissolved in acetonitrile, and different carboxylic acids, N-methylimidazole and N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate are added under ice bath. After the reaction is completed by TLC monitoring, extraction, washing, separation and purification are performed to obtain the target compound, i.e., the compound of formula (I).

[0143] Illustratively, the present invention also provides the following method for preparing the compound described in the first aspect, the method comprising:

[0144]

[0145] Synthesis of intermediate II-C:

[0146] Ultra-dry THF (tetrahydrofuran) is added to methyltriphenylphosphine bromide, and potassium tert-butoxide is added in an ice-water bath. After reacting at 0-25° C. for 5-60 minutes, 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, TLC monitors the reaction to determine whether it is complete. Water is added to quench the reaction, and then extraction, washing, drying, filtration, desolventization, separation and purification are performed to obtain intermediate II-C.

[0147] Synthesis of intermediate III-C:

[0148] The intermediate II-C is dissolved in chloroform, N-bromosuccinimide and p-toluenesulfonic acid are added, and the mixture is heated to reflux. The reaction is monitored by TLC. After the reaction is completed, the heating is stopped, water is added to quench the reaction, and then the mixture is extracted, washed, dried, filtered and desolvated to obtain the intermediate III-C.

[0149] Synthesis of intermediate IV-C:

[0150] The intermediate III-C is dissolved in N,N-dimethylformamide, potassium phthalimide is added at 0-40°C, and the reaction is carried out at 0-40°C for 5 hours. After the reaction is completed as monitored by TLC, ice water is added to the system to precipitate solids from the system, and a filter cake is obtained by suction filtration. The filter cake is recrystallized with petroleum ether and ethyl acetate to obtain the intermediate IV-C.

[0151] Synthesis of intermediate VC:

[0152] The intermediate IV-C is dissolved in ethanol, hydrazine hydrate is added, and the mixture is heated under reflux for 3-5 hours. A white solid precipitates out of the system. After the reaction is completed as monitored by TLC, the heating is stopped, the system is cooled to -10°C to 0°C, and the filtrate is obtained by suction filtration. The filtrate is then extracted, washed, dried, and desolventized to obtain the intermediate VC.

[0153] Synthesis of compounds of formula (I):

[0154] The intermediate VC is dissolved in acetonitrile, and different carboxylic acids, N-methylimidazole and N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate are added under ice bath. After the reaction is completed by TLC monitoring, extraction, washing, separation and purification are performed to obtain the target compound, i.e., the compound of formula (I).

[0155] 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 below the present invention. The present invention will not go into details herein, and those skilled in the art should not interpret this as a limitation on the present invention.

[0156] As mentioned above, the second aspect of the present invention provides the use of the compound containing the synephene fragment described in the first aspect in controlling nematodes and / or antifungal.

[0157] Preferably, the nematode is a plant parasitic nematode.

[0158] Preferably, the nematode is selected from at least one of southern root-knot nematode, peanut root-knot nematode, Java 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 root-knot nematode species; soybean cyst nematode, beet cyst nematode, and other Heterodera species.

[0159] Preferably, the fungus is selected from at least one of wheat fusarium rust, cucumber gray mold, rapeseed sclerotinia, wheat stem rot, wheat powdery mildew, and cucumber powdery mildew.

[0160] As described above, the third aspect of the present invention provides a pesticide for controlling nematodes and / or antifungals, the pesticide containing an effective amount of active ingredients for controlling nematodes and / or antifungals, wherein the active ingredient includes at least one of the compounds containing synechocene fragments described in the first aspect.

[0161] Preferably, the pesticide contains 0.1-99.99wt% of the active ingredient. Exemplarily, in the pesticide, the content of the compound is 1wt%, 5wt%, 10wt%, 15wt%, 20wt%, 25wt%, 30wt%, 35wt%, 40wt%, 45wt%, 50wt%, 55wt%, 60wt%, 65wt%, 70wt%, 75wt%, 80wt%, 85wt%, 90wt%, 95wt%.

