WO2025026281A1 - 含突烯片段的化合物及其应用、用于防治线虫和真菌的农药、防治线虫和真菌的方法 - Google Patents

含突烯片段的化合物及其应用、用于防治线虫和真菌的农药、防治线虫和真菌的方法 Download PDF

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WO2025026281A1
WO2025026281A1 PCT/CN2024/108246 CN2024108246W WO2025026281A1 WO 2025026281 A1 WO2025026281 A1 WO 2025026281A1 CN 2024108246 W CN2024108246 W CN 2024108246W WO 2025026281 A1 WO2025026281 A1 WO 2025026281A1
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formula
halogen
butyl
nematodes
alkyl
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PCT/CN2024/108246
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English (en)
French (fr)
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杨光富
黄远晖
魏阁
张璞
张圆圆
熊姿
姚凯诚
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江苏中旗科技股份有限公司
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Publication of WO2025026281A1 publication Critical patent/WO2025026281A1/zh

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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • 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.
  • nematodes can cause serious damage to plant roots, leading to significant losses of agricultural products and cash crops.
  • 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.
  • 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.
  • 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.
  • One of the objects of the present invention is to provide a novel compound capable of controlling plant parasitic nematodes.
  • the second object of the present invention is to provide a new compound capable of resisting fungi.
  • the third object of the present invention is to provide a novel compound which can simultaneously control plant parasitic nematodes and fight fungi.
  • the first aspect of the present invention provides a compound containing a synephine fragment, wherein the compound has a structure shown in formula (I):
  • R 1 , R 2 , and R 3 are each independently selected from H, halogen, C 1-6 alkyl substituted by at least one halogen, C 1-6 alkoxy substituted by at least one halogen, -OR 8 , or R 3 is absent; R 8 is phenyl or phenyl substituted by at least one halogen; and R 1 , R 2 , and R 3 are not H at the same time;
  • R4 and R5 are each independently selected from H, halogen, C1-6 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 , X3 are each independently CH or N; X4 is O, S or NR7 , X5 , X6 and X10 are each independently CH or N; X8 and X9 are each independently S or O; 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 at least one of halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 alkyl substituted by at least one halogen, C1-6 alkoxy substituted by at least one halogen, nitro, cyano, -SR6 , -S(O) -R6 , and -S(O) 2 - R6 ;
  • R6 is selected from C1-6 alkyl, C1-6 alkyl substituted by at least one halogen
  • R7 is selected from H and C1-6 alkyl.
  • 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.
  • the third aspect of the present invention provides a pesticide for controlling nematodes and/or antifungals, the pesticide containing an active ingredient in an effective amount 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.
  • 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.
  • 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).
  • the compounds of the present invention 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.
  • 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).
  • 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.
  • 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).
  • halogens described in the present invention include fluorine, chlorine, bromine and iodine.
  • phenyl group substituted by at least one halogen means that at least one H atom on the phenyl group is substituted by a halogen.
  • C 1-6 alkyl refers to an alkyl group with a total carbon atom count of 1-6 (e.g., 1, 2, 3, 4, 5, 6), including a straight-chain alkyl group and a branched-chain alkyl group, such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a n-hexyl group, etc.
  • a "C 1-4 alkyl group” has a similar definition, except that the total carbon atom count is different.
  • C 1-6 alkyl group substituted by at least one halogen means that at least one H atom on the C 1-6 alkyl group is substituted by a halogen, and the C 1-6 alkyl group has the same definition as above.
  • the "C 1-4 alkyl group substituted by at least one halogen” has a similar definition, except that the total number of carbon atoms is different.
  • C 1-6 alkoxy substituted by at least one halogen means that at least one H atom on the C 1-6 alkoxy is substituted by a halogen.
  • C 1-6 alkoxy means a straight or branched alkoxy group having a total carbon atom number of 1-6, for example, the number of carbon atoms may be 1, 2, 3, 4, 5, 6, including but not limited to methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentyloxy, n-hexyloxy, etc.
  • C 1-4 alkoxy substituted by at least one halogen has a similar definition, except that the total number of carbon atoms is different.
  • the first aspect of the present invention provides a compound containing a synephine fragment, wherein the compound has a structure shown in formula (I).
  • the compound has a structure shown in formula (I): wherein in formula (I), R 1 , R 2 , and R 3 are each independently selected from H, halogen, C 1-6 alkyl substituted by at least one halogen, C 1-6 alkoxy substituted by at least one halogen, -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 , and R 3 are not H at the same time; R 4 and R 5 are each independently selected from H, halogen, and C 1-6 alkyl; X 7 is C; A is a group shown in formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X 1 , X 2 , and X 3 are each independently CH or N; X 4 is O, S or NR 7 , and X 5 , X 6 and X 7 are
  • R 3 is absent and X 7 is CH.
  • R 1 and R 2 are each independently selected from H, halogen, C 1-6 alkyl substituted by at least one halogen, C 1-6 alkoxy substituted by at least one halogen, -OR 8 ;
  • R 8 is phenyl or phenyl substituted by at least one halogen; and
  • R 1 and R 2 are not H at the same time;
  • R 4 and R 5 are each independently selected from H, halogen, C 1-6 alkyl;
  • R 3 is absent and X 7 is CH;
  • A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X 1 , X 2 , and X 3 are each independently CH or N;
  • X 4 is O, S or NR 7 , and
  • X 5 , X 6 and X 7 are each independently CH or N;
  • 10 are each independently CH or N;
  • n R represent n substituents present at any substitutable position in the A group,
  • R 1 , R 2 , and R 3 are each independently selected from H, halogen, C 1-4 alkyl substituted by at least one halogen, C 1-6 alkoxy substituted by at least one halogen, -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 , and R 3 are not H at the same time;
  • R 4 and R 5 are each independently selected from H, halogen, and C 1-4 alkyl;
  • X 7 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),
  • X 1 , X 2 , and X 3 are each independently selected from CH or N;
  • X 4 is O, S or NR 7 , and
  • X 5 , X 6 and X 7 are each
  • X10 is each independently CH or N; X8 and X9 are each independently S or O; 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 at least one of halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 alkyl substituted by at least one halogen, C1-4 alkoxy substituted by at least one halogen, nitro, cyano, -SR6 , -S(O) -R6 , and -S(O) 2 - R6 ; R6 is selected from C1-6 alkyl and C1-6 alkyl substituted by at least one halogen; R7 is selected from H and C1-6 alkyl.
  • R 1 , R 2 , and R 3 are each independently selected from H, halogen, C 1-4 alkyl substituted by at least one halogen, C 1-6 alkoxy substituted by at least one halogen, -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 , and R 3 are not H at the same time;
  • R 4 and R 5 are each independently selected from H, halogen, and C 1-4 alkyl;
  • X 7 is C;
  • A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X 1 , X 2 , and X 3 are each independently CH or N;
  • X 4 is O, S or NR 7 , and
  • X 5 , X 6 and X 7 are each independently CH or N;
  • 10 are each independently CH or N;
  • n R represent
  • R 3 is absent and X 7 is CH.
  • R 1 and R 2 are each independently selected from H, halogen, C 1-4 alkyl substituted by at least one halogen, C 1-6 alkoxy substituted by at least one halogen, -OR 8 ;
  • R 8 is phenyl or phenyl substituted by at least one halogen; and
  • R 1 and R 2 are not H at the same time;
  • R 4 and R 5 are each independently selected from H, halogen, C 1-4 alkyl;
  • R 3 is absent and X 7 is CH;
  • A is a compound of formula (I-1) or The group shown by 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 NR7 , and
  • X5 , X6 and X10 are each independently CH or N;
  • n Rs represent n substituents present at any substitutable position in the A group, and the n substituents
  • R 1 , R 2 , and R 3 are each independently selected from H, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoromethoxy, -OR 8 , or R 3 is absent;
  • R 8 is phenyl substituted by at least one halogen selected from fluorine, chlorine, bromine, and iodine; and
  • R 1 , R 2 , and R 3 are not H at the same time;
  • R 4 and R 5 are each independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl;
  • X 7 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), X 1 , X
