CN105777733B - A kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline - Google Patents

A kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline Download PDF

Info

Publication number
CN105777733B
CN105777733B CN201410782605.0A CN201410782605A CN105777733B CN 105777733 B CN105777733 B CN 105777733B CN 201410782605 A CN201410782605 A CN 201410782605A CN 105777733 B CN105777733 B CN 105777733B
Authority
CN
China
Prior art keywords
alkyl
carbonyl
hydrogen
alkoxy
halogenated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201410782605.0A
Other languages
Chinese (zh)
Other versions
CN105777733A (en
Inventor
杨吉春
吴峤
崔东亮
关爱莹
卢政茂
***
刘长令
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shenyang Sinochem Agrochemicals R&D Co Ltd
Original Assignee
Shenyang Sinochem Agrochemicals R&D Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shenyang Sinochem Agrochemicals R&D Co Ltd filed Critical Shenyang Sinochem Agrochemicals R&D Co Ltd
Priority to CN201410782605.0A priority Critical patent/CN105777733B/en
Publication of CN105777733A publication Critical patent/CN105777733A/en
Application granted granted Critical
Publication of CN105777733B publication Critical patent/CN105777733B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention belongs to field of agricultural herbicide, and in particular to a kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline.Tetrahydric phthalimide class compound containing isoxazoline is as shown in logical formula (I), logical formula (I) compound has good activity of weeding, the weeds such as youth-and-old-age, piemarker, herba setariae viridis, barnyard grass can be efficiently controlled, good herbicidal effect is obtained under low dosage, and there is preferable safety to crop such as corn, wheat, rice etc., it agriculturally can be used as herbicide.