[0162] Preferably, the pesticide is in a dosage form selected from at least one of emulsifiable concentrates, suspensions, wettable powders, dusts, granules, aqueous solutions, mother solutions and mother powders.

[0163] As mentioned above, 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 described in the third aspect of the present invention.

[0164] Preferably, the crops are selected from at least one of melons, solanaceous fruits, beans, cereals, and vegetable crops.

[0165] More preferably, the crop is 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.

[0166] The present invention will be described in detail below by way of examples. In the following examples, unless otherwise specified, the raw materials used are all common commercially available products.

[0167] Unless otherwise specified, the room temperature or normal temperature referred to in the present invention means 25±2°C.

[0168] Example 1: Preparation of Compound 1

[0169]

[0170] (1) Take methyltriphenylphosphonium bromide (75 mmol, 1.5 eq.) in a 250 ml eggplant-shaped bottle, add 100 ml of ultra-dry THF, add potassium tert-butoxide (75 mmol, 1.5 eq.) in an ice-water bath, react at room temperature for 20 min, add 2,4-dichloroacetophenone (50 mmol, 1 eq.) in an ice-water bath, and heat to room temperature after the addition is complete. After 2 h, TLC monitors the reaction completion, add water to quench, extract with ethyl acetate, and then wash with water and saturated brine three times, respectively, dry with anhydrous sodium sulfate, and filter to remove solvent to obtain a crude product. The crude product is separated and purified by silica gel column chromatography to obtain intermediate 1 as a colorless oily liquid.

[0171]

[0172] (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, it was extracted with dichloromethane and water, and then washed with saturated brine three times. After drying over anhydrous sodium sulfate, the solvent was removed to obtain yellow oily liquid intermediate 2.

[0173]

[0174] (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 mixture was reacted for 5 h at room temperature. 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 suction filtration. The filter cake was recrystallized with petroleum ether and ethyl acetate to obtain white solid intermediate 3.

[0175]

[0176] (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, the 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 for 3 times, respectively, and dried over anhydrous sodium sulfate. The yellow oily liquid intermediate 4 was obtained by desolventizing.

[0177]

[0178] (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 bath. After the reaction was completed by TLC monitoring, the mixture was extracted with ethyl acetate, washed with water and saturated brine three times respectively, mixed with silica gel and separated by column chromatography to obtain white solid compound 1.

[0179] Example 2: Preparation of Compound 346

[0180]

[0181] (1) Take methyltriphenylphosphonium bromide (75 mmol, 1.5 eq.) in a 250 ml eggplant-shaped bottle, add 100 ml of ultra-dry THF, add potassium tert-butoxide (75 mmol, 1.5 eq.) in an ice-water bath, react at room temperature for 20 min, add 1-(3,5-dichloropyridin-2-yl)ethanone (50 mmol, 1 eq.) in an ice-water bath, and heat to room temperature after the addition is complete. After 2 h, TLC monitors the reaction completion, add water to quench, extract with ethyl acetate, and then wash with water and saturated brine three times, respectively, dry with anhydrous sodium sulfate, and filter to remove solvent to obtain a crude product. The crude product is separated and purified by silica gel column chromatography to obtain intermediate 1 as a colorless oily liquid.

[0182]

[0183] (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, it was extracted with dichloromethane and water, and then washed with saturated brine three times. After drying over anhydrous sodium sulfate, the solvent was removed to obtain yellow oily liquid intermediate 2.

[0184]

[0185] (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 mixture was reacted for 5 h at room temperature. 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 suction filtration. The filter cake was recrystallized with petroleum ether and ethyl acetate to obtain white solid intermediate 3.

[0186]

[0187] (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, the 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 for 3 times, respectively, and dried over anhydrous sodium sulfate. The yellow oily liquid intermediate 4 was obtained by desolventizing.

