CN109020928A - A kind of nematicide of structure novel and application thereof - Google Patents

A kind of nematicide of structure novel and application thereof Download PDF

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Publication number
CN109020928A
CN109020928A CN201810939874.1A CN201810939874A CN109020928A CN 109020928 A CN109020928 A CN 109020928A CN 201810939874 A CN201810939874 A CN 201810939874A CN 109020928 A CN109020928 A CN 109020928A
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alkyl
nematicide
formula
halogenated
halogen atoms
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Inventor
唐剑峰
潘光民
刘杰
赵恭文
吴建挺
李冬蓉
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SHANDONG UNITED PESTICIDE INDUSTRY Co Ltd
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SHANDONG UNITED PESTICIDE INDUSTRY Co Ltd
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Priority to CN201810939874.1A priority Critical patent/CN109020928A/en
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
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Abstract

The invention discloses nematicides of a kind of structure novel and application thereof, structure in structural formula containing polyfluoro butylene and lactonic ring, thus there is good control efficiency to the ovum of root-knot nematode and second instar larvae, can especially inhibit the hatching of the root-knot nematode eggs such as cucumber, tomato, tobacco, soybean well；And the toxicity of the novel nematicide of structure of the invention is lower, and the residual in crops is few, small to the harmfulness of people, animal, solves existing nematicide very well and is more toxic, and the more problem of the residual in crop improves the safety of agricultural production；Antibody will not be generated to nematicide of the invention using pest in a long time, there is good nematicidal effect.

Description

A kind of nematicide of structure novel and application thereof
Technical field
The present invention relates to the trifluorobutene class nematicide of nematicide technical field more particularly to a kind of structure novel and Its purposes.
Technical background
Nematode lives in the soil mostly or colonizes in plant, by soil or seed dispersal, can destroy plant Root system, or the organ of intrusion aerial part, influence the growth and development of crops, and propagate disease caused by other microorganisms indirectly Evil, causes agriculturally very huge economic loss.
Existing nematicide is to have penetrated toxic action by nematode epidermal.It is compared with insecticide, fungicide, at present generation The relatively good nematicide of dedicated effect is seldom in boundary, and only more than ten, and due to the preferable nematicidal of existing effect Agent is higher to the toxicity of people and animals, some kinds have phytotoxicity to crop, influences its use, so novel, efficient, environment amenable Nematicide is urgently developed.
Summary of the invention
The purpose of the present invention is aiming at the problems existing in the prior art, provide a kind of nematicide of structure novel and its Purposes.
The present invention is in order to achieve the above object, adopted the technical scheme that:
A kind of nematicide of structure novel, structure are shown in formula I:
Wherein, R1For the aliphatic hydrocarbon of C1-C16, five-ring heterocycles, hexa-member heterocycle or condensed ring in addition to phenyl ring；R2For hydrogen atom Or halogen atom.
Preferably, R1For ethyl, propyl,
Preferably, R1For
Preferably, R1Are as follows:
Preferably, R1Are as follows:
Preferably, R2For fluorine atom.
It preferably, include transconfiguration shown in Formula II, specific structural formula in the compound of Formulas I are as follows:
The invention also includes a kind of purposes of the nematicide of structure novel, for preventing and treating the root knot line on agricultural crops Worm.
The present invention has the advantages that
The nematicide of structure novel of the invention is due to the structure containing polyfluoro butylene and lactonic ring, thus to root knot line The ovum and second instar larvae of worm have good control efficiency, can especially inhibit the root knots line such as cucumber, tomato, tobacco, soybean well The hatching of worm's ovum；And the toxicity of the novel nematicide of structure of the invention is lower, and the residual in crops is few, to people, animal Harmfulness it is small, solve existing nematicide very well and be more toxic, the more problem of residual in crop improves agriculture The safety of industry production；Antibody will not be generated to nematicide of the invention using pest in a long time, have good Nematicidal effect.
Specific embodiment
A kind of nematicide of structure novel, structural formula are shown in formula I:
Wherein: R1For aliphatic hydrocarbon, five-ring heterocycles, hexa-member heterocycle or condensed ring in addition to phenyl ring；R2It is former for hydrogen atom or halogen Son.