  • X6 and X10 are each independently CH or N; X8 and X9 are each independently S or O; 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 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, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, nitro, cyano,
  • R 7 is selected from H and C 1-6 alkyl.
  • R 1 , R 2 , and R 3 are each independently selected from H, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoromethoxy, -OR 8 , or R 3 does not exist;
  • R 8 is phenyl substituted by at least one halogen selected from fluorine, chlorine, bromine, and iodine; and R 1 , R 2 , and R 3 are not H at the same time;
  • R 4 and R 5 are each independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl;
  • X 7 is C;
  • A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X 1 , X 2 , and X 3 are each independently CH or N;
  • X 4 is O,
  • R 3 is absent and X 7 is CH.
  • R 1 and R 2 are each independently selected from H, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoromethoxy, -OR 8 , or R 3 does not exist;
  • R 8 is phenyl substituted by at least one halogen selected from fluorine, chlorine, bromine, and iodine; and R 1 and R 2 are not H at the same time;
  • R 4 and R 5 are each independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl;
  • R 3 does not exist and
  • X 7 is CH;
  • A is a group represented by formula (I-1) or formula (I-2); in formula (I-1) and formula (I-2), X 1 , X 2 , and X 3 are each independently CH or N;
  • X 4 is O, S or NR 7
  • R 1 and R 2 are each independently selected from fluorine, chlorine, bromine, iodine, and trifluoromethyl;
  • R 4 and R 5 are each independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl;
  • R 3 is absent and X 7 is CH;
  • A is a group represented by formula (I-1); in formula (I-1), X 1 , X 2 , X 3 are each independently CH or N;
  • n R 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 at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl,
  • n is 1 or 2.
  • the compound represented by formula (I) is selected from any one of the following:
  • R 1 and R 2 are each independently selected from fluorine, chlorine, bromine, iodine, and trifluoromethyl;
  • R 4 and R 5 are each independently selected from H, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl;
  • R 3 is absent and X 7 is CH;
  • A is a group represented by formula (I-2); in formula (I-2), X 4 is O, S or NR 7 , and X 5 , X 6 and X 10 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 at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-prop
  • n is 0, 1, 2 or 3.
  • the compound represented by formula (I) is selected from any one of the following:
  • 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.
  • 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.
  • the present invention provides the following method for preparing the compound described in the first aspect, the method comprising:
  • intermediate III-A The intermediate II-A is dissolved in chloroform, N-bromosuccinimide and p-toluenesulfonic acid are added, heated to reflux, and the reaction is monitored by TLC. After the reaction is completed, the heating is stopped, water is added to quench the reaction, and then extraction, washing, drying, filtration and desolventization are obtained to obtain intermediate III-A.
  • 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 solids from the system, and a filter cake was obtained by suction filtration. The filter cake was recrystallized with petroleum ether and ethyl acetate to obtain intermediate IV-A.
  • intermediate VA 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 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 VA (wherein R4 and R5 are each independently selected from H, a C1-6 alkyl group).
  • the present invention also provides the following method for preparing the compound described in the first aspect, the method comprising:
  • 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 from the system, and a filter cake was obtained by suction filtration. The filter cake was recrystallized with petroleum ether and ethyl acetate to obtain intermediate IV-B.
  • 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.
  • the second aspect of the present invention provides the use of the compound containing the syneene fragment described in the first aspect in the control of nematodes and/or antifungal.
  • the nematode is a plant parasitic nematode.
  • 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, eggplant root-knot nematodes and other root-knot nematode species; soybean cyst nematodes, beet cyst nematodes, and other Heterodera species.
  • the fungus is selected from at least one of wheat fusarium head blight, cucumber gray mold, rape sclerotinia, wheat stem base rot, wheat powdery mildew
  • the third aspect of the present invention provides a pesticide for controlling nematodes and/or antifungal
  • the pesticide contains an effective amount of active ingredients for controlling nematodes and/or antifungal
  • the active ingredient includes at least one of the compounds containing synephene fragments described in the first aspect.
  • the pesticide contains 0.1-99.99wt% of the active ingredient.
  • 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%.
  • the formulation of the pesticide is selected from at least one of emulsifiable concentrate, suspension, wettable powder, powder, granule, aqueous solution, mother liquor and mother powder.
  • 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.
  • the crops are selected from at least one of melons, solanaceous fruits, beans, cereals, and vegetable crops.
  • 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.
  • the present invention will be described in detail below by way of examples.
  • the raw materials used are all common commercially available products.
  • the room temperature or normal temperature referred to in the present invention refers to 25 ⁇ 2°C.
  • the mixture was extracted with ethyl acetate, and then washed with water and saturated brine for 3 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.
  • Compounds 1 to 19, compounds 24 to 84, compounds 89 to 149, compounds 154 to 214, compounds 219 to 274, compounds 279 to 314, compounds 319 to 345, and compounds 446 to 454 of the present invention are all prepared according to It is prepared by a process similar to compound 1, except that the 2,4-dichloroacetophenone and methyltriphenylphosphonium bromide in step (1) and the 2-(trifluoromethyl)nicotinic acid in step (5) are replaced by the corresponding ketone, phosphorus ylide reagent and carboxylic acid according to the structure of the target compound.
  • Compounds 426 to 445 of the present invention are all 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) are replaced by corresponding ketones and carboxylic acids according to the structures of the target compounds.
  • 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.
  • Test Example 1 Control Effect on Southern Root-Knot Nematodes
  • test compound was dissolved in dimethyl sulfoxide to prepare a 10g/L stock solution, and diluted according to the required concentration of the test. All agents were prepared and used.
  • Selected southern second-instar larvae (J2) with good growth status for experimental testing. Prepare a 96-well cell culture plate, add 90 ⁇ L of the test agent at a concentration of 50mg/L, and then add 10 ⁇ L of the second-instar larvae of southern root-knot nematodes (about 50 J2), and repeat three times. Investigate the mortality of J2 under a microscope 72h after the agent treatment. Calculate the mortality rate and corrected mortality rate. The control effect is shown in Table 2.
  • 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%.
  • Test Example 2 Control effect on wheat stem rot pathogen
  • 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 base rot pathogen.
  • 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 25 ⁇ g/mL and 6.25 ⁇ g/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. The control effect is shown in Table 3.
  • 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%.
  • Test Example 3 Control Effect on Wheat Fusarium Pathogen
  • 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 25 ⁇ g/mL and 6.25 ⁇ g/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. The control effect is shown in Table 4.
  • 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%.
  • 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 cucumber gray mold.
  • 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 25 ⁇ g/mL and 6.25 ⁇ g/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. The control effect is shown in Table 5.
  • 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%.
  • Test Example 5 Control effect on rapeseed sclerotinia
  • 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 25 ⁇ g/mL and 6.25 ⁇ g/mL of the agent, respectively, with 3 replicates for each treatment. All culture plates were placed in a sterile incubator at 25°C for culture. When the colonies grew to two-thirds of the diameter of the culture dish, the cross method was used to measure the colony diameters of the control and treatment colonies and calculate the mycelium growth inhibition rate. The control effects are shown in Table 6.
  • 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%.
  • the compounds provided by the present invention can have excellent inhibitory activity against plant parasitic nematodes at low doses.
  • 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.