[0188]

[0189] (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 bath. After the reaction was completed as monitored by TLC, the mixture was extracted with ethyl acetate, washed three times with water and saturated brine respectively, mixed with silica gel and separated by column chromatography to obtain compound 346 as a white solid.

[0190] Example 3: Preparation of Compound 426

[0191]

[0192] (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 bromochloromethane (150 mmol, 3 eq.) were added under an ice-water bath. The reaction was complete after TLC monitoring. Water was added to quench the reaction, and the reaction was extracted with dichloromethane. The reaction was then washed with water and saturated brine for 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.

[0193]

[0194] (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, it was extracted with dichloromethane and water, and then washed with saturated brine three times. After drying over anhydrous sodium sulfate, the solvent was removed to obtain yellow oily liquid intermediate 2.

[0195]

[0196] (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 mixture was reacted for 5 h at room temperature. 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 suction filtration. The filter cake was recrystallized with petroleum ether and ethyl acetate to obtain white solid intermediate 3.

[0197]

[0198] (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, the 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 for 3 times, respectively, and dried over anhydrous sodium sulfate. The yellow oily liquid intermediate 4 was obtained by desolventizing.

[0199]

[0200] (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 bath. After the reaction was completed as monitored by TLC, the mixture was extracted with ethyl acetate, washed three times with water and saturated brine respectively, mixed with silica gel and separated by column chromatography to obtain white solid compound 426.

[0201] The synephine compounds 24 to 65, compounds 89 to 130, compounds 154 to 195, compounds 219 to 260, compounds 279 to 300, compounds 319 to 340, compound 345, compound 448, compound 451 and compound 454 of the present invention are all prepared according to a process similar to 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.

[0202] The dichloroolefin compound 430, compound 435, compound 440 and compound 445 of the present invention are all prepared according to a process similar to that of compound 426, except that the 2,4-dichloroacetophenone in step (1) and the 2-(trifluoromethyl)nicotinic acid in step (5) are replaced by corresponding ketones and carboxylic acids according to the structure of the target compound.

[0203] The characterization data of some specific compounds of the present invention are shown in Table 1.

[0204] Table 1

[0205]

[0206]

[0207]

[0208]

[0209] Comparative Example 1

[0210] Compound CN-1 was prepared according to the method disclosed in CN113845480A. Through experimental studies, it was found that the compound at a concentration of 50 mg / L had a mortality rate of <20% after 48 hours of treatment with second-instar southern root-knot nematodes, and showed almost no protective effect against nematodes.

[0211]

[0212] Test Example 1: Control Effect on Southern Root-Knot Nematodes

[0213] Dissolve the test compound in dimethyl sulfoxide to prepare a 10000 mg / L stock solution, dilute it according to the concentration required for the test, and all agents are prepared for use. Select the southern second-instar larvae (J2) with good growth status for experimental testing. 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 the second-instar larvae of the southern root-knot nematode (about 50 J2), and repeat three times. Investigate the mortality of J2 under a microscope 72 hours after the agent treatment. Calculate the mortality rate and corrected mortality rate.

[0214] The control effects are shown in Table 2.

[0215] Table 2

[0216]

[0217]

[0218] 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%.

[0219] Test Example 2: Control effect on wheat stem rot pathogen

[0220] The compound to be tested was dissolved and diluted with dimethyl sulfoxide to prepare a mother solution. The mycelium growth rate method was used to determine the inhibitory effect of the agent on the mycelium growth of wheat stem rot pathogens. A bacterial disc with a diameter of 5 mm was taken from the edge of the colony after continuous transfer culture for 4 days, and the bacterial disc was inoculated on a PDA plate containing a concentration of 25μg / mL and 6.25μg / mL of the agent, respectively, with 3 replicates for each treatment. All culture dishes were placed in a sterile incubator at 25°C for culture. When the blank control bacteria grew to two-thirds of the diameter of the culture dish, the cross method was used to determine the colony diameter of the control and treatment and calculate the mycelium growth inhibition rate.