Preferably, R2 is hydrogen, fluorine, chlorine or bromine atom；
Preferably, R2 is fluorine atom；
Preferably, R1 is the alkyl or cycloalkyl of C1-C64；
Preferably, R1 is the alkyl or cycloalkyl of C1-C16；
Preferably, R1 is five-ring heterocycles, specifically includes:
The heterocycle of R1 expression general formula R 1-1
In formula ,-R3 and R4 are identical or different, can be hydrogen atom, halogen atom, amino, nitro, C1-C4- alkyl or tool There is the C1-C4- halogenated alkyl of 1 to 5 halogen atoms；
- R5 can be halogen atom, nitro, C1-C4- alkyl or the C1-C4- alkyl halide with 1 to 5 halogen atoms Base.
The heterocycle of R1 expression general formula R 1-2
In formula:
- R6 can be hydrogen atom, halogen atom, C1-C4- alkyl or the C1-C4- alkyl halide with 1 to 5 halogen atoms Base；
- R7 and R8 may be the same or different, can be hydrogen atom, halogen atom, amino, C1-C4- alkyl or have 1 to 5 The C1-C4- halogenated alkyl of halogen atom；
The heterocycle of R1 expression general formula R 1-3
In formula:
- R9 can be halogen atom, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms；
- R10 can be hydrogen atom, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-4)
In formula:
- R11 and R12 can be identical or different, can be hydrogen atom, halogen atom, amino, C1-C4- alkyl, has 1 to arrive The C1-C4- halogenated alkyls of 5 halogen atoms, C1-C4- alkylthio group, C1-C4- alkyl sulphonyl, optionally by halogen atom or C1- The alkyl-substituted phenyl of C4-, or optionally by halogen atom or the alkyl-substituted pyridyl group of C1-C4-；
- R13 can be halogen atom, cyano, C1-C4- alkyl, the C1-C4- halogenated alkyl with 1 to 5 halogen atoms Or the C1-C4- halogenated alkoxy with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-5)
In formula:
- R14 and R15 can be identical or different, can be hydrogen atom, halogen atom, C1-C4- alkyl, C1-C4- alcoxyl Base, the C1-C4- halogenated alkyl with 1 to 5 halogen atoms；
It is halogenated that-R16 can be hydrogen atom, halogen atom, C1-C4- alkyl or C1-C4- with 1 to 5 halogen atoms Alkyl.
R1 indicates the heterocycle of general formula (R1-6)
In formula:
- R17 can be hydrogen atom, halogen atom, cyano, C1-C4- alkyl or the C1-C4- with 1 to 5 halogen atoms Halogenated alkyl；
- R18 and R20 may be the same or different, and can be hydrogen atom, halogen atom, C1-C4- alkyl or have 1 to 5 halogen The C1-C4- halogenated alkyl of plain atom；
- R19 can be hydrogen atom, cyano, C1-C4- alkyl, the C1-C4- halogenated alkyl with 1 to 5 halogen atoms, C1-C4- alkoxy -C 1-C4- alkyl, hydroxyl-C1-C4- alkyl, C1-C4- alkyl sulphonyl, two (C1-C4- alkyl) amino sulphurs Acyl group, C1-C6- alkyl-carbonyl, optionally by halogen atom or the alkyl-substituted phenyl sulfonyl of C1-C4-, or optionally by halogen original Son or the alkyl-substituted benzoyl of C1-C4.
R1 indicates the heterocycle of general formula (R1-7)
In formula:
- R21 can be hydrogen atom, cyano, C1-C4- alkyl, the C1-C4- halogenated alkyl with 1 to 5 halogen atoms, C1-C4- alkoxy -C 1-C4- alkyl, hydroxyl-C1-C4- alkyl, C1-C4- alkyl sulphonyl, two (C1-C4- alkyl) amino sulphurs Acyl group, C1-C6- alkyl-carbonyl, optionally by halogen atom or the alkyl-substituted phenyl sulfonyl of C1-C4-, or optionally by halogen original Son or the alkyl-substituted benzoyl of C1-C4-；
- R22, R23 and R24 may be the same or different, and can be hydrogen atom, halogen atom, cyano, C1-C4- alkyl, have 1 To the C1-C4- halogenated alkyl or C1-C4- alkyl-carbonyl of 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-8)
In formula:
- R25 can be hydrogen atom or C1-C4- alkyl；
- R26 can be halogen atom, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-9)
In formula:
- R27 can be hydrogen atom or C1-C4- alkyl；
- R28 can be halogen atom, C1-C4- alkyl, the C1-C4- halogenated alkyl with 1 to 5 halogen atoms or appoint Choosing is by halogen atom or the alkyl-substituted phenyl of C1-C4-.