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Abstract

涉及农药新化合物领域，公开了含突烯片段的化合物及其应用、用于防治线虫和/或真菌的农药、防治线虫和/或真菌的方法。该化合物具有式(I)所示的结构。所述的含突烯片段的化合物在低剂量下就能够对包括中的至少一种植物寄生线虫和/或真菌具有优异的生物活性。

Description

含突烯片段的化合物及其应用、用于防治线虫和真菌的农药、防治线虫和真菌的方法
相关申请的交叉引用
本申请要求2023年07月31日提交的中国专利申请202310949090.8的权益，该申请的内容通过引用被合并于本文。
技术领域
本发明涉及农药新化合物领域，具体涉及含突烯片段的化合物及其应用、用于防治线虫和真菌的农药、防治线虫和真菌的方法。
背景技术
在农业及园艺等作物生产领域中，线虫会对植物根系产生严重危害，进而导致农业产品及经济作物的重大损失。
因此，需要开发具有活性较高、用量较低且对环境友好的杀线虫剂来防治线虫的危害。
目前有文献已经报道含有羧酰胺衍生物用作于防治线虫病害，如WO2007/108483A1、WO2014/177582A1、WO2013/076230A1、WO2015/007626A1等均涉及芳基甲酰胺和杂芳基甲酰胺，显示出良好的杀有害生物，特别是杀线虫的活性。
但是，目前用于防治线虫药剂仍然较少，且传统杀线虫药剂大多对人体和环境高毒，亟需开发新型高效的杀线虫剂用于线虫病害的防效。
此外，植物性病原真菌也是危害农业及园艺等作物的重大因素，病原真菌和线虫等有害生物的感染会导致农作物品质下降，产量大幅下降，给生产者带来巨大经济损失。目前能用于同时防治植物病原真菌和线虫的药剂较少，因此，需要开发新的药剂来解决这一问题。
发明内容
本发明的目的之一是提供一种能够防治植物寄生线虫的新化合物。
本发明的目的之二是提供一种能够抗真菌的新化合物。
本发明的目的之三是提供一种通过同时防治植物寄生线虫和抗真菌的新化合物。
为了实现上述目的，本发明的第一方面提供一种含突烯片段的化合物，该化合物具有式(I)所示的结构：
其中，在式(I)中，
R1、R2、R3各自独立地选自H、卤素、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基、-O-R8，或者R3不存在；R8为苯基或由至少一个卤素取代的苯基；且R1、R2、R3不同时为H；
R4和R5各自独立地选自H、卤素、C1-6的烷基；
X7为CH或N；
A为式(I-1)、式(I-2)或式(I-3)所示的基团；在式(I-1)、式(I-2)和式(I-3)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；X8和X9各自独立地为S或O；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自卤素、C1-6的烷基、C1-6的烷氧基、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基、硝基、氰基、-S-R6、-S(O)-R6、-S(O)2-R6中的至少一种；
R6选自C1-6的烷基、由至少一个卤素取代的C1-6的烷基；
R7选自H、C1-6的烷基。
本发明的第二方面提供第一方面中所述的含突烯片段的化合物在防治线虫和/或抗真菌中的应用。
本发明的第三方面提供一种用于防治线虫和/或抗真菌的农药，该农药中含有防治线虫和/或抗真菌有效量的活性成分，所述活性成分包括第一方面中所述的含突烯片段的化合物中的至少一种。
本发明的第四方面提供一种防治线虫和/或抗真菌的方法，该方法包括：将用于防治线虫和/或抗真菌的农药施加于农作物上，所述用于防治线虫和/或抗真菌的农药为本发明第三方面中所述的用于防治线虫和/或抗真菌的农药。
本发明提供的含突烯片段的至少部分化合物在低剂量(50mg/L以下，6.25mg/L以下，甚至更低浓度下)下就能够对植物寄生线虫具有优异的抑制活性。
例如，本发明的至少部分化合物在50mg/L浓度下，对二龄南方根结线虫处理48h后，二龄南方根结线虫死亡率>80％；复筛后发现，本发明的化合物在6.25mg/L甚至更低浓度下对二龄南方根结线虫仍然能表现出>80％防效，具有优异的杀线虫活性。
又如，本发明提供的含突烯片段的至少部分化合物在低剂量(25mg/L，6.25mg/L以下，甚至更低浓度下)就能够对小麦茎基腐、小麦赤霉、黄瓜灰霉、油菜菌核等病害具有优异的抑制活性。
又如，本发明的至少部分化合物在25mg/L浓度下，对小麦茎基腐病菌、小麦赤霉病菌、黄瓜灰霉病菌、油菜菌核病菌展现出>80％的防效；复筛后发现，本发明的化合物在6.25mg/L甚至更低浓度下对小麦茎基腐病菌、小麦赤霉病菌、黄瓜灰霉病菌、油菜菌核病菌仍然能展现出>80％的防效，具有优异的杀菌活性。
具体实施方式
在本文中所披露的范围的端点和任何值都不限于该精确的范围或值，这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说，各个范围的端点值之间、各个范围的端点值和单独的点值之间，以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围，这些数值范围应被视为在本文中具体公开。
以下先针对本发明中的部分术语进行解释。
结构式中的虚线表示，式(I)能够与式(I-1)的六元环上的任意位置连接，或者式(I)能够与式(I-2)的五元环上的任意位置连接。
本发明所述卤素包括氟、氯、溴、碘。
本发明所述“由至少一个卤素取代的苯基”表示苯基上的至少一个H原子被卤素取代。
本发明所述“C1-6的烷基”表示碳原子总数为1-6(例如1、2、3、4、5、6)的烷基，包括直链烷基、支链烷基，例如可以为甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基等。针对“C1-4的烷基”具有与此类似的定义，仅仅是碳原子总数不同。
本发明所述“由至少一个卤素取代的C1-6的烷基”表示C1-6的烷基上的至少一个H原子被卤素取代，C1-6的烷基与前述定义相同。针对“由至少一个卤素取代的C1-4的烷基”具有与此类似的定义，仅仅是碳原子总数不同。
“由至少一个卤素取代的C1-6的烷氧基”表示C1-6的烷氧基上的至少一个H原子被卤素取代。C1-6的烷氧基表示碳原子总数为1-6的直链或支链烷氧基，例如碳原子数可以为1、2、3、4、5、6，包括但不限于甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、正戊氧基、异戊氧基、正己氧基等。针对“由至少一个卤素取代的C1-4的烷氧基”具有与此类似的定义，仅仅是碳原子总数不同。
如前所述，本发明的第一方面提供了一种含突烯片段的化合物，该化合物具有式(I)所示的结构。
根据一种优选的具体实施方式(以下称为优选的具体实施方式1)，该化合物具有式(I)所示的结构：其中，在式(I)中，R1、R2、R3各自独立地选自H、卤素、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基、-O-R8，或者R3不存在；R8为苯基或由至少一个卤素取代的苯基；且R1、R2、R3不同时为H；R4和R5各自独立地选自H、卤素、C1-6的烷基；X7为C；A为式(I-1)或式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自卤素、C1-6的烷基、C1-6的烷氧基、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基、硝基、氰基、-S-R6、-S(O)-R6、-S(O)2-R6中的至少一种；R6选自C1-6的烷基、由至少一个卤素取代的C1-6的烷基；R7选自H、C1-6的烷基。
在优选的具体实施方式1中，更优选地，R3不存在且X7为CH。