Description

A kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline
Technical field
The invention belongs to field of agricultural herbicide, and in particular to a kind of tetrahydric phthalimide class containing isoxazoline Compound and application thereof.
Background technique
The exploitation of tetrahydric phthalimide class herbicide is more early, multi-purpose to make dry land herbicide, although research in recent years compared with It is few, but also when have patent report, as Nissan Chemical Industries is public in patent JP2229157, JP1139581 The structure of following general formula is opened.However these known compounds are not always to be entirely satisfactory for the preventive effect of weeds.
Wherein: Q1 is five-ring heterocycles such as oxadiazoles, oxazole or benzoxazoles etc..Q2 is F or H.
In the prior art, though disclosed compound has certain similarity, general formula of the present invention with the compounds of this invention Compound represented and the prior art have significant difference, and all have good activity of weeding.
Summary of the invention
In order to which development of new herbicide is to solve the problems, such as the Herbicid resistant got worse, the present invention provides a kind of containing different evil Tetrahydric phthalimide class compound of oxazoline and application thereof.
To achieve the above object, The technical solution adopted by the invention is as follows:
The present invention provides a kind of tetrahydric phthalimide class compound containing isoxazoline, as shown in logical formula (I):
In formula:
R1、R2、R3、R4It is respectively selected from hydrogen, halogen, C1-C6Alkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkane Sulfenyl or C1-C6Alkyl sulphonyl；
R5、R6It is respectively selected from hydrogen, cyano, C1-C6Alkyl, CO2R9、CH2OR10, phenyl or following base is independently selected from by 1-4 The phenyl that group replaces: halogen, CN, NO2、C1-C8Alkyl, C1-C8Halogenated alkyl, C1-C8Alkoxy, C1-C8Halogenated alkoxy, C1- C8Alkoxy carbonyl, C1-C8Alkylthio group or C1-C8Alkyl sulphonyl；
R7、R8It is respectively selected from hydrogen, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, CO2R9、CH2OR10、CH2NR11R12、 CONR11R12, phenyl or the phenyl that following group replaces: halogen, CN, NO is independently selected from by 1-42、C1-C4Alkyl, C1-C4Halogen Substituted alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group or C1-C4Alkyl sulphonyl；
R9Selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Alkenyl, C3-C6Alkynyl, C1-C6Alkoxy C1-C6Alkane Base, C1-C6Alkyl carbonyl oxygroup C2-C6Alkyl, benzyl unsubstituted or that following group is independently selected from by 1-4: halogen, CN, NO2、C1-C8Alkyl, C1-C8Halogenated alkyl, C1-C8Alkoxy, C1-C8Halogenated alkoxy, C1-C8Alkoxy carbonyl, C1-C8Alkane sulphur Base, C1-C8Alkyl sulphonyl；
R10Selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy carbonyl, C1-C6Alkyl-carbonyl, C1-C6Halogen Fluoroalkylcarbonyl, C3-C6Naphthene base carbonyl, C3-C6Halogenated cycloalkyl carbonyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulphonyl Base, C1-C6Alkyl amino sulfonyl, two (C1-C6) alkyl amino sulfonyl, C1-C6Alkyl amino-carbonyl, two (C1-C6) alkyl ammonia Base carbonyl, two (C1-C6) thio-alkyl amino-carbonyl, C1-C6Alkylthio group C2-C6Alkyl-carbonyl, it is unsubstituted or independent by 1-4 Phenyl, phenyl C selected from following group1-C2Alkyl, phenyl C2-C4Alkenyl, phenylcarbonyl group, phenyl C1-C2Alkyl-carbonyl, benzene oxygen Base C1-C2Alkyl-carbonyl, phenyl C2-C4Alkenyl carbonyl, heteroaryl, heteroaryl C1-C2Alkyl, Heteroarylcarbonyl: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkane sulphur Base, C1-C4Alkyl sulphonyl or by 1-4 halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4 The phenoxy group that halogenated alkoxy independently replaces；
R11、R12It is respectively selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy carbonyl C1-C6Alkyl；And R11、 R12Five yuan or hexatomic ring can be connected to form by N.
The more preferred compound of the present invention are as follows: in logical formula (I)
R1、R2、R3、R4It is respectively selected from hydrogen, halogen, C1-C6Alkyl or C1-C6Alkoxy；
R5Selected from hydrogen or C1-C6Alkyl；
R6Selected from hydrogen, C1-C6Alkyl, CO2R9Or CH2OR10；
R7Selected from hydrogen, cyano, C1-C6Alkyl, CO2R9、CH2OR10、CH2NR11R12Or CONR11R12；
R8Selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, phenyl are independently selected from the benzene that following group replaces by 1-4 Base: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl Base, C1-C4Alkylthio group or C1-C4Alkyl sulphonyl；
R9Selected from hydrogen, C1-C6Alkyl, C3-C4Alkenyl, C3-C4Alkynyl, C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkyl carbonyl oxygen Base C2-C3Alkyl, it is unsubstituted or the benzyl that following group replaces: halogen, CN, NO is independently selected from by 1-42、C1-C6Alkyl or C1-C6Halogenated alkyl；
R10Selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy carbonyl, C1-C6Alkyl-carbonyl, C1-C6It is halogenated Alkyl-carbonyl, C3-C6Naphthene base carbonyl, C3-C6Halogenated cycloalkyl carbonyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulphonyl Base, C1-C6Alkyl amino sulfonyl, two (C1-C6) alkyl amino sulfonyl, C1-C6Alkyl amino-carbonyl, two (C1-C6) alkyl ammonia Base carbonyl, two (C1-C6) thio-alkyl amino-carbonyl, C1-C6Alkylthio group C2-C6Alkyl-carbonyl, it is unsubstituted or independent by 1-4 The phenyl C replaced selected from following group1-C2Alkyl, phenylcarbonyl group, phenyl C1-C2Alkyl-carbonyl, phenyl C2-C4Alkenyl carbonyl, benzene Oxygroup C1-C2Alkyl-carbonyl, thiophenecarbonyl groups, pyrazoles carbonyl, quinolinecarbonyl: halogen, CN, NO2、C1-C4Alkyl, C1-C4Alkyl halide Base, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4Alkyl sulphonyl or by 1- 4 halogens, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4The benzene that halogenated alkoxy independently replaces Oxygroup；
R11、R12It is respectively selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；Alternatively, R11、R12Five yuan or hexatomic ring can be connected to form by N.
The further preferred compound of the present invention are as follows: in logical formula (I)
R1、R2、R3、R4It is respectively selected from hydrogen, halogen or C1-C4Alkyl；
R5Selected from hydrogen or C1-C4Alkyl；
R6Selected from hydrogen, C1-C4Alkyl, CO2R9Or CH2OR10；
R7Selected from hydrogen, cyano, C1-C4Alkyl, CO2R9、CH2OR10、CH2NR11R12Or CONR11R12；
R8Selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl, phenyl are independently selected from the benzene that following group replaces by 1-4 Base: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl Base, C1-C4Alkylthio group or C1-C4Alkyl sulphonyl；
R9Selected from hydrogen, C1-C4Alkyl, C3-C4Alkenyl, C3-C4Alkynyl, C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkyl carbonyl oxygen Base C2-C4Alkyl, benzyl unsubstituted or that following group is independently selected from by 1-4: halogen, CN, NO2、C1-C4Alkyl or C1- C4Halogenated alkyl；
R10Selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl, C1-C4Halogen Fluoroalkylcarbonyl, C3-C6Naphthene base carbonyl, C3-C6Halogenated cycloalkyl carbonyl, C1-C4Alkyl sulphonyl, C1-C4Halogenated alkyl sulphonyl Base, C1-C3Alkyl amino sulfonyl, two (C1-C3) alkyl amino sulfonyl, C1-C3Alkyl amino-carbonyl, two (C1-C3) alkyl ammonia Base carbonyl, two (C1-C3) thio-alkyl amino-carbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl, it is unsubstituted or independent by 1-4 Phenyl C selected from following group1-C2Alkyl, phenylcarbonyl group, phenyl C1-C2Alkyl-carbonyl, phenyl C2-C4Alkenyl carbonyl, phenoxy group C1-C2Alkyl-carbonyl, thiophenecarbonyl groups, pyrazoles carbonyl or quinolinecarbonyl: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4Alkyl sulphonyl is a by 1-4 Halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4The benzene oxygen that halogenated alkoxy independently replaces Base；
R11、R12It is respectively selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；And R11、 R12Five yuan or hexatomic ring can be connected to form by N.
The more more preferred compound of the present invention are as follows: in logical formula (I)
R1、R2、R3、R4It is respectively selected from hydrogen, fluorine, chlorine or methyl；
R5Selected from hydrogen or methyl；
R6Selected from hydrogen, methyl, CO2R9Or CH2OR10；
R7Selected from hydrogen, cyano, methyl, ethyl, CO2R9、CH2OR10、CH2NR11R12Or CONR11R12；
R8Selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl, phenyl are independently selected from the benzene that following group replaces by 1-4 Base: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4Halogenated alkoxy；
R9Selected from hydrogen, C1-C4Alkyl, allyl, propargyl, C1-C3Alkoxy C1-C3Alkyl, C1-C4Alkyl carbonyl oxygroup C2- C3Alkyl, benzyl unsubstituted or that following group is independently selected from by 1-4: halogen, CN, NO2Or C1-C4Alkyl；