[0221] The control effects are shown in Table 3.

[0222] Table 3

[0223]

[0224]

[0225] 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%.

[0226] Test Example 3: Control Effect on Wheat Fusarium Pathogen

[0227] The compound to be tested was dissolved and diluted with dimethyl sulfoxide to prepare a mother solution. The mycelium growth rate method was used to determine the inhibitory effect of the agent on the mycelium growth of wheat fusarium. A bacterial disc with a diameter of 5 mm was taken from the edge of the colony after continuous transfer culture for 4 days, and the bacterial disc was inoculated on a PDA plate containing a concentration of 25μg / mL and 6.25μg / mL of the agent, respectively, with 3 replicates for each treatment. All culture dishes were placed in a sterile incubator at 25°C for culture. When the blank control bacteria grew to two-thirds of the diameter of the culture dish, the cross method was used to determine the colony diameter of the control and treatment and calculate the mycelium growth inhibition rate.

[0228] The control effects are shown in Table 4.

[0229] Table 4

[0230] Compound No. 25μg / mL control effect (%) 6.25μg / mL control effect (%) 25 A A 26 A A 27 A A 28 A A 29 A A 42 A A 45 A B 47 A B 49 A A 51 A A 52 A A 53 A A 56 A A 63 A A 65 A A 182 A A 220 A A 221 A A 222 A A 223 A A 224 A A 240 A A Fluopyram B C

[0231] 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%.

[0232] Test Example 4: Control effect on rapeseed sclerotinia

[0233] The compound to be tested was dissolved and diluted with dimethyl sulfoxide to prepare a mother solution. The mycelium growth rate method was used to determine the inhibitory effect of the agent on the mycelium growth of rapeseed sclerotinia. A bacterial disc with a diameter of 5 mm was taken from the edge of the colony after continuous transfer culture for 4 days, and the bacterial disc was inoculated on a PDA plate containing a concentration of 25μg / mL and 6.25μg / mL of the agent, respectively, with 3 replicates for each treatment. All culture dishes were placed in a sterile incubator at 25°C for culture. When the blank control bacteria grew to two-thirds of the diameter of the culture dish, the cross method was used to determine the colony diameter of the control and treatment and calculate the mycelium growth inhibition rate.

[0234] The control effects are shown in Table 5.

[0235] Table 5

[0236] Compound No. 25μg / mL control effect (%) 6.25μg / mL control effect (%) 26 A A 28 A A 29 A A 31 A B 32 A A 33 A A 35 A A 42 A A 45 A A 49 A A 51 A A 52 A A 63 A A 159 A B 163 A A 182 A B 221 A A 222 A A 223 A B 224 A A 237 A A 240 A A Fluopyram A A

[0237] 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%.

[0238] 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 gibberella, wheat stem rot, and rapeseed sclerotia.

[0239] The preferred embodiments of the present invention are described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, the technical solution of the present invention can be subjected to a variety of simple modifications, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be regarded as the contents disclosed by the present invention and belong to the protection scope 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-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 in the A group that can be substituted, 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-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 in the A group that can be substituted, 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-2); in formula (I-2), 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 the group consisting of 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 1, 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.

5. 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:

6. Use of the compound containing a synechocene fragment according to any one of claims 1 to 5 in controlling nematodes and / or antifungal activities.

7. The use according to claim 6, characterized in that: The nematode is a plant parasitic nematode; Preferably, the nematode is selected from at least one of southern root-knot nematode, peanut root-knot nematode, Java 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, soybean cyst nematode and beet cyst nematode.

8. 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 5.

9. The pesticide for controlling nematodes and / or fungi according to claim 8, characterized in that: The pesticide contains 0.1-99.99 wt % of the active ingredient.

10. The pesticide for controlling nematodes and / or fungi according to claim 8 or 9, 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.

11. 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 8 to 10; 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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