在优选的具体实施方式1中，进一步优选地，在式(I)中，R1、R2各自独立地选自H、卤素、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基、-O-R8；R8为苯基或由至少一个卤素取代的苯基；且R1、R2不同时为H；R4和R5各自独立地选自H、卤素、C1-6的烷基；R3不存在且X7为CH；A为式(I-1)或式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自卤素、C1-6的烷基、C1-6的烷氧基、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基、硝基、氰基、-S-R6、-S(O)-R6、-S(O)2-R6中的至少一种；R6选自C1-6的烷基、由至少一个卤素取代的C1-6的烷基；R7选自H、C1-6的烷基。
根据一种优选的具体实施方式(以下称为优选的具体实施方式2)，在式(I)中，R1、R2、R3各自独立地选自H、卤素、由至少一个卤素取代的C1-4的烷基、由至少一个卤素取代的C1-6的烷氧基、-O-R8，或者R3不存在；R8为苯基或由至少一个卤素取代的苯基；且R1、R2、R3不同时为H；R4和R5各自独立地选自H、卤素、C1-4的烷基；X7为CH或N；A为式(I-1)、式(I-2)或式(I-3)所示的基团；在式(I-1)、式(I-2)和式(I-3)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；X8和X9各自独立地为S或O；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自卤素、C1-4的烷基、C1-4的烷氧基、由至少一个卤素取代的C1-4的烷基、由至少一个卤素取代的C1-4的烷氧基、硝基、氰基、-S-R6、-S(O)-R6、-S(O)2-R6中的至少一种；R6选自C1-6的烷基、由至少一个卤素取代的C1-6的烷基；R7选自H、C1-6的烷基。
在优选的具体实施方式2中，更优选地，在式(I)中，R1、R2、R3各自独立地选自H、卤素、由至少一个卤素取代的C1-4的烷基、由至少一个卤素取代的C1-6的烷氧基、-O-R8，或者R3不存在；R8为苯基或由至少一个卤素取代的苯基；且R1、R2、R3不同时为H；R4和R5各自独立地选自H、卤素、C1-4的烷基；X7为C；A为式(I-1)或式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自卤素、C1-4的烷基、C1-4的烷氧基、由至少一个卤素取代的C1-4的烷基、由至少一个卤素取代的C1-4的烷氧基、硝基、氰基、-S-R6、-S(O)-R6、-S(O)2-R6中的至少一种；R6选自C1-6的烷基、由至少一个卤素取代的C1-6的烷基；R7选自H、C1-6的烷基。
在优选的具体实施方式2中，进一步优选地，R3不存在且X7为CH。
在优选的具体实施方式2中，特别优选地，在式(I)中，R1、R2各自独立地选自H、卤素、由至少一个卤素取代的C1-4的烷基、由至少一个卤素取代的C1-6的烷氧基、-O-R8；R8为苯基或由至少一个卤素取代的苯基；且R1、R2不同时为H；R4和R5各自独立地选自H、卤素、C1-4的烷基；R3不存在且X7为CH；A为式(I-1)或 式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自卤素、C1-4的烷基、C1-4的烷氧基、由至少一个卤素取代的C1-4的烷基、由至少一个卤素取代的C1-4的烷氧基、硝基、氰基、-S-R6、-S(O)-R6、-S(O)2-R6中的至少一种；R6选自C1-6的烷基、由至少一个卤素取代的C1-6的烷基；R7选自H、C1-6的烷基。
根据一种优选的具体实施方式(以下称为优选的具体实施方式3)，在式(I)中，R1、R2、R3各自独立地选自H、氟、氯、溴、碘、三氟甲基、三氟甲氧基、-O-R8，或者R3不存在；R8为由至少一个选自氟、氯、溴、碘的卤素取代的苯基；且R1、R2、R3不同时为H；R4和R5各自独立地选自H、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基；X7为CH或N；A为式(I-1)、式(I-2)或式(I-3)所示的基团；在式(I-1)、式(I-2)和式(I-3)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；X8和X9各自独立地为S或O；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、叔丁硫基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、硝基、氰基、-S(O)-R6、-S(O)2-R6中的至少一种；R6选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基；X7为CH或N。
在优选的具体实施方式3中，更优选地，R7选自H、C1-6的烷基。
在优选的具体实施方式3中，更加优选地，在式(I)中，R1、R2、R3各自独立地选自H、氟、氯、溴、碘、三氟甲基、三氟甲氧基、-O-R8，或者R3不存在；R8为由至少一个选自氟、氯、溴、碘的卤素取代的苯基；且R1、R2、R3不同时为H；R4和R5各自独立地选自H、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基；X7为C；A为式(I-1)或式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、叔丁硫基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、硝基、氰基、-S(O)-R6、-S(O)2-R6中的至少一种；R6选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基；R7选自H、C1-6的烷基。
在优选的具体实施方式3中，进一步优选地，R3不存在且X7为CH。
在优选的具体实施方式3中，更进一步优选地，在式(I)中，R1、R2各自独立地选自H、氟、氯、溴、碘、三氟甲基、三氟甲氧基、-O-R8，或者R3不存在；R8为由至少一个选自氟、氯、溴、碘的卤素取代的苯基；且R1、R2不同时为H；R4和R5各自独立地选自H、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基；R3不存在且X7为CH；A为式(I-1)或式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、叔丁硫基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、硝基、氰基、-S(O)-R6、-S(O)2-R6中的至少一种；R6选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、二氟甲基、三氟甲基、二氟甲氧基、 三氟甲氧基；R7选自H、C1-6的烷基。
根据一种优选的具体实施方式(以下称为优选的具体实施方式4)，在式(I)中，R1、R2各自独立地选自氟、氯、溴、碘、三氟甲基；R4和R5各自独立地选自H、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基；R3不存在且X7为CH；A为式(I-1)所示的基团；在式(I-1)中，X1、X2、X3各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、叔丁硫基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、-S(O)2-R6中的至少一种；R6选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基。
在优选的具体实施方式4中，更优选地，n为1或2。
在本发明中，进一步优选地，式(I)所示的化合物选自以下中的任意一种：