R1 indicates the heterocycle of general formula (R1-10)
In formula:
- R29 can be hydrogen atom, halogen atom, amino, cyano, C1-C4- alkyl amino, two-(C1-C4- alkyl) ammonia Base, C1-C4- alkyl, the C1-C4- halogenated alkyl with 1 to 5 halogen atoms, or optionally by halogen atom or C1-C4- alkyl Substituted phenyl；
- R30 can be halogen atom, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-11)
In formula:
- R31 can be hydrogen atom, halogen atom, amino, cyano, C1-C4- alkyl amino, two-(C1-C4- alkyl) ammonia Base, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms；
- R32 can be halogen atom, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-12)
In formula:
- R33 can be halogen atom, cyano, nitro, C1-C4- alkyl, the C1-C4- halogen with 1 to 5 halogen atoms Substituted alkyl, C3-C6- naphthenic base, C1-C4- alkoxy, C1-C4- halogenated alkoxy, C1-C4- with 1- to 5 halogen atom Alkylthio group, the C1-C4- halogenated alkylthio with 1 to 5 halogen atoms, amino carbonyl or amino carbonyl-C1-C4- alkyl；
- R34 can be hydrogen atom, halogen atom, cyano, nitro, C1-C4- alkyl, C1-C4- alkoxy or C1-C4- alkane Sulfenyl；
- R35 can be hydrogen atom, phenyl, C1-C4- alkyl, the C1-C4- halogenated alkyl with 1 to 5 halogen atoms, Hydroxyl-C1-C4- alkyl, C3-C6- naphthenic base, C1-C4- alkylthio group-C1-C4- alkyl, has 1 to 5 halogen at C2-C6- alkenyl C1-C4- halogenated alkylthio-C1-C4- the alkyl of plain atom, C1-C4- alkoxy -C 1-C4- alkyl have 1 to 5 halogen originals C1-C4- halogenated alkoxy-C1-C4- the alkyl of son.
R1 indicates the heterocycle of general formula (R1-13)
In formula:
- R36 can be hydrogen atom, halogen atom, cyano, nitro, C1-C4- alkyl, with 1 to 5 halogen atoms C1-C4- halogenated alkyl, C3-C6- naphthenic base, C1-C4- alkoxy, the C1-C4- haloalkoxy with 1- to 5 halogen atom Base, C1-C4- alkylthio group, the C1-C4- halogenated alkylthio with 1 to 5 halogen atoms, amino carbonyl or amino carbonyl-C1- C4- alkyl；
- R37 can be hydrogen atom, halogen atom, cyano, C1-C4- alkyl, C1-C4- alkoxy, have 1 to 5 halogens The C1-C4- halogenated alkoxy or C1-C4- alkylthio group of atom；
- R38 can be hydrogen atom, C1-C4- alkyl, C1-C4- halogenated alkyl, hydroxyl-with 1 to 5 halogen atoms C1-C4- alkyl, C3-C6- naphthenic base, C1-C4- alkylthio group-C1-C4- alkyl, has 1 to 5 halogen atoms at C2-C6- alkenyl C1-C4- halogenated alkylthio-C1-C4- alkyl, C1-C4- alkoxy -C 1-C4- alkyl, the C1- with 1 to 5 halogen atoms C4- halogenated alkoxy-C1-C4- alkyl is optionally taken by halogen atom, C1-C4- alkyl, C1-C4- alkoxyalkyl or nitro The phenyl in generation；
R1 indicates the heterocycle of general formula (R1-14)
In formula:
- R39 can be hydrogen atom, halogen atom, cyano, nitro, C1-C4- alkyl, with 1 to 5 halogen atoms C1-C4- halogenated alkyl, C3-C6- naphthenic base, C1-C4- alkoxy, the C1-C4- haloalkoxy with 1- to 5 halogen atom Base, C1-C4- alkylthio group, the C1-C4- halogenated alkylthio with 1 to 5 halogen atoms, amino carbonyl or amino carbonyl-C1- C4- alkyl；
- R40 can be hydrogen atom, halogen atom, cyano, C1-C4- alkyl, C1-C4- alkoxy, C1-C4- alkylthio group or C1-C4- halogenated alkyl with 1 to 5 halogen atoms；
It is halogenated that-R41 can be hydrogen atom, phenyl, benzyl, C1-C4- alkyl, the C1-C4- with 1 to 5 halogen atoms Alkyl, C2-C6- alkenyl, C3-C6- naphthenic base, C1-C4- alkylthio group-C1-C4- alkyl, has 1 to 5 at hydroxyl-C1-C4- alkyl C1-C4- halogenated alkylthio-C1-C4- the alkyl of a halogen atom, has 1 to 5 halogen at C1-C4- alkoxy -C 1-C4- alkyl C1-C4- halogenated alkoxy-C1-C4- the alkyl of plain atom.