R10Selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl, C1-C4It is halogenated Alkyl-carbonyl, C3-C6Naphthene base carbonyl, C1-C4Alkyl sulphonyl, C1-C4Halogenated alkyl sulfonyl, two (C1-C2) alkyl amino sulphur Acyl group, C1-C2Alkyl amino-carbonyl, two (C1-C3) alkyl amino-carbonyl, two (C1-C2) thio-alkyl amino-carbonyl, C1-C2Alkane sulphur Base C2-C4Alkyl-carbonyl, phenylcarbonyl group, phenyl C unsubstituted or that following group is independently selected from by 1-41-C2Alkyl-carbonyl, Phenoxy group C1-C2Alkyl-carbonyl, thiophenecarbonyl groups, quinolinecarbonyl or pyrazoles carbonyl: halogen, CN, NO2、C1-C4Alkyl, C1-C4It is halogenated Alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4Alkyl sulphonyl or 2- Chloro-trifluoromethyl phenoxy；
R11、R12It is respectively selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；And R11、 R12Five yuan or hexatomic ring can be connected to form by N.
The present invention more preferred compound again are as follows: in logical formula (I)
R1、R2It is respectively selected from hydrogen, fluorine, chlorine or methyl；
R3、R4It is respectively selected from hydrogen；
R5Selected from hydrogen or methyl；
R6Selected from hydrogen, methyl, CO2R9Or CH2OR10；
R7Selected from hydrogen, cyano, methyl, ethyl, CO2R9、CH2OR10Or CONR11R12；
R6、R7It is not simultaneously CO2R9Or CH2OR10；
R8Selected from hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, phenyl or following group is independently selected from by 1-4 takes The phenyl in generation: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4Halogenated alkoxy；
R9Selected from hydrogen, methyl, ethyl, n-propyl, normal-butyl, isopropyl, tert-butyl, allyl, propargyl, methoxyl group second Base, ethoxyethyl group or methyl carbonyl oxygroup ethyl；
R10Selected from hydrogen, C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl, C1-C4Halogenated alkyl carbonyl, C3-C6Naphthenic base carbonyl Base, C1-C4Alkyl sulphonyl, C1-C4Halogenated alkyl sulfonyl, two (C1-C2) alkyl amino sulfonyl, C1-C2Alkyl amino carbonyl Base, two (C1-C3) alkyl amino-carbonyl, two (C1-C2) thio-alkyl amino-carbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl does not take Generation or phenylcarbonyl group, the phenyl C that following group is independently selected from by 1-41-C2Alkyl-carbonyl, phenoxy group C1-C2Alkyl-carbonyl, Quinolinecarbonyl or thiophenecarbonyl groups: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Haloalkoxy Base, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4Alkyl sulphonyl or 2- chloro-trifluoromethyl phenoxy；
R11Selected from hydrogen, C1-C4Alkyl or C1-C4Halogenated alkyl；
R12Selected from hydrogen, C1-C4Alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；
R11、R12Five yuan or hexatomic ring can be connected to form by N.
The compound of the present invention still further preferably are as follows: in logical formula (I)
R1、R2It is respectively selected from hydrogen, fluorine or chlorine；
R3、R4It is respectively selected from hydrogen；
R5Selected from hydrogen or methyl；
R6Selected from hydrogen, methyl or CH2OR10；
R7Selected from hydrogen, cyano, methyl, ethyl, CO2R9、CH2OR10Or CONR11R12；
R6、R7It is not simultaneously CO2R9Or CH2OR10；
R8Selected from hydrogen, methyl or ethyl；
R9Selected from hydrogen, methyl, ethyl, n-propyl, normal-butyl, isopropyl, tert-butyl, allyl, propargyl or methyl carbonyl Base oxygroup ethyl；
R10Selected from hydrogen, C1-C4Alkyl-carbonyl, C1-C4Halogenated alkyl carbonyl, C3-C6Naphthene base carbonyl, C1-C4Alkyl sulfonyl Base, C1-C4Halogenated alkyl sulfonyl, two (C1-C2) alkyl amino sulfonyl, two (C1-C3) alkyl amino-carbonyl, two (C1-C2) alkane Base aminothiocarbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl, phenyl C1-C2Alkyl-carbonyl, 2- methyl -4- chlorobenzene oxygen acetyl Base, 2,4 dichloro benzene oxygen acetyl group, thiophenecarbonyl groups are selected from such as flowering structure: R11Selected from hydrogen, C1-C4Alkyl or C1-C4Halogenated alkyl；
R12Selected from hydrogen, C1-C4Alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；
R11、R12It can be connected to form by N
The most preferred compound of the present invention are as follows: in logical formula (I)
R1、R2It is respectively selected from hydrogen, fluorine or chlorine；
R3、R4It is respectively selected from hydrogen；
R5Selected from hydrogen；
R6Selected from hydrogen；
R7Selected from hydrogen, cyano, methyl, ethyl, CO2R9、CH2OR10Or CONR11R12；
R8Selected from hydrogen, methyl or ethyl；
R9Selected from hydrogen, methyl, ethyl, n-propyl, normal-butyl, isopropyl, tert-butyl, allyl, propargyl or methyl carbonyl Base oxygroup ethyl；
R10Selected from hydrogen, C1-C4Alkyl-carbonyl, C1-C4Halogenated alkyl carbonyl, cyclopropane carbonyl, C1-C4Alkyl sulphonyl, C1- C4Halogenated alkyl sulfonyl, two (C1-C2) alkyl amino sulfonyl, two (C1-C3) alkyl amino-carbonyl, two (C1-C2) alkyl ammonia Base thiocarbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl, phenyl C1-C2Alkyl-carbonyl, 2- methyl -4- chlorobenzene oxygen acetyl group, 2, 4- Dichlorophenoxy acetyl group, thiophenecarbonyl groups are selected from such as flowering structure:
R11Selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, normal-butyl, tert-butyl, trifluoroethyl, bis-fluoro ethyls, 1- chlorine Ethyl, 1- chloropropyl or 2- chloropropyl；
R12Selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, normal-butyl, tert-butyl or C1-C4Alkoxy carbonyl C1-C4Alkane Base；
R11、R12It can be connected to form
In the definition of logical formula (I) compound given above, collects term used and is generally defined as follows:
Halogen: refer to fluorine, chlorine, bromine or iodine.Alkyl: linear or branched alkyl group, such as methyl, ethyl, propyl, isopropyl, just Butyl or tert-butyl.Naphthenic base: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopenta or cyclohexyl.Substituent group is such as Methyl, halogen etc..Halogenated alkyl: linear or branched alkyl group, the hydrogen atom on these alkyl can be partly or entirely by halogen atom It is replaced, for example, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl etc..Alkoxy: straight chain or Branched alkyl is keyed in structure through oxygen atom.Halogenated alkoxy: straight or branched alkoxyl, on these alkoxies Hydrogen atom can be partly or entirely replaced halogen atom.For example, chloromethane epoxide, dichloro methoxyl group, trichloromethoxy, fluorine methoxy Base, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, trifluoro ethoxy etc..Alkylthio group: linear or branched alkyl group, through sulphur original Sub-key is connected in structure.Halogenated alkylthio: linear chain or branched chain alkylthio group, the hydrogen atom on these alkyl can be part or all of Replaced halogen atom.For example, chloromethane sulfenyl, dichloro methyl mercapto, trichloro-methylthio, fluorine methyl mercapto, difluoro methyl mercapto, fluoroform Sulfenyl, chlorine fluorine methyl mercapto etc..Alkenyl: linear chain or branched chain alkenes, such as vinyl, 1- acrylic, 2- acrylic and different fourths Alkenyl, pentenyl and hexenyl isomers.Alkenyl further includes polyenoid class, such as 1,2- allene base and 2,4- hexadienyl.Alkyl Sulfonyl: linear or branched alkyl group is through sulfonyl (- SO2) be connected in structure, such as methyl sulphonyl.Halogenated alkyl sulfonyl: Linear or branched alkyl group sulfonyl, the hydrogen atom on alkyl can be partly or entirely replaced halogen atom.Alkyl sulphinyl: Linear or branched alkyl group is connected in structure through sulfonyl (- SO-), such as methylsulfinyl.Halogenated alkyl sulfonyl: straight chain or Branched alkyl sulfinyl, the hydrogen atom on alkyl can be partly or entirely replaced halogen atom.Alkoxy carbonyl: alkoxy It is connected in structure through carbonyl, such as CH3OCO- or CH3CH2OCO-.Alkoxyalkyl: alkyl-O- alkyl-, such as CH3OCH2-.Alkane Carbonyl oxygroup alkyl: alkyl-CO-O- alkyl-, such as CH3COOCH2、CH3COOCH2CH2Or C2H5COOCH2CH2Etc..Alkyl oxycarbonyl Base: alkyl is connected in structure through carbonyl, such as CH3CO- or CH3CH2CO- etc..Halogenated alkyl carbonyl: halogenated alkyl connects through carbonyl It is connected in structure, such as CF3CO- or CF2HCO- etc..Naphthene base carbonyl: naphthenic base is connected in structure through carbonyl, such as cyclopropyl formyl Base or cyclohexyl formoxyl etc..Halogenated cycloalkyl carbonyl: halogenated cycloalkyl is connected in structure through carbonyl, such as 1- chlorine cyclopropyl formyl Base etc..Alkyl amino sulfonyl: alkyl-NH-SO2, such as CH3NHSO2Or C2H5NHSO2Etc..Dialkyl amino sulfonyl: two Alkyl-N-SO2, such as (CH3)2NSO2Or (C2H5)2NSO2Etc..Alkyl amino-carbonyl: alkyl-NH-CO-, such as CH3NHCO- or C2H5NHCO- etc..Dialkyl amino carbonyl: dialkyl group-N-CO-, such as (CH3)2NCO- or (C2H5)2NCO- etc..Dialkyl amido Thiocarbonyl: dialkyl group-N-CS-, such as (CH3)2NCS- or (C2H5)2NCS- etc..Alkylthioalkylcarbonyl: alkyl-S-alkyl- CO, such as CH3SCH2CO or CH3SCH2CH2CO etc..Aryl: polynary aromatic group, such as phenyl, naphthalene.Heteroaryl is containing 1 or more The heteroatomic five-membered ring of a N, O, S or hexatomic ring.Such as furyl, pyrazolyl, thiazolyl, pyridyl group, pyrimidine radicals, pyrazinyl, Pyridazinyl, triazine radical, quinolyl etc..