根据一种优选的具体实施方式(以下称为优选的具体实施方式5)，在式(I)中，R1、R2各自独立地选自氟、氯、溴、碘、三氟甲基；R4和R5各自独立地选自H、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基；R3不存在且X7为CH；A为式(I-2)所示的基团；在式(I-2)中，X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、二氟甲基、三氟甲基中的至少一种；R7为H或甲基。
在优选的具体实施方式5中，更优选地，n为0、1、2或3。
在本发明中，进一步优选地，式(I)所示的化合物选自以下中的任意一种：



在本发明中，进一步优选地，式(I)所示的化合物选自化合物1至化合物19、化合物24至化合物84、化合物89至化合物149、化合物154至化合物214、化合物219至化合物274、化合物279至化合物314、化合物319至化合物345、化合物426至化合物454中的任意一种。
本发明对制备第一方面中所述的化合物的具体方法没有特别的要求，本领域技术人员可以根据本发明公开的结构式，结合农药有机合成领域内的已知知识确定合适的制备路线获得第一方面所述的化合物。
示例性地，本发明提供以下方法制备第一方面中所述的化合物，该方法包括：
中间体II-A的合成：将超干THF(四氢呋喃)加入烷基三苯基溴化膦中，冰水浴下加入叔丁醇钾，0-25℃下反应5-60min后，在冰水浴下加入各种取代的酮，待加完后升温至室温，1-5h后TLC监测反应完全，加水猝灭，然后萃取、洗涤、干燥、过滤脱溶、分离纯化，得到中间体II-A。
中间体III-A的合成：将所述中间体II-A溶于三氯甲烷中，加入N-溴代丁二酰亚胺和对甲苯磺酸，加热回流，TLC监测反应，待反应完成后，停止加热，加水猝灭反应，然后萃取、洗涤、干燥、过滤脱溶，得到中间体III-A。
中间体IV-A的合成：将所述中间体III-A溶于N,N-二甲基甲酰胺中，0-40℃下加入邻苯二甲酰亚胺钾，0-40℃反应5h，TLC监测反应完全后，往体系中加入冰水使体系析出固体，抽滤得到滤饼，滤饼用石油醚和乙酸乙酯进行重结晶，得到中间体IV-A。
中间体V-A的合成：将所述中间体IV-A溶于乙醇中，加入水合肼，加热回流3-5h，体系析出白色固体，TLC监测反应完成后，停止加热，将体系冷却至-10℃至0℃，抽滤得到滤液，然后萃取、洗涤、干燥、脱溶，得到中间体V-A(其中，R4和R5各自独立地选自H、C1-6的烷基)。
式(I)化合物的合成：将所述中间体V-A溶于乙腈中，在冰浴下加入不同的羧酸，N-甲基咪唑和N,N,N',N'-四甲基氯甲脒六氟磷酸盐，TLC监测反应完成后，然后萃取、洗涤、分离纯化，得到目标化合物，也即式(I)化合物。
示例性地，本发明还提供以下方法制备第一方面中所述的化合物，该方法包括：
中间体II-B的合成：将二氯甲烷加入各种取代的苯乙酮中，冰水浴下加入三苯基膦和三氯溴甲烷，TLC监测反应完全，加水猝灭，然后萃取、洗涤、干燥、过滤脱溶、分离纯化，得到中间体II-B。
中间体III-B的合成：将所述中间体II-B溶于三氯甲烷中，加入N-溴代丁二酰亚胺和对甲苯磺酸，加热回流， TLC监测反应，待反应完成后，停止加热，加水猝灭反应，然后萃取、洗涤、干燥、过滤脱溶，得到中间体III-B。
中间体IV-B的合成：将所述中间体III-B溶于N,N-二甲基甲酰胺中，0-40℃下加入邻苯二甲酰亚胺钾，0-40℃反应5h，TLC监测反应完全后，往体系中加入冰水使体系析出固体，抽滤得到滤饼，滤饼用石油醚和乙酸乙酯进行重结晶，得到中间体IV-B。
中间体V-B的合成：将所述中间体IV-B溶于乙醇中，加入水合肼，加热回流3-5h，体系析出白色固体，TLC监测反应完成后，停止加热，将体系冷却至-10℃至0℃，抽滤得到滤液，然后萃取、洗涤、干燥、脱溶，得到中间体V-B。
式(I)化合物的合成：将所述中间体V-B溶于乙腈中，在冰浴下加入不同的羧酸，N-甲基咪唑和N,N,N',N'-四甲基氯甲脒六氟磷酸盐，TLC监测反应完成后，然后萃取、洗涤、分离纯化，得到目标化合物，也即式(I)化合物。
在没有特别说明的情况下，本发明对前述制备方法中涉及的条件和具体操作参数没有特别的限定，本领域技术人员可以根据本领域内已知的知识进行选择，也可以根据本发明的后文中列举的实例中提供的参数和条件进行选择，本发明在此不再赘述，本领域技术人员不应理解为对本发明的限制。
如前所述，本发明的第二方面提供了第一方面中所述的含突烯片段的化合物在防治线虫和/或抗真菌中的应用。优选地，所述线虫为植物寄生线虫。更优选情况下，所述线虫选自南方根结线虫、花生根结线虫、爪哇根结线虫、北方根结线虫、水稻根结线虫、黄瓜根结线虫、番茄根结线虫、香蕉根结线虫、烟草根结线虫、西瓜根结线虫、南瓜根结线虫、甜瓜根结线虫、茄子根结线虫及其他根结线虫属种类；大豆胞囊线虫、甜菜胞囊线虫、以及其他异皮线虫属种类中的至少一种。进一步优选地，所述真菌选自小麦赤霉病菌、黄瓜灰霉病菌、油菜菌核病菌、小麦茎基腐病菌、小麦白粉病菌、黄瓜白粉病菌中的至少一种。
如前所述，本发明的第三方面提供了一种用于防治线虫和/或抗真菌的农药，该农药中含有防治线虫和/或抗真菌有效量的活性成分，所述活性成分包括第一方面中所述的含突烯片段的化合物中的至少一种。优选地，所述农药中含有0.1-99.99wt％的所述活性成分。示例性地，在所述农药中，所述化合物的含量为1wt％、5wt％、10wt％、15wt％、20wt％、25wt％、30wt％、35wt％、40wt％、45wt％、50wt％、55wt％、60wt％、65wt％、70wt％、75wt％、80wt％、85wt％、90wt％、95wt％。优选情况下，该农药的剂型选自乳油、悬浮剂、可湿性粉剂、粉剂、粒剂、水剂、母液和母粉中的至少一种。