R1 indicates the heterocycle of general formula (R1-15)
In formula:
It is halogenated that-R42 can be hydrogen atom, halogen atom, C1-C4- alkyl or C1-C4- with 1 to 5 halogen atoms Alkyl.
- R43 can be halogen atom, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-16)
In formula:
- R44 and R45 can be identical or different, can be hydrogen atom, halogen atom, C1-C4- alkyl, has 1 to 5 halogen The C1-C4- halogenated alkyl of plain atom, optionally by halogen atom or the alkyl-substituted phenyl of C1-C4-, or optionally by halogen atom Or the alkyl-substituted heterocycle of C1-C4-.
R1 indicates the heterocycle of general formula (R1-17)
In formula:
- R46 can be halogen atom, C1-C4 alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms；
- R47 can be halogen atom, C1-C4 alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-18)
In formula:
- R48 can be halogen atom, C1-C4 alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-19)
In formula:
- R49 can be halogen atom, C1-C4 alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms；
- R50 can be hydrogen atom, C1-C4- alkyl, the C1-C4- halogenated alkyl with 1 to 5 halogen atoms or optionally By halogen atom or the alkyl-substituted phenyl of C1-C4-.
R1 indicates the heterocycle of general formula (R1-20)
In formula:
- R51 can be halogen atom, C1-C4 alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 in compounds of formula I can be the hexa-member heterocycle in addition to phenyl ring, and wherein R1 is six in addition to phenyl ring The specific example of circle heterocyclic ring includes:
R1 indicates the heterocycle of general formula (R1-21)
In formula:
It is halogenated that-R52 can be halogen atom, hydroxyl, cyano, C1-C4 alkyl, the C1-C4- with 1 to 5 halogen atoms Alkyl, C1-C4- alkoxy, C1-C4- alkylthio group, the C1-C4- halogenated alkylthio with 1 to 5 halogen atoms have 1 to 5 The C1-C4- halogenated alkoxy of a halogen atom；
- R53, R54 and R55 may be the same or different, and can be hydrogen atom, halogen atom, cyano, C1-C4- alkyl, have 1 To the C1-C4- halogenated alkyl of 5 halogen atoms, C1-C4- alkoxy, C1-C4- alkylthio group, with 1 to 5 halogen atoms C1-C4- halogenated alkoxy, C1-C4- alkyl sulphinyl or C1-C4- alkyl sulphonyl.
R1 indicates the heterocycle of general formula (R1-22)
In formula:
- R56 can be hydrogen atom, halogen atom, hydroxyl, cyano, C1-C4 alkyl, the C1- with 1 to 5 halogen atoms C4- halogenated alkyl, C1-C4- alkoxy, C1-C5- alkylthio group, C2-C5- alkenylthio group,.C1- with 1 to 5 halogen atoms C4- halogenated alkylthio, the C1-C4- halogenated alkoxy with 1 to 5 halogen atoms, optionally by halogen atom or C1-C4- alkyl Substituted phenoxy group, or optionally by halogen atom or the alkyl-substituted thiophenyl of C1-C4-；
- R57, R58 and R59 may be the same or different, and can be hydrogen atom, halogen atom, cyano, C1-C4- alkyl, have 1 To the C1-C4- halogenated alkyl of 5 halogen atoms, C1-C4- alkoxy, C1-C4- alkylthio group, with 1 to 5 halogen atoms C1-C4- halogenated alkoxy, C1-C4- alkyl sulphinyl, C1-C4- alkyl sulphonyl or optionally by halogen atom or C1-C4 alkane The N- morpholine that base replaces, or optionally by halogen atom or the alkyl-substituted thienyl of C1-C4-.
R1 indicates the heterocycle of general formula (R1-23)
In formula:
- R60, R61, R62 and R63 may be the same or different, and can be hydrogen atom, halogen atom, hydroxyl, cyano, C1-C4- Alkyl, C1-C4- alkoxy, C1-C4- alkylthio group, has 1 to 5 at the C1-C4- halogenated alkyl with 1 to 5 halogen atoms The C1-C4- halogenated alkylthio of halogen atom, the C1-C4- halogenated alkoxy with 1 to 5 halogen atoms, C1-C4- alkyl are sub- Sulfonyl or C1-C4- alkyl sulphonyl；
R1 indicates the heterocycle of general formula (R1-24)
In formula:
- R64 can be halogen atom, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms；
- R65 can be hydrogen atom, C1-C4- alkyl, C1-C4- halogenated alkyl, C1-C6- with 1 to 5 halogen atoms Alkoxy carbonyl, appoints selected 1 to 3 halogen atoms or substituted benzyloxy at the benzyl optionally replaced by 1 to 3 halogen atoms Carbonyl or heterocycle.
R1 indicates the heterocycle of general formula (R1-25)
In formula:
- R66 can be halogen atom, hydroxyl, cyano, C1-C4- alkyl, the C1-C4- halogen with 1 to 5 halogen atoms Substituted alkyl, C1-C4- alkoxy, C1-C4- alkylthio group, the C1-C4- halogenated alkylthio with 1 to 5 halogen atoms have 1 To the C1-C4- halogenated alkoxy of 5 halogen atoms；
- R67 can be hydrogen atom, C1-C4- alkyl, C1-C4- halogenated alkyl or benzyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-26)
In formula:
- X1 can be sulphur atom ,-SO- ,-SO2Or-CH2-；
- R68 can be C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms；
- R69 and R70 may be the same or different, and can be hydrogen atom or C1-C4- alkyl.
R1 indicates the heterocycle of general formula (R1-27)
In formula:
- R71 can be C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-28)
In formula:
- R72 can be C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-29)
In formula:
- R73 can be halogen atom, C1-C4- alkyl or the C1-C4- halogenated alkyl with 1 to 5 halogen atoms.
According to the present invention, the R1 for leading to the compound of formula (I) can be condensed ring.Wherein R1 is the compounds of this invention of condensed ring Specific example includes:
R1 indicates the heterocycle of general formula (R1-30)
In formula:
- R74 ,-R75 ,-R76 ,-R77 ,-R78 ,-R79 can be hydrogen atom, halogen atom, C1-C4- alkyl or have 1 To the C1-C4- halogenated alkyl of 5 halogen atoms, C1-C4- alkoxy or C1-C4- alkyl halide with 1 to 5 halogen atoms Oxygroup.
R1 indicates the heterocycle of general formula (R1-31)
In formula:
It is halogenated that-R80 can be hydrogen atom, halogen atom, C1-C4- alkyl or C1-C4- with 1 to 5 halogen atoms Alkyl, C1-C4- alkoxy or the C1-C4- halogenated alkoxy with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-32)
In formula:
It is halogenated that-R81 can be hydrogen atom, halogen atom, C1-C4- alkyl or C1-C4- with 1 to 5 halogen atoms Alkyl, C1-C4- alkoxy or the C1-C4- halogenated alkoxy with 1 to 5 halogen atoms.
R1 indicates the heterocycle of general formula (R1-33)
In formula:
It is halogenated that-R82 can be hydrogen atom, halogen atom, C1-C4- alkyl or C1-C4- with 1 to 5 halogen atoms Alkyl, C1-C4- alkoxy or the C1-C4- halogenated alkoxy with 1 to 5 halogen atoms.
Compounds of formula I includes the transconfiguration of Formula II:
The compound that Formulas I and Formula II indicate is especially right to the ovum and second instar larvae of root-knot nematode also good control efficiency It is excellent in the hatching effect of the root-knot nematode eggs such as inhibition cucumber, tomato, tobacco, soybean.
The compound synthesis method that the present invention refers to is known to those skilled in the art.The present invention provides following real It applies example and illustrates that the various aspects of the compounds of this invention but should not be understood as limitations on claims.
The compound of the present invention can be expressed by following synthesis general formula: the following method of compound that formula 1 represents It synthesizes, in a solvent with butyl bromide halogen substituents, generate ester under the action of alkaline matter is one very classical to acid Synthetic method, common solvent are n,N-Dimethylformamide, acetone, ethyl alcohol equal solvent, and alkali can be inorganic base, be also possible to Organic base.It generally can be with following reaction equation come the synthesis of expression I:
The compound of Formula II can be synthesized with following methods:
The racemic acid of cis-trans, can take following methods to be converted to transconfiguration acid, and method is that will disappear outside cis-trans The acid of rotation is added in acid solution, and 4~8h is stirred at 45~60 DEG C, and obtaining cis and trans structure proportion is 1:9 mixture, Cold filtration, obtained solid matter is re-dissolved in ethyl acetate, and is washed with water, dried over magnesium sulfate, evaporates solvent, uses first Benzene recrystallization, it is dry, obtain the compound of transconfiguration (structure is as shown in Formula II).