Part of compounds of the invention can illustrate with the particular compound listed in table 1, but the present invention and not only limit In these compounds.
R in table3、R4=H
Table 1
Compound of Formula I of the present invention can usually be joined by amino-compound III and 3,4,5,6- tetrabydrophthalic anhydride II It flows back and obtains in acetic acid according to literature method, document such as US4846882, WO8707602 etc..
Work as R6Or R7Selected from CO2C2H5When (I-1, I-1 '), can refer to document description become carboxylic acid (I-2, I-2 ') then into One step formation ester type compound (I-3, I-3 ') and amides compound (I-4, I-4 '), document such as US20060223848, WO2012130798, WO2014048827, WO2014048940 etc..
Work as R6Or R7Selected from CH2OCOCH3When (I-5, I-5 '), it can refer to document description and obtained in methyl alcohol with excess acetyl chloride To alcohol compound (I-6, I-6 '), document such as synlett, 2005,10:1527-1530.Then with general formula R10The acyl that-X is represented Halogen, benzyl halogen or aromatic ring with labile halogen or hetero-aromatic ring react obtain I-7 or I-7 ' under alkaline condition.
React and carried out in suitable solvent, suitable solvent can be selected from benzene,toluene,xylene, acetone, tetrahydrofuran, Acetonitrile, N,N-dimethylformamide, N-Methyl pyrrolidone, methylene chloride, chloroform, dichloroethanes or ethyl acetate etc..Reaction It can be carried out in the presence of alkali or alkali-free, when being reacted in the presence of alkali, reaction can be accelerated to carry out.The alkali can To be selected from alkali metal hydride, such as sodium hydride, lithium hydride or Sodamide；Alkali metal hydroxide, such as sodium hydroxide or hydrogen-oxygen Change potassium；Alkali carbonate, such as sodium carbonate or potassium carbonate；Organic bases, such as pyridine, 4-dimethylaminopyridine, triethylamine, N- first Base pyrroles or diisopropyl ethyl amine etc..Reaction temperature can be in -10 DEG C of suitable solvent boiling point temperature selected into reaction Between, usually 0~100 DEG C.Reaction time is 30 minutes to 20 hours, usual 1~10 hour.
R10- X is commercially available.X is leaving group, and X is selected from chlorine, bromine or iodine.
Amino-compound III can conventionally be utilized iron, zinc, palladium carbon, stannous chloride etc. also by nitro compound IV Original reagent obtains, and specifically can refer to EP2044006；US20070155738；European Journal of Medicinal Chemistry,2013,65,32-40；Synlett,2010,(20),3019-3022；HETEROCYCLES,2008,75(1): 57-64 etc..Nitro compound IV can be described to synthesize through three steps by aldehyde VIII according to existing literature, document such as J.Agric.Food Chem.2005,53,8639-8643 or WO2006090234.
Outer except as otherwise indicating, each group definition is the same in reaction equation
The compound of the present invention can efficiently control the weeds such as barnyard grass, youth-and-old-age, herba setariae viridis, piemarker, under low dosage It is obtained with good effect.There is certain safety to wheat, corn, rice, agriculturally can be used as herbicide.Cause The invention also includes the purposes that logical formula (I) compound is used to control weeds for this.
The present invention also provides a kind of Herbicidal combinations, the composition is using logical formula (I) compound as active component, combination The weight percentage of active component in object is 0.1-99%.Therefore the invention also includes the compositions for controlling weeds Purposes.
Composition of the invention can prepare corresponding dosage form using method well known to those skilled in the art.Active group Divide the mixture that can contain single compound or several compounds of the invention.
Carrier system in the present composition meets the substance of following conditions: it is convenient for being applied to after preparing with active constituent Site to be processed, such as can be plant, seed or soil；Or be conducive to storage, transport or operation.Carrier can be solid Body or liquid are usually preparing carrier used in Herbicidal combinations including being usually gas but the substance for being compressed into liquid It can be used.
Suitable solid carrier includes the clay naturally synthesized and silicate (such as diatomite, talcum, Attagel, silicic acid Aluminium (kaolin), montmorillonite and mica；), calcium carbonate, calcium sulfate, ammonium sulfate, the silica of synthesis, synthetic calcium silicate, synthesis silicon Sour aluminium, natural resin, synthesis resin (the resin such as cumarone resin of natural resin, synthesis, polyvinyl chloride and benzene second Alkene polymer and copolymer), solid polystream phenol, pitch or wax (such as beeswax, paraffin).
Suitable liquid-carrier includes water；Alcohol (such as isopropanol and ethyl alcohol；Ketone such as acetone, methyl ethyl ketone, isopropyl methyl Ketone, cyclohexyl ketone), ether, aromatic hydrocarbons (such as benzene,toluene,xylene), petroleum distillate (such as kerosene and mineral oil), chlorohydrocarbon (such as tetrachloro Change carbon, perchloroethylene and trichloro ethylene) one or more of mixing.
Composition is usually processed into the form of concentrate and with this for transporting, by user that its is dilute before administration It releases.The presence of a small amount of supporting surfactant facilitates dilution.In this way, at least one in composition according to the invention Kind carrier is preferably surfactant.Such as composition can contain at least two carriers, wherein at least one is surfactant.
Surfactant can be emulsifier, dispersing agent or wetting agent；It is living that it can be non-ionic or ion surface Property agent.The example of suitable surfactant includes the sodium salt or calcium salt of polyacrylic acid and lignin sulfonic acid；Containing at least in molecule The fatty acid or fatty amine or amide and ethylene oxide of 12 carbon atoms and/or the condensation product of propylene oxide.Glycol, sorbierite, The condensation product of sucrose or pentaerythritol fatty ester and these esters and ethylene oxide and/or propylene oxide；Fatty alcohol or alkylbenzene Phenol such as p-Octylphenol or condensation product to octyl cresols and ethylene oxide and/or propylene oxide；The sulphur of these condensation products Hydrochlorate and sulfonate；At least alkali or alkaline earth metal salt of the sulfuric acid containing 10 carbon atoms or sulphonic acid ester in the molecule, it is excellent Select sodium salt, such as sulfuric acid laurate sodium, sulfuric acid secondary alkyl ester sodium, sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium, such as ten Dialkyl benzene sulfonic acids sodium salt.
The example of composition of the invention is wettable powder, pulvis, granule, aqua, emulsifiable concentrating agents, cream Agent, aerosol and smoke agent.The active constituent of the wettable powder usually weight containing 25-75%, and usually remove solid inert carrier Except, the also dispersing agent containing 3-10% weight, and the stabilizer and/or other additives of 0-10% weight if desired can be added Such as bleeding agent or sticker.Pulvis generally can be with composition similar with wettable powder but the not pulvis concentration of dispersing agent Agent is further diluted with solid carrier, obtains the composition of the usually active constituent of the weight containing 0.5-10%.Granula is usually made It is standby at having 10 to 100 mesh (1.676-0.152mm) size, and the preparation of agglomerating or injection technique can be used.Usual granula contains 0.5- The active constituent of 75% weight and additive (additive such as stabilizer, surfactant or the sustained release improvement of 0-10% weight Agent).Emulsifiable concentrating agents in addition to the solvents, usually contains cosolvent, 1-50%W/V active constituent, 2-20%W/V cream when needed Agent and the other additives of 0-20%W/V (additive such as stabilizer, bleeding agent or corrosion inhibitor).Suspension concentrating agents usually contains Have the active constituent of 10-75% weight, the dispersing agent of 0.5-15% weight, 0.1-10% weight other additive (additives Such as defoaming agent, corrosion inhibitor, stabilizer, bleeding agent and sticker).
Water dispersant and emulsion, such as the group obtained by the way that wettable powder or concentrate according to the invention is diluted with water Object is closed, the scope of the invention is also included in.Described emulsion can have two types of Water-In-Oil or oil-in-water.