如前所述，本发明的第四方面提供了一种防治线虫和/或抗真菌的方法，该方法包括：将用于防治线虫和/或抗真菌的农药施加于农作物上，所述用于防治线虫和/或抗真菌的农药为本发明第三方面中所述的用于防治线虫的农药。优选地，所述农作物选自瓜类、茄果类、豆类、禾谷、蔬菜类农作物中的至少一种。更优选地，所述农作物选自小麦、黄瓜、油菜、花生、水稻、马铃薯、萝卜、葫萝卜、莴苣、白菜、葡萄、柑橘、甘蔗、香蕉、火龙果、辣椒、芹菜、柑橘、西瓜、番茄中的至少一种。
以下将通过实例对本发明进行详细描述。以下实例中在没有特别说明的情况下，使用的原料均为普通的市售品。在没有特别说明的情况下，本发明涉及的室温或者常温均表示25±2℃。
实施例1：化合物1的制备
(1)取甲基三苯基溴化膦(75mmol,1.5eq.)于250ml茄形瓶中，加入100ml超干THF，冰水浴下加入叔 丁醇钾(75mmol,1.5eq.)，室温反应20min后，在冰水浴下加入2,4-二氯苯乙酮(50mmol,1eq.)，待加完后升温至室温，2h后TLC监测反应完全，加水猝灭，用乙酸乙酯萃取，再分别用水、饱和食盐水洗涤3次，用无水硫酸钠干燥后过滤脱溶，得到粗品。粗品经硅胶柱层析分离纯化，得到呈无色油状液体的中间体1。
(2)将中间体1(40mmol，1eq.)溶于三氯甲烷中，加入N-溴代丁二酰亚胺(NBS，44mmol，1.1eq.)和对甲苯磺酸(TsOH，12mmol，0.3eq.)，65℃下加热回流，TLC监测反应，待反应完成后，停止加热，加水猝灭反应，反应冷却至室温后用二氯甲烷和水萃取，再用饱和食盐水洗3次，经无水硫酸钠干燥后脱溶，得到黄色油状液体中间体2。
(3)将中间体2(35mmol，1eq.)溶于N,N-二甲基甲酰胺(DMF)中，室温下加入邻苯二甲酰亚胺钾(52.5mmol，1.5eq.)，室温反应5h，TLC监测反应完全后，往体系中加入大量冰水使体系析出固体，抽滤得到滤饼，滤饼用石油醚和乙酸乙酯进行重结晶，得到白色固体中间体3。
(4)将上述中间体3(20mmol，1eq.)溶于乙醇中，加入水合肼(质量分数为85％)(40mmol，2eq.)，加热回流4h，体系析出白色固体，TLC监测反应完成后，停止加热，将体系冷却至0℃，抽滤得到滤液，用乙酸乙酯萃取，再分别用水、饱和食盐水洗涤3次，无水硫酸钠干燥，脱溶得到黄色油状液体中间体4。
(5)将中间体4(2mmol，1eq.)溶于乙腈中，在冰浴下加入2-(三氟甲基)烟酸(2.4mmol，1.2eq.)，N-甲基咪唑(NMI，7mmol，3.5eq.)和N,N,N',N'-四甲基氯甲脒六氟磷酸盐(TCFH，2.4mmol，1.2eq.)，TLC监测反应完成后，用乙酸乙酯萃取，再分别用水、饱和食盐水洗涤3次，硅胶拌样后柱层析分离，得到白色固体化合物1。
实施例2：化合物426的制备
(1)取2,4-二氯苯乙酮(50mmol,1eq.)于250ml茄形瓶中，加入100ml二氯甲烷，冰水浴下加入三苯基膦(225mmol,4.5eq.)和三氯溴甲烷(150mmol,3eq.)，TLC监测反应完全，加水猝灭，用二氯甲烷萃取，再分别用水、饱和食盐水洗涤3次，用无水硫酸钠干燥后过滤脱溶，得到粗品。粗品经硅胶柱层析分离纯化，得到呈无色油状液体的中间体1。
(2)将中间体1(40mmol，1eq.)溶于三氯甲烷中，加入N-溴代丁二酰亚胺(NBS，44mmol，1.1eq.)和对甲苯磺酸(TsOH，12mmol，0.3eq.)，65℃下加热回流，TLC监测反应，待反应完成后，停止加热，加水猝灭反应，反应冷却至室温后用二氯甲烷和水萃取，再用饱和食盐水洗3次，经无水硫酸钠干燥后脱溶，得到黄色油状液体中间体2。
(3)将中间体2(35mmol，1eq.)溶于N,N-二甲基甲酰胺(DMF)中，室温下加入邻苯二甲酰亚胺钾(52.5mmol，1.5eq.)，室温反应5h，TLC监测反应完全后，往体系中加入大量冰水使体系析出固体，抽滤得到滤饼，滤饼用石油醚和乙酸乙酯进行重结晶，得到白色固体中间体3。
(4)将上述中间体3(20mmol，1eq.)溶于乙醇中，加入水合肼(质量分数为85％)(40mmol，2eq.)，加热回流4h，体系析出白色固体，TLC监测反应完成后，停止加热，将体系冷却至0℃，抽滤得到滤液，用乙酸乙酯萃取，再分别用水、饱和食盐水洗涤3次，无水硫酸钠干燥，脱溶得到黄色油状液体中间体4。
(5)将中间体4(2mmol，1eq.)溶于乙腈中，在冰浴下加入2-(三氟甲基)烟酸(2.4mmol，1.2eq.)，N-甲基咪唑(NMI，7mmol，3.5eq.)和N,N,N',N'-四甲基氯甲脒六氟磷酸盐(TCFH，2.4mmol，1.2eq.)，TLC监测反应完成后，用乙酸乙酯萃取，再分别用水、饱和食盐水洗涤3次，硅胶拌样后柱层析分离，得到白色固体化合物426。
本发明的化合物1至化合物19、化合物24至化合物84、化合物89至化合物149、化合物154至化合物214、化合物219至化合物274、化合物279至化合物314、化合物319至化合物345、化合物446至化合物454均按 照与化合物1相似的流程制备得到，所不同的是，将步骤(1)中的2,4-二氯苯乙酮、甲基三苯基溴化膦和步骤(5)中的2-(三氟甲基)烟酸根据目标化合物的结构替换为对应的酮、磷叶立德试剂和羧酸。
本发明的化合物426至化合物445均按照与化合物426相似的流程制备得到，所不同的是，将步骤(1)中的2,4-二氯苯乙酮和步骤(5)中的2-(三氟甲基)烟酸根据目标化合物的结构替换为对应的酮和羧酸。
本发明部分具体化合物的表征数据如表1所示。
表1