The part of compounds list of the nematicide (Formulas I) of structure novel of the invention is as shown in table 1.
The part of compounds list of 1 Formulas I of table
The part of compounds list of the nematicide (Formula II) of structure novel of the invention is as shown in table 2.
The part of compounds list of 2 Formula II of table
Embodiment 1
When R1 isWhen R2 is fluorine atom, the structural formula for the compound (compound 3) that formula 1 represents and synthesis Method is as follows:
The preparation of step 1:2- (heptane -3- base) -5- oxygen tetrahydrofuran -3- carboxylic acid
25.6g 2- ethyl hexanal, 25.0g succinic anhydride, 59.8g anhydrous zinc chloride and the anhydrous 1,2- of 300ml in 1L reaction kettle Dichloroethanes.Stirring is cooled to 2 DEG C, and 40.4g triethylamine is added dropwise, then heats to 40 DEG C and is stirred to react 12h, and reaction terminates, to In kettle plus water 200g, addition concentrated hydrochloric acid 43.7g, stirring, stratification, water layer 200ml 1, the extraction of 2- dichloroethanes merge Organic layer adds water 50g washing three times, and organic phase takes off dry solvent, to the residual middle addition toluene 80g of kettle, is warming up to reflux, decrease temperature crystalline, Filtering, is dried to obtain 2- (heptane -3- base) -5- oxygen tetrahydrofuran -3- carboxylic acid 34.2g, cis/trans ratios 28:72, yield 75%.
Step 2: the preparation of compound 3
Bromo- 1, the 1- bis- of 2- (heptane -3- base) -5- oxygen tetrahydrofuran -3- carboxylic acid 22.8g, 4- is added in 500ml four-hole boiling flask Fluoro- 1- butylene 28.4g, Anhydrous potassium carbonate 20.7g, acetonitrile 150g, back flow reaction for 24 hours, finish by reaction, filters, filtrate negative pressure steams Solvent acetonitrile, residue add methylene chloride 100ml dissolved product, and water 50ml is added to wash, and vacuum distillation goes out methylene chloride, kettle Bottom residue is product 28.6g.Mass Spectrometer Method: 336.15 (100.0%), 337.16 (17.7%), 338.16 (2.3%)；Member Element analysis: C, 57.13；H, 6.89；F, 16.95；O, 19.03.
Embodiment 2
When R1 isWhen R6 is fluorine atom, compound (compound 6) structural formula and synthesis side that Formulas I represents Method is as follows:
The preparation of step 1:2- (furans -2- base) -5- oxygen tetrahydrofuran -3- carboxylic acid
19.2g 2 furan carboxyaldehyde, 25.0g succinic anhydride, 59.8g anhydrous zinc chloride and the anhydrous 1,2- of 300ml in 1L reaction kettle Dichloroethanes.Stirring is cooled to 2 DEG C, and 40.4g triethylamine is added dropwise, then heats to 40 DEG C and is stirred to react 12h, and reaction terminates, to In kettle plus water 200g, addition concentrated hydrochloric acid 43.7g, stirring, stratification, water layer 200ml 1, the extraction of 2- dichloroethanes merge Organic layer adds water 50g washing three times, and organic phase takes off dry solvent, to the residual middle addition toluene 80g of kettle, is warming up to reflux, decrease temperature crystalline, Filtering, is dried to obtain 2- (furans -2- base) -5- oxygen tetrahydrofuran -3- carboxylic acid 31.4g, cis/trans ratios 27:73, yield 80%.
Step 2: the preparation of compound 6
2- (furans -2- base) -5- oxygen tetrahydrofuran -3- carboxylic acid 19.6g, 4- bromo- 1,1,2- is added in 500ml four-hole boiling flask Three fluoro- 1- butylene 28.4g, Anhydrous potassium carbonate 20.7g, acetonitrile 150g, back flow reaction for 24 hours, finish by reaction, filters, filtrate negative pressure is steamed Solvent out, residue add methylene chloride 100ml dissolved product, and water 50ml is added to wash, and vacuum distillation goes out methylene chloride, bottom Residue is product 27.4g.Mass Spectrometer Method: 304.06 (100.0%), 305.06 (14.4%), 306.06 (2.0%)；Element Analysis: C, 51.32；H, 3.64；F, 18.73；O, 26.30.
Embodiment 3
When R1 isWhen R6 is fluorine atom, the structural formula for the compound (compound 38) that formula 1 represents and synthesis side Method is as follows:
The preparation of step 1:2- (pyridin-3-yl) -5- oxygen tetrahydrofuran -3- carboxylic acid
21.4g cigarette aldehyde, 25.0g succinic anhydride, 59.8g anhydrous zinc chloride and anhydrous bis- chloroethene of 1,2- of 300ml in 1L reaction kettle Alkane.Stirring is cooled to 2 DEG C, and 40.4g triethylamine is added dropwise, then heats to 40 DEG C and is stirred to react 12h, and reaction terminates, and adds into kettle Concentrated hydrochloric acid 43.7g is added in water 200g, stirs, stratification, and the extraction of water layer 200ml1,2- dichloroethanes merges organic layer and adds Water 50g is washed three times, and organic phase takes off dry solvent, to the residual middle addition toluene 80g of kettle, is warming up to reflux, and decrease temperature crystalline filters, and does It is dry to obtain 2- (pyridin-3-yl) -5- oxygen tetrahydrofuran -3- carboxylic acid 30.2g, cis/trans ratios 25:75, yield 73%.
Step 2: the preparation of compound 38
2- (pyridin-3-yl) -5- oxygen tetrahydrofuran -3- carboxylic acid 20.7g, 4- bromo- 1,1,2- is added in 500ml four-hole boiling flask Three fluoro- 1- butylene 28.4g, Anhydrous potassium carbonate 20.7g, acetonitrile 150g, back flow reaction for 24 hours, finish by reaction, filters, filtrate negative pressure is steamed Solvent out, residue add methylene chloride 100ml dissolved product, and water 50ml is added to wash, and vacuum distillation goes out methylene chloride, bottom Residue is product 27.7g.Mass Spectrometer Method: m/z:315.07 (100.0%), 316.08 (15.4%), 317.08 (1.9%)； Elemental analysis: C, 53.34；H, 3.84；F, 18.08；N, 4.44；O, 20.30.
Embodiment 4
When R1 isWhen R6 is fluorine atom, compound (compound 55) and its synthesis side that Formulas I represents Method is as follows:
The preparation of step 1:2- (quinoline -2- base) -5- oxygen tetrahydrofuran -3- carboxylic acid
31.4g 2- quinoline aldehyde, 25.0g succinic anhydride, 59.8g anhydrous zinc chloride and the anhydrous 1,2- of 300ml in 1L reaction kettle Dichloroethanes.Stirring is cooled to 2 DEG C, and 40.4g triethylamine is added dropwise, then heats to 40 DEG C and is stirred to react 12h, and reaction terminates, to In kettle plus water 200g, addition concentrated hydrochloric acid 43.7g, stirring, stratification, water layer 200ml 1, the extraction of 2- dichloroethanes merge Organic layer adds water 50g washing three times, and organic phase takes off dry solvent, to the residual middle addition toluene 80g of kettle, is warming up to reflux, decrease temperature crystalline, Filtering, is dried to obtain 2- (quinoline -2- base) -5- oxygen tetrahydrofuran -3- carboxylic acid 37.0g, cis/trans ratios 27:73, yield 72%.
Step 2: the preparation of compound 55
2- (quinoline -2- base) -5- oxygen tetrahydrofuran -3- carboxylic acid 25.7g, 4- bromo- 1,1,2- is added in 500ml four-hole boiling flask Three fluoro- 1- butylene 28.4g, Anhydrous potassium carbonate 20.7g, acetonitrile 150g, back flow reaction for 24 hours, finish by reaction, filters, filtrate negative pressure is steamed Solvent out, residue add methylene chloride 100ml dissolved product, and water 50ml is added to wash, and vacuum distillation goes out methylene chloride, bottom Residue is product 31.4g.Mass Spectrometer Method: 365.09 (100.0%), 366.09 (19.8%), 367.09 (2.7%) elements point Analysis: C, 59.18；H, 3.86；F, 15.60；N, 3.83；O, 17.52.
Embodiment 5
The structural formula of compound 63 and the preparation method is as follows:
2 method and step 1 of reference implementation example obtains 2- (furans -2- base) -5- oxygen tetrahydrofuran -3- carboxylic acid 31.4g, cis-/ Trans ratios are 27:73, carry out configuration conversion below.
The racemic acid 31.4g of cis-trans is added in 500ml reaction kettle, 1,2- dichloroethanes 200g again is added, is added The hydrochloric acid of 50g20% is heated to 45 DEG C of stirring 12h, and conversion terminates, stratification, and organic addition water 50g washing is three times, organic Dry solvent is mutually taken off, with re crystallization from toluene, being dried to obtain solid matter is transconfiguration acid 28.3g, cis/trans ratios 0.5: 99.5.Configuration conversion yields 90%.
2 step 2 of reference implementation example obtains target compound 28.6g.Mass Spectrometer Method: 304.06 (100.0%), 305.06 (14.4%), 306.06 (2.0%)；Elemental analysis: C, 51.32；H, 3.64；F, 18.73；O, 26.30.
Part of compounds in Tables 1 and 2 is carried out to inhibit plant pathogeny line insect test using dip method, more than measurement Compound surveys the activity of second instar larvae referring concurrently to NY/T 1154.5-2006 (the 5th part: ovicidal activity tests infusion process) The above compound is tried to the inhibitory activity of nematode egg hatching, the results are shown in Table 3:
3 compound of table inhibits plant pathogeny line insect test result
The nematicide of structure novel of the invention is equal to nematode second instar larvae and worm's ovum it can be seen from the result of table 3 There is preferable control efficiency.

Claims (8)

1. a kind of nematicide of structure novel, it is characterised in that: structure is shown in formula I:
Wherein, R1For the aliphatic hydrocarbon of C1-C16, five-ring heterocycles, hexa-member heterocycle or condensed ring in addition to phenyl ring；R2For hydrogen atom or halogen Plain atom.
2. a kind of nematicide of structure novel according to claim 1, it is characterised in that: R1For ethyl, propyl,
3. a kind of nematicide of structure novel according to claim 1, it is characterised in that: R1For
4. a kind of nematicide of structure novel according to claim 1, it is characterised in that: R1For
5. a kind of nematicide of structure novel according to claim 1, it is characterised in that: R1For
6. a kind of nematicide of structure novel according to claim 1, it is characterised in that: R2For fluorine atom.
7. a kind of nematicide of structure novel according to claim 1, it is characterised in that: include in the compound of Formulas I Transconfiguration shown in Formula II, specific structural formula are as follows:
8. a kind of purposes of the nematicide of structure novel described in claim 1, it is characterised in that: for preventing and treating agricultural crops On root-knot nematode.
CN201810939874.1A 2018-08-17 2018-08-17 A kind of nematicide of structure novel and application thereof Pending CN109020928A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111149808A (en) * 2020-01-10 2020-05-15 云南农业大学 Application of furan cyclo-pyran ring compound in preparation of nematocide
WO2020222118A1 (en) * 2019-04-30 2020-11-05 Isagro S.P.A. Esters of non- aromatic heterocyclic compounds having a nematocidal activity, their agronomic compositions and use thereof.
CN113912495A (en) * 2020-07-09 2022-01-11 山东省联合农药工业有限公司 Fluorine-containing butylene ester derivative and preparation method and application thereof
CN114075300A (en) * 2020-08-21 2022-02-22 佛山市海力盈生物科技有限公司 Novel chitosan oligosaccharide derivative nematocide and preparation method and application thereof

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CN106554334A (en) * 2015-09-30 2017-04-05 山东省联合农药工业有限公司 A kind of nematicide containing lactonic ring and its production and use

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CN106554334A (en) * 2015-09-30 2017-04-05 山东省联合农药工业有限公司 A kind of nematicide containing lactonic ring and its production and use

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020222118A1 (en) * 2019-04-30 2020-11-05 Isagro S.P.A. Esters of non- aromatic heterocyclic compounds having a nematocidal activity, their agronomic compositions and use thereof.
CN113784952A (en) * 2019-04-30 2021-12-10 伊萨格罗股份公司 Esters of non-aromatic heterocyclic compounds with nematicidal activity, their agronomic compositions and uses thereof
CN111149808A (en) * 2020-01-10 2020-05-15 云南农业大学 Application of furan cyclo-pyran ring compound in preparation of nematocide
CN111149808B (en) * 2020-01-10 2021-05-07 云南农业大学 Application of furan cyclo-pyran ring compound in preparation of nematocide
CN113912495A (en) * 2020-07-09 2022-01-11 山东省联合农药工业有限公司 Fluorine-containing butylene ester derivative and preparation method and application thereof
CN114075300A (en) * 2020-08-21 2022-02-22 佛山市海力盈生物科技有限公司 Novel chitosan oligosaccharide derivative nematocide and preparation method and application thereof
CN114075300B (en) * 2020-08-21 2023-02-28 佛山市海力盈生物科技有限公司 Chitosan oligosaccharide derivative nematicide and preparation method and application thereof

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Application publication date: 20181218