It, can be than individually leading to formula (I) compound by the way that other one or more herbicides are added in the composition With broader spectrum of activity.In addition, other herbicides can mutual-through type (I) compound activity of weeding have synergistic effect, can also By logical formula (I) compound and other herbicide mixtures, the changes of contents range of effective component is very big in mixture, in mixture effectively at Divide content generally in 1%-95%, convenient content is in 5%-60%.
Advantage for present invention:
Using logical composition of the formula (I) compound as active component of the present invention, weeds can be effectively controlled, such chemical combination The weeds such as barnyard grass, piemarker, herba setariae viridis, youth-and-old-age can be effectively controlled as herbicide in object, and have one to wheat, corn, rice Fixed safety agriculturally can be used as herbicide.
Specific embodiment
Following specific embodiments are used to further illustrate the present invention, but the present invention is limited to absolutely not these examples.(except as otherwise note It is bright outer, raw materials used to be commercially available)
Synthetic example
The preparation of 1 compound 6 of embodiment
1) preparation of the fluoro- 5- nitrobenzoyl aldoxime of the chloro- 4- of 2-
The fluoro- 5- nitrobenzaldehyde of the chloro- 4- of 42g (0.206mol) 2- is dissolved in 200ml ethyl alcohol, is down to 0 DEG C, stirs lower drop The aqueous solution for adding 17.4g (0.25mol) hydroxylamine hydrochloride, is then warmed to room temperature and is stirred to react.After 2 hours, TLC monitoring has been reacted Entirely.It is poured into water, filters to obtain white solid 38.3g.103 DEG C of fusing point.
2) preparation of 3- (the fluoro- 5- nitrobenzophenone of the chloro- 4- of 2-) -5- methyl -4,5- dihydro-isoxazole -5- carboxylic acid, ethyl ester
The fluoro- 5- nitrobenzoyl aldoxime of the chloro- 4- of 43.7g (0.2mol) 2- is dissolved in 150ml n,N-Dimethylformamide, 30 DEG C are warming up to, 32g (0.24mol) NCS is added portionwise at such a temperature, pale yellow solution is formed, is maintained at 35 DEG C and reacts 1 Hour.It is down to room temperature, 300ml methylene chloride is added, then twice with the pickling of 1N salt, saturated common salt is washed twice, anhydrous slufuric acid Magnesium is dry, filters, and dichloromethane solution is down to 0-5 DEG C, 34.2g (0.3mol) methallyl acetoacetic ester and 31g is added dropwise The mixed liquor of (0.3mol) triethylamine is kept at this temperature reaction 1 hour.It is successively washed, is had with 1N hydrochloric acid and saturated common salt Machine is mutually dry with anhydrous magnesium sulfate, and precipitation rear pillar chromatographs (ethyl acetate: petroleum ether=1:3) and obtains light yellow solid 57g.Fusing point 73.5℃。
1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δ (ppm): 1.28 (t, 3H), 1.71 (s, 3H), 3.32 (d, 1H), 3.92 (d, 1H), 4.27 (q, 2H), 7.42 (d, 1H), 8.45 (d, 1H).
3) preparation of 3- (the fluoro- 5- aminophenyl of the chloro- 4- of 2-) -5- methyl -4,5- dihydro-isoxazole -5- carboxylic acid, ethyl ester
By 57g (0.18mol) 3- (the fluoro- 5- nitrobenzophenone of the chloro- 4- of 2-) -5- methyl -4,5- dihydro-isoxazole -5- carboxylic acid second Ester is dissolved in 300ml ethyl acetate, two hydrated stannous chloride of 163g (0.72mol) is added portionwise under heating, then under reflux Reaction 8 hours.TLC monitors fully reacting.It is cooled to room temperature, is added in ice water, adjusts pH to 8, ethyl acetate with sodium hydroxide Extraction, saturated common salt washing are evaporated under reduced pressure to 31g grease after anhydrous magnesium sulfate is dry, not purified to be directly used in next step Reaction.
4) preparation of compound 6
Successively by 10.3g (0.036mol) 3- (the fluoro- 5- aminophenyl of the chloro- 4- of 2-) -5- methyl -4,5- dihydro-isoxazole - 5- carboxylic acid, ethyl ester and 3,4,5,6- tetrahydro phthalate anhydride of 7.6g (0.05mol) are added in the reaction flask equipped with 100ml acetic acid, It is warming up to back flow reaction, forms dark solution, is kept at this temperature reaction 6 hours, solvent is divided exactly in decompression, and sodium bicarbonate is added Aqueous solution adjusts pH to 7, and ethyl acetate extraction, solvent rear pillar chromatography (ethyl acetate: stone is divided exactly in decompression after anhydrous magnesium sulfate is dry Oily ether=1:3) light yellow oil 8.56g.
1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):1.33(t,3H),1.71(s,3H),1.83(m, 4H),2.43(m,4H),3.41(d,1H),3.96(d,1H),4.27(m,2H),7.33(d,1H),7.63(d,1H)。
The preparation of 2 compound 5 of embodiment
Referring to the preparation of 1 compound 6 of example, the methallyl acetoacetic ester being added in (the 2nd) step is changed into methallyl Sour methyl esters.Grease.1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δ (ppm): 1.72 (s, 3H), 1.83 (m, 4H), 2.43 (m, 4H), 3.40 (d, 1H), 3.96 (s, 3H), 4.01 (d, 1H), 7.38 (d, 1H), 7.70 (d, 1H).
The preparation of 3 compound 4 of embodiment
8g (0.019mol) compound 6 is added in 20ml ethyl alcohol, it is water-soluble that 1.52g (0.038mol) sodium hydroxide is added Reaction 4 hours is stirred at room temperature in liquid.TLC monitors end of reaction, is poured into water, 1N salt acid for adjusting pH to 3, ethyl acetate extraction It takes, saturated common salt washing, anhydrous magnesium sulfate is dry, is evaporated under reduced pressure to 7.2g light yellow oil.
1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δ(ppm):1.69(s,3H),1.85(m,4H),2.44(m, 4H),3.41(d,1H),3.88(d,1H),7.35(d,1H),7.69(d,1H)。
The preparation of 4 compound 10 of embodiment
By 0.37g (0.89mmol) compound 4,0.11g (0.89mmol) bromo propane, 0.2g (1.45mmol) carbonic acid Potassium is added sequentially in the reaction flask equipped with 20ml acetonitrile, is warming up to back flow reaction, and TLC monitors fully reacting, mistake after 2 hours Filter, vacuum distillation rear pillar chromatography (ethyl acetate: petroleum ether=1:4) obtain light yellow liquid 0.21g.1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δ (ppm): 1.27 (m, 6H), 1.70 (s, 3H), 1.83 (m, 4H), 2.44 (m, 4H), 3.36 (m, 1H), 3.97 (d, 1H), 5.09 (m, 1H), 7.32 (d, 1H), 7.62 (d, 1H).
The preparation of 5 compound 27 of embodiment
1) 3- (the chloro- 5- of 2- (1,3- dioxy -1,3,4,5,6,7- hexahydro -2H- iso-indoles -2- base) -4- fluorophenyl) -5- first The preparation of base -4,5- dihydro-isoxazole -5- carboxylic acid chloride
7g (0.018mol) compound 4 is dissolved in 20ml methylene chloride, 6.9g (0.054mol) oxalyl chloride is added dropwise, in room The lower stirring of temperature 4 hours, TLC monitors end of reaction, and decompression divides exactly solvent, obtains 7.2g grease, it is not purified be directly used in it is next Step.
2) preparation of compound 27
Acyl chlorides made from 0.58g (1.4mmol) step 1 is dissolved in 10ml methylene chloride, 0.12g is carefully added into The mixed liquor of (2mmol) isopropylamine and 0.21g (2mmol) triethylamine, is kept at room temperature and is stirred to react 1h, TLC monitoring reaction Completely.Solvent is divided exactly in decompression, column chromatograph (ethyl acetate: petroleum ether=1:8) light yellow solid 0.18g, 211.6 DEG C of fusing point.1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δ (ppm): 0.85 (m, 4H), 1.69 (s, 3H), 1.83 (m, 4H), 2.44 (m, 4H), 3.36 (d, 1H), 3.81 (m, 1H), 3.93 (d, 1H), 7.09 (d, 1H), 8.59 (d, 1H), 9.45 (s, 1H).
The preparation of 6 compound 35 of embodiment
Referring to the preparation of 5 compound 27 of example, isopropylamine therein is changed into 4- piperidine methyl formate.Pale yellowish oil Object.1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δ (ppm): 0.78 (m, 4H), 1.70 (s, 3H), 2.06 (m, 4H), 2.11 (m, 1H), 2.62 (m, 4H), 3.26 (m, 1H), 3.48 (m, 4H), 4.49 (m, 1H), 7.32 (d, 1H), 8.68 (d, 1H).
The preparation of 7 compound 42,43 of embodiment
1) preparation of the fluoro- 5- nitrobenzoyl aldoxime of the chloro- 4- of 2- is according to 1 step 1 of embodiment.
2) preparation of (3- (the fluoro- 5- nitrobenzophenone of the chloro- 4- of 2-) -5- methyl -4,5- dihydro-isoxazole -5- base) methanol
The fluoro- 5- nitrobenzoyl aldoxime of the chloro- 4- of 56.8g (0.26mol) 2- is dissolved in 150ml n,N-Dimethylformamide, 30 DEG C are warming up to, 41.4g (0.31mol) NCS is added portionwise at such a temperature, pale yellow solution is formed, is maintained at 35 DEG C anti- It answers 1 hour.It is down to room temperature, 300ml methylene chloride is added, then twice with the pickling of 1N salt, saturated common salt is washed twice, anhydrous sulphur Sour magnesium is dry, filters, and dichloromethane solution is down to 0-5 DEG C, the pure and mild 34.4g of 24.5g (0.34mol) methylallyl is added dropwise The mixed liquor of (0.34mol) triethylamine is kept at this temperature reaction 1 hour.It is successively washed, is had with 1N hydrochloric acid and saturated common salt Machine is mutually dry with anhydrous magnesium sulfate, and precipitation rear pillar chromatographs (ethyl acetate: petroleum ether=1:3) and obtains light yellow solid 34g.Fusing point 117.1℃。