对比例1
根据CN113845480A中公开的方法制备化合物CN-1。通过实验研究发现，该化合物在50mg/L浓度下，对二龄南方根结线虫处理48h后，二龄南方根结线虫死亡率<20％，几乎没有展现出对线虫的防效。
测试例1：对南方根结线虫的防治效果
将待测化合物使用二甲基亚砜溶解配制成10g/L的母液，按试验所需浓度进行稀释，所有药剂均现配使用。选择生长状态良好的南方二龄幼虫(J2)进行试验测试。准备96孔细胞培养板，加入50mg/L浓度供试药剂90μL，再加入南方根结线虫二龄幼虫10μL(约50条J2)，重复三次。于药剂处理后72h在显微镜下调查J2死亡率。计算死亡率和校正死亡率。防治效果如表2中所示。
表2

A、B、C、D、E表示防效等级，且80％≦A≦100％；70％≦B<80％；60％≦C<70％,50％≦D<60％；E<50％。
测试例2：对小麦茎基腐病菌的防治效果
将待测化合物用二甲基亚砜溶解并稀释，制成母液。采用菌丝生长速率法测定药剂对小麦茎基腐病菌的菌丝生长抑制效果。在连续转接培养4d的菌落边缘打取直径为5mm的菌碟，分别将菌碟接种于含药剂浓度为25μg/mL，6.25μg/mL的PDA平板上，每个处理3个重复。将所有的培养皿置25℃的无菌培养箱进行培养。待空白对照菌长到培养皿直径的三分之二时，采用十字交叉法测定对照及处理的菌落直径并计算菌丝生长抑制率。防治效果如表3中所示。
表3
A、B、C、D、E表示防效等级，且80％≦A≦100％；70％≦B<80％；60％≦C<70％,50％≦D<60％；E<50％。
测试例3：对小麦赤霉病菌的防治效果
将待测化合物用二甲基亚砜溶解并稀释，制成母液。采用菌丝生长速率法测定药剂对小麦赤霉病菌的菌丝生长抑制效果。在连续转接培养4d的菌落边缘打取直径为5mm的菌碟，分别将菌碟接种于含药剂浓度为25μg/mL，6.25μg/mL的PDA平板上，每个处理3个重复。将所有的培养皿置25℃的无菌培养箱进行培养。待空白对照菌长到培养皿直径的三分之二时，采用十字交叉法测定对照及处理的菌落直径并计算菌丝生长抑制率。防治效果如表4中所示。
表4

A、B、C、D、E表示防效等级，且80％≦A≦100％；70％≦B<80％；60％≦C<70％,50％≦D<60％；E<50％。
测试例4：对黄瓜灰霉病菌的防治效果
将待测化合物用二甲基亚砜溶解并稀释，制成母液。采用菌丝生长速率法测定药剂对黄瓜灰霉病菌的菌丝生长抑制效果。在连续转接培养4d的菌落边缘打取直径为5mm的菌碟，分别将菌碟接种于含药剂浓度为25μg/mL，6.25μg/mL的PDA平板上，每个处理3个重复。将所有的培养皿置25℃的无菌培养箱进行培养。待空白对照菌长到培养皿直径的三分之二时，采用十字交叉法测定对照及处理的菌落直径并计算菌丝生长抑制率。防治效果如表5中所示。
表5
A、B、C、D、E表示防效等级，且80％≦A≦100％；70％≦B<80％；60％≦C<70％,50％≦D<60％；E<50％。
测试例5：对油菜菌核病菌的防治效果
将待测化合物用二甲基亚砜溶解并稀释，制成母液。采用菌丝生长速率法测定药剂对油菜菌核病菌的菌丝生长抑制效果。在连续转接培养4d的菌落边缘打取直径为5mm的菌碟，分别将菌碟接种于含药剂浓度为25μg/mL，6.25μg/mL的PDA平板上，每个处理3个重复。将所有的培养皿置25℃的无菌培养箱进行培养。待空白对照菌 长到培养皿直径的三分之二时，采用十字交叉法测定对照及处理的菌落直径并计算菌丝生长抑制率。防治效果如表6中所示。
表6
A、B、C、D、E表示防效等级，且80％≦A≦100％；70％≦B<80％；60％≦C<70％,50％≦D<60％；E<50％。
由上述结果可知，本发明提供的化合物在低剂量下就能够对植物寄生线虫具有优异的抑制活性，同时，本发明的化合物还对小麦赤霉、小麦茎基腐、黄瓜灰霉、油菜菌核等病菌具有优异的抑制活性。
以上详细描述了本发明的优选实施方式，但是，本发明并不限于此。在本发明的技术构思范围内，可以对本发明的技术方案进行多种简单变型，包括各个技术特征以任何其它的合适方式进行组合，这些简单变型和组合同样应当视为本发明所公开的内容，均属于本发明的保护范围。

Claims (12)

  1. 一种含突烯片段的化合物，其特征在于，该化合物具有式(I)所示的结构：
    其中，在式(I)中，
    R1、R2、R3各自独立地选自H、卤素、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基、-O-R8，或者R3不存在；R8为苯基或由至少一个卤素取代的苯基；且R1、R2、R3不同时为H；
    R4和R5各自独立地选自H、卤素、C1-6的烷基；
    X7为C；
    A为式(I-1)或式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自卤素、C1-6的烷基、C1-6的烷氧基、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基、硝基、氰基、-S-R6、-S(O)-R6、-S(O)2-R6中的至少一种；
    R6选自C1-6的烷基、由至少一个卤素取代的C1-6的烷基；
    R7选自H、C1-6的烷基；
    优选地，R3不存在且X7为CH。
  2. 根据权利要求1所述的含突烯片段的化合物，其特征在于，在式(I)中，
    R1、R2、R3各自独立地选自H、卤素、由至少一个卤素取代的C1-4的烷基、由至少一个卤素取代的C1-6的烷氧基、-O-R8，或者R3不存在；R8为苯基或由至少一个卤素取代的苯基；且R1、R2、R3不同时为H；
    R4和R5各自独立地选自H、卤素、C1-4的烷基；
    X7为C；
    A为式(I-1)或式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N；X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自卤素、C1-4的烷基、C1-4的烷氧基、由至少一个卤素取代的C1-4的烷基、由至少一个卤素取代的C1-4的烷氧基、硝基、氰基、-S-R6、-S(O)-R6、-S(O)2-R6中的至少一种；
    R6选自C1-6的烷基、由至少一个卤素取代的C1-6的烷基；
    R7选自H、C1-6的烷基；
    优选地，R3不存在且X7为CH。
  3. 根据权利要求1所述的含突烯片段的化合物，其特征在于，在式(I)中，
    R1、R2、R3各自独立地选自H、氟、氯、溴、碘、三氟甲基、三氟甲氧基、-O-R8，或者R3不存在；R8为由至少一个选自氟、氯、溴、碘的卤素取代的苯基；且R1、R2、R3不同时为H；
    R4和R5各自独立地选自H、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基；
    X7为C；
    A为式(I-1)或式(I-2)所示的基团；在式(I-1)和式(I-2)中，X1、X2、X3各自独立地为CH或N； X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、叔丁硫基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、硝基、氰基、-S(O)-R6、-S(O)2-R6中的至少一种；
    R6选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基；
    R7选自H、C1-6的烷基；
    优选地，R3不存在且X7为CH。
  4. 根据权利要求3所述的含突烯片段的化合物，其特征在于，在式(I)中，
    R1、R2各自独立地选自氟、氯、溴、碘、三氟甲基；
    R4和R5各自独立地选自H、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基；
    R3不存在且X7为CH；
    A为式(I-1)所示的基团；在式(I-1)中，X1、X2、X3各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、叔丁硫基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、-S(O)2-R6中的至少一种；
    R6选自甲基、乙基、正丙基、异丙基、正丁基、叔丁基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基；
    优选地，n为1或2；
    更优选地，式(I)所示的化合物选自以下中的任意一种：


  5. 根据权利要求3所述的含突烯片段的化合物，其特征在于，在式(I)中，
    R1、R2各自独立地选自氟、氯、溴、碘、三氟甲基；
    R4和R5各自独立地选自H、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基；
    R3不存在且X7为CH；
    A为式(I-2)所示的基团；在式(I-2)中，X4为O、S或NR7，X5、X6和X10各自独立地为CH或N；n个R表示A基团中任意能够被取代的位置上存在的n个取代基，且n个取代基相同或不同，各自独立地选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基、二氟甲基、三氟甲基中的至少一种；
    R7为H或甲基；
    优选地，n为0、1、2或3；
    更优选地，式(I)所示的化合物选自以下中的任意一种：



  6. 根据权利要求1所述的含突烯片段的化合物，其特征在于，式(I)所示的化合物选自以下中的任意一种：





  7. 权利要求1-6中任意一项所述的含突烯片段的化合物在防治线虫和/或抗真菌中的应用。
  8. 根据权利要求7所述的应用，其特征在于，所述线虫为植物寄生线虫；
    优选地，所述线虫选自南方根结线虫、花生根结线虫、爪哇根结线虫、北方根结线虫、水稻根结线虫、黄瓜根结线虫、番茄根结线虫、香蕉根结线虫、烟草根结线虫、西瓜根结线虫、南瓜根结线虫、甜瓜根结线虫、茄 子根结线虫、大豆胞囊线虫、甜菜胞囊线虫中的至少一种。
  9. 一种用于防治线虫和/或抗真菌的农药，其特征在于，该农药中含有防治线虫和/或抗真菌有效量的活性成分，所述活性成分包括权利要求1-6中任意一项所述的含突烯片段的化合物中的至少一种。
  10. 根据权利要求9所述的用于防治线虫和/或抗真菌的农药，其特征在于，所述农药中含有0.1-99.99wt％的所述活性成分。
  11. 根据权利要求9或10所述的用于防治线虫和/或抗真菌的农药，其特征在于，该农药的剂型选自乳油、悬浮剂、可湿性粉剂、粉剂、粒剂、水剂、母液和母粉中的至少一种。
  12. 一种防治线虫和/或抗真菌的方法，其特征在于，该方法包括：将用于防治线虫和/或抗真菌的农药施加于农作物上，所述用于防治线虫和/或抗真菌的农药为权利要求9-11中任意一项所述的用于防治线虫和/或抗真菌的农药；
    优选地，所述农作物选自瓜类、茄果类、豆类、禾谷、蔬菜类农作物中的至少一种；
    优选地，所述农作物选自小麦、黄瓜、油菜、花生、水稻、马铃薯、萝卜、胡萝卜、莴苣、白菜、葡萄、柑橘、甘蔗、香蕉、火龙果、辣椒、芹菜、柑橘、西瓜、番茄中的至少一种。
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