1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δ (ppm): 1.47 (s, 3H), 3.18 (d, 1H), 3.62 (s, 2H), 3.79 (d, 1H), 7.43 (d, 1H), 8.42 (d, 1H).
3) preparation of (3- (the fluoro- 5- aminophenyl of the chloro- 4- of 2-) -5- methyl -4,5- dihydro-isoxazole -5- base) methanol
By 40g (0.139mol) (3- (the fluoro- 5- nitrobenzophenone of the chloro- 4- of 2-) -5- methyl -4,5- dihydro-isoxazole -5- base) Methanol is dissolved in 200ml ethyl acetate, and two hydrated stannous chloride of 109.5g (0.49mol) is added portionwise under heating, is then being returned Flow down reaction 8 hours.TLC monitors fully reacting.It is cooled to room temperature, is added in ice water, adjusts pH to 8, acetic acid with sodium hydroxide Ethyl ester extraction, saturated common salt washing are evaporated under reduced pressure to 27g grease after anhydrous magnesium sulfate is dry, not purified to be directly used in down Single step reaction.
4) preparation of compound 43
Successively by 25.9g (0.1mol) (3- (the fluoro- 5- aminophenyl of the chloro- 4- of 2-) -5- methyl -4,5- dihydro-isoxazole -5- Base) methanol and 3,4,5,6- tetrahydro phthalate anhydride of 15.2g (0.1mol) be added in the reaction flask equipped with 200ml acetic acid, rise Temperature forms dark solution, is kept at this temperature reaction 6h, solvent is divided exactly in decompression, and it is water-soluble that sodium bicarbonate is added to back flow reaction Liquid adjusts pH to 7, and ethyl acetate extraction, solvent rear pillar chromatography (ethyl acetate: petroleum ether is divided exactly in decompression after anhydrous magnesium sulfate is dry =1:3) light yellow oil 27.8g.
1δ (ppm): 1.52 (s, 3H), 1.83 (m, 4H), 2.10 H-NMR (300MHz, internal standard TMS, solvent C DCl3) (s, 3H),2.44(m,4H),3.22(d,1H),3.45(d,1H),4.18(m,2H),7.33(d,1H),7.60(d,1H)。
5) preparation of compound 42
12g (0.03mol) compound 43 is added in the reaction flask equipped with 80ml methanol, 0.34g is added dropwise (0.0045mol) chloroacetic chloride, is stirred at room temperature reaction 8h, and TLC monitors fully reacting.Solvent is divided exactly in decompression, and dichloromethane is added Alkane is washed with saturated sodium bicarbonate, and organic phase is dry with anhydrous magnesium sulfate, vacuum distillation, column chromatography (ethyl acetate: petroleum ether= 1:4) white solid 9.86g, 130 DEG C of fusing point.
1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δppm 1.43(3H,s),1.83(4H,s),2.43(4H,s), 3.15(1H,d),3.58(1H,d),3.71(2H,m),7.32(1H,d),7.58(1H,d)。
The preparation of 8 compound 45 of embodiment
0.5g (1.4mmol) compound 42 and 0.15g (1.4mmol) cyclopropyl formyl chloride are added to equipped with 15ml toluene Reaction flask in, lower addition 0.3g (2.8mmol) triethylamine is stirred at room temperature, be then stirred at room temperature reaction 2 hours.TLC prison Fully reacting, vacuum distillation are surveyed, column chromatographs (ethyl acetate: petroleum ether=1:4) and obtains 0.5g light yellow oil.
1H-NMR (300MHz, internal standard TMS, solvent C DCl3)δppm 0.87-0.94(2H,m),0.98-1.06(2H,m), 1.52(3H,s),1.61-1.68(1H,m),1.83(4H,s),2.43(4H,s),3.25(1H,d),3.48(1H,d),4.13- 4.23(2H,dd),7.31(1H,t),7.61(1H,d)。
The preparation of 9 compound 320,321 of embodiment
Referring to the preparation of compound 42,43 in embodiment 10, wherein 2- will be substituted for by the fluoro- 5- nitrobenzaldehyde of the chloro- 4- of 2- Chloro- 5- nitrobenzaldehyde.
Compound 46,50,52,64,66,67,83,88,90,96,323,328,329,330,332,333,342,345, 351,365,368,374,396,399 synthesis can be obtained according to the preparation method of compound 45 in embodiment 8.
The synthesis of compound 282 can be obtained according to the preparation method of compound 4 in embodiment 3.
The synthesis of compound 284 can be obtained according to the preparation method of 1 compound 6 of example.
The synthesis of compound 286,290,291 can be obtained according to the preparation method of compound 10 in embodiment 4.
The physical property and nuclear magnetic data of part of compounds are shown in Table 2.
Table 2
Example of formulations
Active component folding hundred is post-dised in formula, and all percentage compositions are weight percentage.
10 35% missible oil of embodiment
Phosphorous acid is dissolved in cyclohexanone, compound 6 and ethoxylated triglycerides are added, is obtained transparent molten Liquid.
11 60% wettable powder of embodiment
Compound 43, dodecyl sodium naphthalene sulfonate, sodium lignin sulfonate and kaolin (being solid) are mixed, It is crushed in pulverizer, until particle reaches standard.
12 30% water slurry of embodiment
By compound 45 with answer 80% and dodecyl sodium naphthalene sulfonate of amount of water powder together in (1mm pearl) in the ball mill It is broken.Hemicellulose and propylene oxide are dissolved in remaining 20% water, and then said components are added in stirring.
13 40% suspending agent of embodiment
Compound 46 and other components are sufficiently mixed, thus obtained suspending agent, gained suspending agent, which is diluted with water, to be obtained To the dilution of any required concentration.
Biological activity determination
Herbicidal in embodiment Room 14
The activity of weeding test method of the compounds of this invention is as follows:
Quantitative gramineae weed (barnyard grass, Setaria glauca) and broadleaf weeds (youth-and-old-age, piemarker) seed are broadcast respectively In the dixie cup equipped with Nutrition Soil that diameter is 7cm, rear earthing 1cm is broadcast, is cultivated according to a conventional method after suppression, water drenching in greenhouse. Gramineae weed is long to 2~3 leaf phases, 2~4 leaf phase of broadleaf weeds cauline leaf spraying treatment；Soil spraying treatment is in after planting before seedling It carries out within 24 hours.By experimental design dosage, in (the Britain Engineer Research Ltd. design life of crawler type crops sprayer Produce) on carry out spraying treatment (atomisation pressure 1.95kg/cm2, spouting liquid 500L/hm2, crawler track speeds 1.48km/h).Test sets 3 Secondary repetition.Test material processing is placed on handling hall, after medical fluid dries in the shade naturally, is put in greenhouse and manages according to a conventional method, observes And record weeds to the response situation of medicament, preventive effect of the periodical visual inspection reagent agent to weeds after processing.
Preventive effect grade scale: 0 be it is invalid, weeds is are killed or serious inhibition by 100% completely.
By activity of weeding test discovery compound 4,5,6,10,27,35,42,43,45,46,50,52,64,66,67, 83、88、90、96、282、284、286、290、291、320、321、323、328、329、330、332、333、342、345、351、 365,368,374,396,399 in 1000g a.i./hm2Have before lower seedling, after seedling to youth-and-old-age, piemarker, herba setariae viridis and barnyard grass Have and roots out effect well.42,45,46,64,396 in 600g a.i./hm2It is high to youth-and-old-age and piemarker preventive effect before lower seedling In 90%.
Further active testing the results are shown in Table for 5 (all mass concentrations are as active ingredients).
5 part of compounds activity of weeding result of table
The measurement of 15 indoor security of embodiment
It is 9cm equipped with nutrition that quantitative crop (soybean, cotton, corn, wheat, rice) seed is sowed at diameter respectively In the dixie cup of soil, rear earthing 1cm is broadcast, is cultivated according to a conventional method after suppression, water drenching in greenhouse.3 leaf phase of gramineous crop, broad-leaved are made 2~4 leaf phase of object (1~2 trifoliolate leaf) carries out cauline leaf spraying treatment, before seedling soil spraying treatment in after planting 24 hours into Row.It is enterprising in crawler type crops sprayer (Britain Engineer Research Ltd. design production) by experimental design dosage Row spraying treatment (atomisation pressure 1.95kg/cm2, spouting liquid 500L/ha, crawler track speeds 1.48km/h).Test sets 3 repetitions. Test material processing is placed on handling hall, after medical fluid dries in the shade naturally, is put in greenhouse and manages according to a conventional method, observes and records confession Object is studied to the response situation of medicament, periodical visual inspection investigates safety of the reagent agent to crop after processing.Safety classification mark Quasi-: 0 indicates to crop without any damage, and 100 be to kill crop completely or seriously inhibit.
The 7.5-60g after seedling such as discovery compound 43,45,46,64,66,67,83,396 is measured by indoor security a.i./hm2There is preferable safety to wheat, corn and rice under dosage.

Claims (10)

1. a kind of tetrahydric phthalimide class compound containing isoxazoline, it is characterised in that: the tetrahydro containing isoxazoline Phthalimide derivatives structure is as shown in logical formula (I):
In formula:
R1、R2、R3、R4It is respectively selected from hydrogen, halogen, C1-C6Alkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group Or C1-C6Alkyl sulphonyl；
R5、R6It is respectively selected from hydrogen, cyano, C1-C6Alkyl, CO2R9、CH2OR10, phenyl or following group be independently selected from by 1-4 take The phenyl in generation: halogen, CN, NO2、C1-C8Alkyl, C1-C8Halogenated alkyl, C1-C8Alkoxy, C1-C8Halogenated alkoxy, C1-C8Alkane Epoxide carbonyl, C1-C8Alkylthio group or C1-C8Alkyl sulphonyl；
R7、R8It is respectively selected from hydrogen, cyano, C1-C6Alkyl, C1-C6Halogenated alkyl, CO2R9、CH2OR10、CH2NR11R12、CONR11R12、 Phenyl is independently selected from the phenyl that following group replaces: halogen, CN, NO by 1-42、C1-C4Alkyl, C1-C4Halogenated alkyl, C1- C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group or C1-C4Alkyl sulphonyl；
R9Selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C3-C6Alkenyl, C3-C6Alkynyl, C1-C6Alkoxy C1-C6Alkyl, C1- C6Alkyl carbonyl oxygroup C2-C6Alkyl, benzyl unsubstituted or that following group is independently selected from by 1-4: halogen, CN, NO2、C1-C8 Alkyl, C1-C8Halogenated alkyl, C1-C8Alkoxy, C1-C8Halogenated alkoxy, C1-C8Alkoxy carbonyl, C1-C8Alkylthio group or C1-C8 Alkyl sulphonyl；
R10Selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy carbonyl, C1-C6Alkyl-carbonyl, C1-C6Halogenated alkyl Carbonyl, C3-C6Naphthene base carbonyl, C3-C6Halogenated cycloalkyl carbonyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl, C1- C6Alkyl amino sulfonyl, two (C1-C6) alkyl amino sulfonyl, C1-C6Alkyl amino-carbonyl, two (C1-C6) alkyl amino carbonyl Base, two (C1-C6) thio-alkyl amino-carbonyl, C1-C6Alkylthio group C2-C6Alkyl-carbonyl, it is unsubstituted or be independently selected from by 1-4 Phenyl, the phenyl C of following group1-C2Alkyl, phenyl C2-C4Alkenyl, phenylcarbonyl group, phenyl C1-C2Alkyl-carbonyl, phenoxy group C1- C2Alkyl-carbonyl, phenyl C2-C4Alkenyl carbonyl, heteroaryl, heteroaryl C1-C2Alkyl, Heteroarylcarbonyl: halogen, CN, NO2、C1-C4 Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4 Alkyl sulphonyl or by 1-4 halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4Alkyl halide The phenoxy group that oxygroup independently replaces；
R11、R12It is respectively selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy carbonyl C1-C6Alkyl；And R11、R12It can To be connected to form five yuan or hexatomic ring by N.
2. compound described in accordance with the claim 1, it is characterised in that: in logical formula (I)
R1、R2、R3、R4It is respectively selected from hydrogen, halogen, C1-C6Alkyl or C1-C6Alkoxy；
R5Selected from hydrogen or C1-C6Alkyl；
R6Selected from hydrogen, C1-C6Alkyl, CO2R9Or CH2OR10；
R7Selected from hydrogen, cyano, C1-C6Alkyl, CO2R9、CH2OR10、CH2NR11R12Or CONR11R12；
R8Selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, phenyl are independently selected from the phenyl that following group replaces: halogen by 1-4 Element, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1- C4Alkylthio group or C1-C4Alkyl sulphonyl；
R9Selected from hydrogen, C1-C6Alkyl, C3-C4Alkenyl, C3-C4Alkynyl, C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkyl carbonyl oxygroup C2- C3Alkyl, it is unsubstituted or the benzyl that following group replaces: halogen, CN, NO is independently selected from by 1-42、C1-C6Alkyl or C1-C6 Halogenated alkyl；
R10Selected from hydrogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy carbonyl, C1-C6Alkyl-carbonyl, C1-C6Halogenated alkyl Carbonyl, C3-C6Naphthene base carbonyl, C3-C6Halogenated cycloalkyl carbonyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl, C1- C6Alkyl amino sulfonyl, two (C1-C6) alkyl amino sulfonyl, C1-C6Alkyl amino-carbonyl, two (C1-C6) alkyl amino carbonyl Base, two (C1-C6) thio-alkyl amino-carbonyl, C1-C6Alkylthio group C2-C6Alkyl-carbonyl, it is unsubstituted or be independently selected from by 1-4 The phenyl C that following group replaces1-C2Alkyl, phenylcarbonyl group, phenyl C1-C2Alkyl-carbonyl, phenyl C2-C4Alkenyl carbonyl, phenoxy group C1-C2Alkyl-carbonyl, thiophenecarbonyl groups, pyrazoles carbonyl, quinolinecarbonyl: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1- C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4Alkyl sulphonyl or by 1-4 halogen Element, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4The phenoxy group that halogenated alkoxy independently replaces；
R11、R12It is respectively selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；Alternatively, R11、 R12Five yuan or hexatomic ring can be connected to form by N.
3. compound according to claim 2, it is characterised in that: in logical formula (I)
R1、R2、R3、R4It is respectively selected from hydrogen, halogen or C1-C4Alkyl；
R5Selected from hydrogen or C1-C4Alkyl；
R6Selected from hydrogen, C1-C4Alkyl, CO2R9Or CH2OR10；
R7Selected from hydrogen, cyano, C1-C4Alkyl, CO2R9、CH2OR10、CH2NR11R12Or CONR11R12；
R8Selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl, phenyl are independently selected from the phenyl that following group replaces: halogen by 1-4 Element, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1- C4Alkylthio group or C1-C4Alkyl sulphonyl；
R9Selected from hydrogen, C1-C4Alkyl, C3-C4Alkenyl, C3-C4Alkynyl, C1-C4Alkoxy C1-C4Alkyl, C1-C4Alkyl carbonyl oxygroup C2- C4Alkyl, benzyl unsubstituted or that following group is independently selected from by 1-4: halogen, CN, NO2、C1-C4Alkyl or C1-C4It is halogenated Alkyl；
R10Selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl, C1-C4Halogenated alkyl Carbonyl, C3-C6Naphthene base carbonyl, C3-C6Halogenated cycloalkyl carbonyl, C1-C4Alkyl sulphonyl, C1-C4Halogenated alkyl sulfonyl, C1- C3Alkyl amino sulfonyl, two (C1-C3) alkyl amino sulfonyl, C1-C3Alkyl amino-carbonyl, two (C1-C3) alkyl amino carbonyl Base, two (C1-C3) thio-alkyl amino-carbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl, it is unsubstituted or be independently selected from by 1-4 The phenyl C of following group1-C2Alkyl, phenylcarbonyl group, phenyl C1-C2Alkyl-carbonyl, phenyl C2-C4Alkenyl carbonyl, phenoxy group C1-C2 Alkyl-carbonyl, thiophenecarbonyl groups, pyrazoles carbonyl or quinolinecarbonyl: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4 Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4Alkyl sulphonyl or by 1-4 halogen, CN、NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4The phenoxy group that halogenated alkoxy independently replaces；
R11、R12It is respectively selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；And R11、R12It can To be connected to form five yuan or hexatomic ring by N.
4. compound described in accordance with the claim 3, it is characterised in that: in logical formula (I)
R1、R2、R3、R4It is respectively selected from hydrogen, fluorine, chlorine or methyl；
R5Selected from hydrogen or methyl；
R6Selected from hydrogen, methyl, CO2R9Or CH2OR10；
R7Selected from hydrogen, cyano, methyl, ethyl, CO2R9、CH2OR10、CH2NR11R12Or CONR11R12；
R8Selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl, phenyl are independently selected from the phenyl that following group replaces: halogen by 1-4 Element, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4Halogenated alkoxy；
R9Selected from hydrogen, C1-C4Alkyl, allyl, propargyl, C1-C3Alkoxy C1-C3Alkyl, C1-C4Alkyl carbonyl oxygroup C2-C3Alkane Base, benzyl unsubstituted or that following group is independently selected from by 1-4: halogen, CN, NO2Or C1-C4Alkyl；
R10Selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl, C1-C4Halogenated alkyl Carbonyl, C3-C6Naphthene base carbonyl, C1-C4Alkyl sulphonyl, C1-C4Halogenated alkyl sulfonyl, two (C1-C2) alkyl sulfonyl amino Base, C1-C2Alkyl amino-carbonyl, two (C1-C3) alkyl amino-carbonyl, two (C1-C2) thio-alkyl amino-carbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl, phenylcarbonyl group, phenyl C unsubstituted or that following group is independently selected from by 1-41-C2Alkyl-carbonyl, benzene Oxygroup C1-C2Alkyl-carbonyl, thiophenecarbonyl groups, quinolinecarbonyl or pyrazoles carbonyl: halogen, CN, NO2、C1-C4Alkyl, C1-C4Alkyl halide Base, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4Alkyl sulphonyl or 2- Chloro-trifluoromethyl phenoxy；
R11、R12It is respectively selected from hydrogen, C1-C4Alkyl, C1-C4Halogenated alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；And R11、R12It can To be connected to form five yuan or hexatomic ring by N.
5. compound according to claim 4, it is characterised in that: in logical formula (I)
R1、R2It is respectively selected from hydrogen, fluorine, chlorine or methyl；
R3、R4It is respectively selected from hydrogen；
R5Selected from hydrogen or methyl；
R6Selected from hydrogen, methyl, CO2R9Or CH2OR10；
R7Selected from hydrogen, cyano, methyl, ethyl, CO2R9、CH2OR10Or CONR11R12；
R6、R7Selected from CO2R9Or CH2OR10, and R6With R7It is not identical；
R8Selected from hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, phenyl or the benzene that following group replaces is independently selected from by 1-4 Base: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy or C1-C4Halogenated alkoxy；
R9Selected from hydrogen, methyl, ethyl, n-propyl, normal-butyl, isopropyl, tert-butyl, allyl, propargyl, methoxy ethyl, second Oxygroup ethyl or methyl carbonyl oxygroup ethyl；
R10Selected from hydrogen, C1-C4Alkoxy carbonyl, C1-C4Alkyl-carbonyl, C1-C4Halogenated alkyl carbonyl, C3-C6Naphthene base carbonyl, C1- C4Alkyl sulphonyl, C1-C4Halogenated alkyl sulfonyl, two (C1-C2) alkyl amino sulfonyl, C1-C2Alkyl amino-carbonyl, two (C1-C3) alkyl amino-carbonyl, two (C1-C2) thio-alkyl amino-carbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl, it is unsubstituted or Person is independently selected from phenylcarbonyl group, the phenyl C of following group by 1-41-C2Alkyl-carbonyl, phenoxy group C1-C2Alkyl-carbonyl, quinoline Carbonyl or thiophenecarbonyl groups: halogen, CN, NO2、C1-C4Alkyl, C1-C4Halogenated alkyl, C1-C4Alkoxy, C1-C4Halogenated alkoxy, C1-C4Alkoxy carbonyl, C1-C4Alkylthio group, C1-C4Alkyl sulphonyl or 2- chloro-trifluoromethyl phenoxy；
R11Selected from hydrogen, C1-C4Alkyl or C1-C4Halogenated alkyl；
R12Selected from hydrogen, C1-C4Alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；
R11、R12Five yuan or hexatomic ring can be connected to form by N.
6. compound according to claim 5, it is characterised in that: in logical formula (I)
R1、R2It is respectively selected from hydrogen, fluorine or chlorine；
R3、R4It is respectively selected from hydrogen；
R5Selected from hydrogen or methyl；
R6Selected from hydrogen, methyl or CH2OR10；
R7Selected from hydrogen, cyano, methyl, ethyl, CO2R9、CH2OR10Or CONR11R12；
R6、R7Selected from CO2R9Or CH2OR10, and R6With R7It is not identical；
R8Selected from hydrogen, methyl or ethyl；
R9Selected from hydrogen, methyl, ethyl, n-propyl, normal-butyl, isopropyl, tert-butyl, allyl, propargyl or methyl carbonyl oxygroup Ethyl；
R10Selected from hydrogen, C1-C4Alkyl-carbonyl, C1-C4Halogenated alkyl carbonyl, C3-C6Naphthene base carbonyl, C1-C4Alkyl sulphonyl, C1- C4Halogenated alkyl sulfonyl, two (C1-C2) alkyl amino sulfonyl, two (C1-C3) alkyl amino-carbonyl, two (C1-C2) alkyl ammonia Base thiocarbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl, phenyl C1-C2Alkyl-carbonyl, 2- methyl -4- chlorobenzene oxygen acetyl group, 2, 4- Dichlorophenoxy acetyl group, thiophenecarbonyl groups are selected from such as flowering structure: R11Selected from hydrogen, C1-C4Alkyl or C1-C4Halogenated alkyl；
R12Selected from hydrogen, C1-C4Alkyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；
R11、R12It can be connected to form by N
7. compound according to claim 6, it is characterised in that: in logical formula (I)
R1、R2It is respectively selected from hydrogen, fluorine or chlorine；
R3、R4It is respectively selected from hydrogen；
R5Selected from hydrogen；
R6Selected from hydrogen；
R7Selected from hydrogen, cyano, methyl, ethyl, CO2R9、CH2OR10Or CONR11R12；
R8Selected from hydrogen, methyl or ethyl；
R9Selected from hydrogen, methyl, ethyl, n-propyl, normal-butyl, isopropyl, tert-butyl, allyl, propargyl or methyl carbonyl oxygroup Ethyl；
R10Selected from hydrogen, C1-C4Alkyl-carbonyl, C1-C4Halogenated alkyl carbonyl, cyclopropane carbonyl, C1-C4Alkyl sulphonyl, C1-C4Halogen Substituted alkyl sulfonyl, two (C1-C2) alkyl amino sulfonyl, two (C1-C3) alkyl amino-carbonyl, two (C1-C2) alkyl amino sulphur For carbonyl, C1-C2Alkylthio group C2-C4Alkyl-carbonyl, phenyl C1-C2Alkyl-carbonyl, 2- methyl -4- chlorobenzene oxygen acetyl group, 2,4- bis- Chlorobenzene oxygen acetyl group, thiophenecarbonyl groups are selected from such as flowering structure:
R11Selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, normal-butyl, tert-butyl, trifluoroethyl, bis-fluoro ethyls, 1- chloroethene Base, 1- chloropropyl or 2- chloropropyl；
R12Selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, normal-butyl, tert-butyl or C1-C4Alkoxy carbonyl C1-C4Alkyl；
R11、R12It can be connected to form
8. the application that a kind of logical formula (I) compound according to claim 1 is used for controlling weeds.
9. a kind of Herbicidal combinations, it is characterised in that: using logical formula (I) compound described in claim 1 as active component, group The weight percentage for closing the active component in object is 0.1-99%.
10. the application that a kind of Herbicidal combinations according to claim 9 are used for controlling weeds.
CN201410782605.0A 2014-12-16 2014-12-16 A kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline Active CN105777733B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410782605.0A CN105777733B (en) 2014-12-16 2014-12-16 A kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201410782605.0A CN105777733B (en) 2014-12-16 2014-12-16 A kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline

Publications (2)

Publication Number Publication Date
CN105777733A CN105777733A (en) 2016-07-20
CN105777733B true CN105777733B (en) 2018-12-14

Family

ID=56374077

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410782605.0A Active CN105777733B (en) 2014-12-16 2014-12-16 A kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline

Country Status (1)

Country Link
CN (1) CN105777733B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4092015A4 (en) * 2020-01-16 2024-03-06 Qingdao Kingagroot Chemical Compound Co Ltd Fused ring substituted aromatic compound and preparation method therefor, herbicidal composition, and use thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021082901A1 (en) * 2019-10-29 2021-05-06 沈阳中化农药化工研发有限公司 Phenylisoxazoline compound and use thereof
CN113880774B (en) * 2020-07-02 2023-12-08 沈阳中化农药化工研发有限公司 Preparation method of phenyl isoxazoline compound
CN115433177A (en) * 2021-06-03 2022-12-06 沈阳中化农药化工研发有限公司 Aryl isoxazoline compound and application thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1201113B (en) * 1986-01-10 1989-01-27 Fmc Corp HERBICIDE COMPOUNDS
US4892578A (en) * 1987-11-06 1990-01-09 Fmc Corporation Phenylmethyl-4,4-dimethyl-3-isoxazolidinone plant regulators
EP2186804B1 (en) * 2007-08-10 2015-06-17 Nippon Soda Co., Ltd. Nitrogen-containing heterocyclic compound and pest control agent

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4092015A4 (en) * 2020-01-16 2024-03-06 Qingdao Kingagroot Chemical Compound Co Ltd Fused ring substituted aromatic compound and preparation method therefor, herbicidal composition, and use thereof

Also Published As

Publication number Publication date
CN105777733A (en) 2016-07-20

Similar Documents

Publication Publication Date Title
CN105753853B (en) Isoxazoline-containing uracil compound and application thereof
KR101693375B1 (en) Halogen-substituted compounds used as pesticides
CN100427481C (en) An arylether kind compound and its preparation and application
JP4682315B2 (en) Substituted azole compounds and their production and use
JP4674672B2 (en) Benzopyrone compounds and their preparation and use
CN105566148B (en) A kind of quaternary ammonium compound and its application
CN111978225B (en) Trifluoroethyl sulfide (sulfoxide) substituted benzene compound and application thereof
JP4723642B2 (en) Substituted p-trifluoromethylphenyl ethers, their preparation and use
CN105777733B (en) A kind of tetrahydric phthalimide class compound and application thereof containing isoxazoline
CN103003240A (en) Substituted biaryl benzenesulfonamide compound and use
CZ2003493A3 (en) Disubstituted benzenes functioning as insecticidal agents
JP6895187B2 (en) New benzylamide compound, its production method, and acaricide
CN110054596B (en) Substituted oxadiazole compound and application thereof
WO2012065573A1 (en) Nitrogen heterocyclic substituted benzoyl compound and use thereof
CN104803929B (en) A kind of substituted oximinoether kind compound and application thereof
CN104803987B (en) Oxime-containing carboxylate compound and use thereof
CN113045561B (en) Diarylamine derivatives as fungicides
CN100410244C (en) Application of isoxazole compounds as bactericide
CN102395556A (en) Carboxylate compound and use thereof
CN105712925B (en) A kind of substituted sulfoamido (thio) carbonyls and application thereof
US4722749A (en) Pyridinesulfonamides and their use as herbicidal agents
CN105712926B (en) Substituted biaryl perfume base benzenesulfonamides and application thereof
CN108610283B (en) Secondary amine compound and preparation and application thereof
CN108976167B (en) Substituted phenylhydrazine compound and application thereof
CN106187866B (en) Pyridine acyl class compound and its preparation and application

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant