CN106187866A - Pyridine acyl compounds and preparation and application thereof - Google Patents

Pyridine acyl compounds and preparation and application thereof Download PDF

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CN106187866A
CN106187866A CN201610541173.3A CN201610541173A CN106187866A CN 106187866 A CN106187866 A CN 106187866A CN 201610541173 A CN201610541173 A CN 201610541173A CN 106187866 A CN106187866 A CN 106187866A
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alkyl
group
alkoxyl
halo
epoxide
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CN106187866B (en
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李为忠
白洪华
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Hefei Jinxiu Tianyuan Chemical Technology Co.,Ltd.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses a kind of pyridine acyl compounds or its stereoisomer, structure is as shown in formula I:

Description

Pyridine acyl compounds and preparation and application thereof
Technical field
The invention belongs to agricultural herbicide, insecticidal/acaricidal agent field.It is specifically related to a kind of pyridine acyl compounds and use On the way.Present invention additionally comprises compositions containing this compounds and application thereof and using method.
Background technology
Oryza sativa L. is one of topmost cereal crops in the world or even China.Whole world Monitoring of Paddy Rice Plant Area about 1.45 hundred million is public Hectare.China's rice growing area accounts for the 1/4 of whole nation cereal crops.Oryza sativa L. crop smothering area account for the 46% of the total cultivated area of Oryza sativa L. with On, Oryza sativa L. crop smothering major part is planted weeds by barnyard grass, Semen Euphorbiae, Herba Eleusines Indicae, Herba Cyperi Difformis etc. more than 10 and is caused, the most especially with barnyard grass The weeds such as grass, Herba Digitariae, Herba monochoriae vaginalis and dried tuber are maximum to rice hazard.Same Semen Maydis is also to plant widest crop in the world One of, cultivated area and total output are only second to Oryza sativa L., Semen Tritici aestivi, occupy the 3rd, from north latitude 58 ° (Canada and Russia) to south latitude 40 ° (South America) have plantation, have every month in the whole year Semen Maydis ripe in the world.Wherein, Semen Maydis is that the most important grain of the U.S. is made Thing, China produces Semen Maydis per year and accounts for second place of the world.World's Semen Maydis total output reached 10.09 hundred million tons in 2014.2008-2015 Year, world's Semen Maydis total output increases 1.74 hundred million tons, and rate of increase is 21.75%；Cultivated area, by 1.59 hundred million hectares, increases to 1.77 Hundred million hectares, increasing by 11.32%, Semen Maydis Weed infestation is wide and quite serious, and the weeds that main generation is bigger with hazard ratio have horse Tang, barnyard grass, Herba Setariae Viridis, Herba Eleusines Indicae, Amaranthus retroflexus, Herba Portulacae, Herba Acalyphae, Rhizoma Cyperi, field thistle etc..
Have a lot, such as about pyridine acyl compounds as the report of herbicide: EP316491, DE 3902818, EP 353187, JP 02078662, WO 2004058712, WO 2005058830, WO 2005058831 etc. are to this compounds Purposes as herbicide all has announcement.Wherein WO 2005058830 reports 5,6-substituted pyridine acyl compounds:
However, it is still necessary to continually develop new herbicides compounds, to meet the demand of agricultural production.
Summary of the invention
In order to meet the new demand agriculturally novel pesticide product constantly proposed, the invention provides a kind of novel structure Pyridine acyl compounds, this compounds as before herbicide Seedling, Miao Houjun can use, especially after Seedling use can be effective Prevent and kill off the most weeds of grass family, broad-leaved and Cyperaceae, and high to crop safety.There is good Insecticiding-miticiding simultaneously live Property.
Technical scheme is as follows:
The present invention provides a kind of pyridine acyl compounds, as shown in formula I:
In formula:
R1、R2、R3Selected from hydrogen, halogen, cyano group, nitro, C1-C6Alkyl, halo C1-C6Alkyl, C3-C6Cycloalkyl, C2-C6Chain Thiazolinyl, C2-C6Alkynyl group, C1-C6Alkoxyl, halo C1-C6Alkoxyl, C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, C1-C6 Alkylthio group, C1-C6Alkyl amino, C1-C6Alkyl sulphonyl, virtue that is unsubstituted or that be independently selected from the replacement of following group by 1-3 Base: halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alkoxyl, C1-C6Alkane sulfur Base or C1-C6Alkyl amino；
R4Selected from hydroxyl, C1-C6Alkoxyl, C1-C6Alkyl-carbonyl epoxide, C1-C6Alkylthio group, C1-C6Alkyl sulphonyl oxygen Base, C2-C6Alkenyloxy group, halo C2-C6Alkenyloxy group, C2-C6Alkynyloxy group, C1-C6Alkoxy carbonyl C1-C6Alkoxyl, C1-C6Alkylamino Carbonyl C1-C6Alkoxyl, unsubstituted or be independently selected from aryloxy group that following group replaces, arylthio, arylmethyl oxygen by 1-3 Base, aryl carbonyl epoxide, aryl sulfonyl epoxide, heteroaryl epoxide or aryl carbonyl methoxyl group: halogen, nitro, cyano group, C1-C6 Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl or halo C1-C6Alkoxyl；
R5Selected from C1-C3Alkyl, C3-C6Cycloalkyl, C1-C3Alkoxyl, C1-C3Alkoxy C1-C3Alkyl, C1-C3Alkyl oxycarbonyl Base, C1-C3Alkoxy carbonyl, C1-C3Alkylthio group or phenyl；
N=0-4；
Y is selected from C, N, O or S；
Z is selected from C, N, O, S, SO, SO2Or C=O；
When n >=2 and Z and/or Y are selected from C, it is positioned at two R on different C atom5CH can be connected into2；Or when n >= When 2, it is positioned at two R on same C or different C atom5Following group can be connected into: (CH2)2、(CH2)3、O、O(CH2)2O、O (CH2)3O、S(CH2)2S or S (CH2)3S；
Or its salt.
The present invention more preferably compound is: in formula I
R1、R2、R3Selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C3Alkyl, C3-C6Cycloalkyl, C2-C4Chain Thiazolinyl, C2-C4Alkynyl group, C1-C3Alkoxyl, halo C1-C3Alkoxyl, C1-C3Alkyl-carbonyl, C1-C3Alkoxy carbonyl, C1-C3 Alkylthio group, C1-C3Alkyl amino, C1-C3Alkyl sulphonyl, virtue that is unsubstituted or that be independently selected from the replacement of following group by 1-3 Base: halogen, nitro, cyano group, C1-C3Alkyl, halo C1-C3Alkyl, C1-C3Alkoxyl, halo C1-C3Alkoxyl, C1-C3Alkane sulfur Base or C1-C3Alkyl amino；
R4Selected from hydroxyl, C1-C3Alkoxyl, C1-C3Alkyl-carbonyl epoxide, C1-C3Alkylthio group, C1-C3Alkyl sulphonyl oxygen Base, C2-C4Alkenyloxy group, halo C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, C1-C3Alkoxy carbonyl C1-C3Alkoxyl, C1-C3Alkylamino Carbonyl C1-C3Alkoxyl, unsubstituted or by 1-3 be independently selected from phenoxy group that following group replaces, thiophenyl, benzyl epoxide, Benzoyloxy, benzenesulfonyl epoxide, pyridyloxy or benzoyl C1-C3Alkoxyl: fluorine, chlorine, bromine, nitro, cyano group, C1-C3 Alkyl, halo C1-C3Alkyl, C1-C3Alkoxyl or halo C1-C3Alkoxyl；
R5Selected from C1-C3Alkyl, C3-C6Cycloalkyl, C1-C3Alkoxyl, C1-C3Alkoxy C1-C3Alkyl, C1-C3Alkyl oxycarbonyl Base, C1-C3Alkoxy carbonyl, C1-C3Alkylthio group, phenyl；
N=0-4；
Y is selected from C, N, O or S；
Z is selected from C, N, O, S, SO, SO2Or C=O；
When n >=2, it is positioned at two R on different C atom5CH can be connected into2；Or when n >=2, it is positioned at same C or not With two R on C atom5Following group can be connected into: (CH2)2、(CH2)3、O、O(CH2)2O、O(CH2)3O、S(CH2)2S or S (CH2)3S；
Or its hydrochlorate, phosphate, formates, acetate, trifluoroacetic acid, oxalates, benzene sulfonate, citrate or Herba Marsileae Quadrifoliae Fruit acid salt.
Further preferred compound is: in formula I
R1、R2、R3Selected from hydrogen, halogen, cyano group, nitro, C1-C3Alkyl, halo C1-C3Alkyl, C3-C6Cycloalkyl, C2-C4Chain Thiazolinyl, C2-C4Alkynyl group, C1-C3Alkoxyl, halo C1-C3Alkoxyl, C1-C3Alkyl-carbonyl, unsubstituted or independent by 1-3 Selected from the substituted phenyl of following group, pyridine radicals, benzoyl, PYRIDYLCARBONYL, benzenesulfonyl, benzyl or picolyl: halogen Element, nitro, cyano group, C1-C3Alkyl, halo C1-C3Alkyl, C1-C3Alkoxyl, halo C1-C3Alkoxyl, C1-C3Alkylthio group or C1- C3Alkyl amino；
R4Selected from hydroxyl, C1-C3Alkoxyl, C1-C3Alkyl-carbonyl epoxide, C1-C3Alkyl sulphonyl epoxide, C2-C4Alkene oxygen Base, halo C2-C4Alkenyloxy group, unsubstituted or be independently selected from phenoxy group that following group replaces, benzyl epoxide, benzene first by 1-3 Acyloxy, benzenesulfonyl epoxide or benzoyl methoxyl group: fluorine, chlorine, bromine, nitro, cyano group, methyl, trifluoromethyl, methoxyl group or Trifluoromethoxy；
R5Selected from methyl, ethyl, cyclopropyl, methoxyl group, methoxy, methyl mercapto, phenyl；
N=0-2；
Y is selected from C, N；
Z is selected from C, N, O；
When n >=2, it is positioned at two R on different C atom5CH can be connected into2；Or when n >=2, it is positioned at same C or not With two R on C atom5Following group can be connected into: (CH2)2、(CH2)3、O、O(CH2)2O、O(CH2)3O、S(CH2)2S or S (CH2)3S；
Or its hydrochlorate, phosphate, formates, acetate, trifluoroacetic acid, oxalates, benzene sulfonate, citrate or Herba Marsileae Quadrifoliae Fruit acid salt.
Further preferably compound is: in formula I
R1、R2、R3Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, C1-C3Alkyl, halo C1-C3Alkyl, C1-C3Alcoxyl Base, halo C1-C3Alkoxyl, C1-C3Alkyl-carbonyl, unsubstituted or by 1-3 be independently selected from phenyl that following group replaces, Pyridine radicals, benzyl or picolyl: fluorine, chlorine, bromine, nitro, cyano group, C1-C3Alkyl, halo C1-C3Alkyl, C1-C3Alkoxyl, halogen For C1-C3Alkoxyl；
R4Selected from hydroxyl, methoxyl group, ethyoxyl, formyloxy, acetoxyl group, methyl sulphonyl epoxide, ethylsulfonyl Epoxide, pi-allyl epoxide, halogenated allyl epoxide, unsubstituted or by 1-3 be independently selected from phenoxy group that following group replaces, Benzyl epoxide, benzoyloxy, benzenesulfonyl epoxide or benzoyl methoxyl group: fluorine, chlorine, bromine, nitro, cyano group, methyl, trifluoro Methyl, methoxyl group or trifluoromethoxy；
N=0；
Y is selected from C；
Z is selected from C；
Or its hydrochlorate, phosphate, formates, acetate, trifluoroacetic acid, oxalates, benzene sulfonate.
Further preferably compound is: in formula I
R1、R2、R3Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, methyl, ethyl, formoxyl, acetyl group, trifluoro formyl Base, unsubstituted or be independently selected from, by 1-3, phenyl, the pyridine radicals that following group replaces: fluorine, chlorine, bromine, nitro, cyano group, first Base, trifluoromethyl, methoxyl group or trifluoromethoxy；
R4Selected from hydroxyl, methoxyl group, ethyoxyl；
N=0:
Y is selected from C；
Z is selected from C；
Or its hydrochlorate, phosphate, formates, acetate, trifluoroacetate, oxalates, benzene sulfonate.
Further preferably compound is: in formula I
R1、R2、R3Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, methyl, ethyl, unsubstituted or by 1-3 independent choosing From the substituted phenyl of following group, pyridine radicals: fluorine, chlorine, bromine, nitro, cyano group, methyl, trifluoromethyl, methoxyl group or trifluoro methoxy Base；
R4Selected from hydroxyl；
N=0；
Y is selected from C；
Z is selected from C；
Or its hydrochlorate, phosphate, formates, acetate.
In the definition of general formula compound given above, collect term used and be defined as follows:
Halogen (plain): refer to fluorine, chlorine, bromine or iodine.
Alkyl: straight or branched alkyl, such as methyl, ethyl, propyl group, isopropyl or the tert-butyl group.
Cycloalkyl: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopenta or cyclohexyl.Substituent group such as methyl, Halogen etc..
Haloalkyl: straight or branched alkyl, the hydrogen atom on these alkyl can partly or entirely be taken by halogen atom Generation.Such as, chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl or trifluoromethyl.
Alkyl sulphonyl: refer to straight or branched alkyl through sulfonyl (-SO2-) be connected in structure, such as sulfonyloxy methyl Base.
Alkoxyl: straight or branched alkyl is connected in structure through oxygen atom.
Halogenated alkoxy: straight or branched alkoxyl, the hydrogen atom on these alkoxyls can be partly or entirely by halogen Replaced.Such as, chloromethane epoxide, dichloromethane epoxide, trichloromethoxy, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine Fluorine methoxyl group, trifluoro ethoxy.
Alkylthio group: straight or branched alkyl is connected in structure through sulphur atom.
Halogenated alkylthio: straight or branched alkylthio group, the hydrogen atom on these alkylthio groups can be partly or entirely former by halogen Son is replaced.Such as, chloromethane sulfenyl, dichloromethane sulfenyl, trichloro-methylthio, fluorine methyl mercapto, difluoro methyl mercapto, trifluoromethylthio, Chlorine fluorine methyl mercapto.
Alkylamino: straight or branched alkyl is connected in structure through nitrogen-atoms.
Alkyl halide amino: straight or branched alkylamino, the hydrogen atom on these alkylaminos can be partly or entirely by halogen Replaced.
Thiazolinyl: straight or branched also can exist the unsaturated alkyl of double bond on any position, such as vinyl or allyl Base.
Alkynyl: straight or branched also can exist the unsaturated alkyl of three keys on any position, such as acetenyl or propargyl Base.
Aryl moiety in aryl and aryloxy group, aryl carbonyl and aryloxycarbonyl etc. includes phenyl or naphthyl etc..
Heteroaryl is containing the heteroatomic five-membered ring of one or more N, O, S or hexa-atomic aromatic ring.Such as pyridine radicals, furyl, phonetic Piperidinyl, pyrazinyl, pyridazinyl, triazine radical, quinolyl, pyrazolyl, thiazolyl etc..
In the compound of the present invention, (represent not with R and S respectively owing to configuration difference can form stereoisomer Same configuration), the present invention includes R type isomer and S type isomer and the mixture of any ratio thereof.
In the compound of the present invention, owing to tautomerism can exist multiple tautomer, the present invention includes owning Tautomer and the mixture of any ratio thereof.
In the logical formula (I) compound of the present invention, R1Moiety substituent be shown in Table 1.
Table 1
In the logical formula (I) compound of the present invention, R2、R3Moiety substituent with table 1.
Part of compounds in the present invention can illustrate by the particular compound listed in table 2, but these concrete chemical combination Thing does not limit the present invention.
Table 2
The compound of Formula I of the present invention can be prepared in accordance with the following methods:
Compound of Formula I can be by the compound shown in formula II and the replacement 2-pyridine carboxylic acid shown in general formula III or it is anti- Answering derivant (such as corresponding carboxylic acid halides, acyl cyanogen or ester), in the presence of dehydrant and one or more auxiliary agents, reaction prepares.
R in above-mentioned reaction equation1、R2、R3、R4As defined above with n.
Reaction carry out in suitable solvent, the optional oxolane freely of suitable solvent, dichloromethane, chloroform, acetonitrile, Toluene, dimethylbenzene, benzene, acetone or butanone etc..
The optional dicyclohexylcarbodiimide of suitable dehydrant (DCC), it is possible to selected from other reagent such as 1-(3-dimethylamino Propyl group)-3-ethyl carbodiimide (EDC) or N, N '-carbonyl dimidazoles (CDI) etc..
Suitable auxiliary agent is selected from such as Cyanogran., potassium cyanide .alpha.-hydroxyisobutyronitrile., cyano group trimethyl silane etc..
Reaction temperature can be between room temperature to solvent boiling point temperature, usually room temperature.
Response time is 30 minutes to 20 hours, usual 1～10 hour.
Raw material II, III are commercially available, and raw material II can also refer to the method in patent EP0283261, WO2005080344 certainly System.
Present invention additionally comprises the salt of compound of Formula I, including inorganic salt (example hydrochloric acid salt, phosphate, sodium salt, potassium salt etc.) and Organic salt (such as acetate, benzene sulfonate, oxalates etc.).Prepared above-mentioned salt by compound of Formula I and can use the skill of this area Method known to art personnel.
Bioactivity screening test shows that the compound of Formula I of the present invention has good activity of weeding.The change of the present invention Compound can be used for agriculturally preventing and kill off multiple weeds, and Miao Qian, Miao Houjun can use, and especially uses after Seedling and can effectively prevent and kill off standing grain originally The most weeds of section, broad-leaved and Cyperaceae.Meanwhile, the compound of Formula I of the present invention is to crop safety, such as to Oryza sativa L., jade Rice, Brassica campestris L, Semen Tritici aestivi have good safety.It addition, the logical formula (I) compound of the present invention is to agriculture, civilian and zoo technical In field, the adult of harmful insect, larva all demonstrate good pesticide and miticide actility.Therefore, present invention additionally comprises logical formula (I) Compound is used as the application of herbicide and/or insecticidal/acaricidal agent in agricultural and other field.
Present invention also offers a kind of weeding/insecticide acaricide composition, containing leading to as active component in said composition Compound of formula I, in compositions, the weight percentage of active component is 0.1-99%.Therefore present invention additionally comprises said composition to use In the purposes controlling weeds/insect evil demodicid mite.
The compositions of the present invention can use method well known to those skilled in the art to prepare.This compositions can contain The single compound of the present invention or the mixture of several compound.
Carrier system in the present composition meets the material of following condition: it is easy to be applied to after preparing with active component Pending site, such as, can be plant, seed or soil；Or be conducive to storing, transport or operating.Carrier can be solid Body or liquid, including usually gas but be compressed into the material of liquid, carrier generally used in preparation Herbicidal combinations All can use.
Suitably solid carrier includes the natural and clay of synthesis and silicate, such as kieselguhr, Talcum, Attagel, silicon Acid aluminum (Kaolin), montmorillonite and Muscovitum；Calcium carbonate；Calcium sulfate；Ammonium sulfate；The silicon oxide of synthesis and synthetic calcium silicate or silicic acid Aluminum；Element such as carbon and sulfur；Resin such as cumarone resin that is natural and that synthesize, polrvinyl chloride and styrene polymer and copolymerization Thing；Solid polystream phenol；Colophonium；Wax such as Cera Flava, paraffin.
Suitably liquid-carrier includes water；Alcohol such as isopropanol and ethanol；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；Vegetable oil；Vegetable oil is esterified Compound；Chlorohydrocarbon such as carbon tetrachloride, perchloroethylene and trichloro ethylene.Generally, the mixture of these liquid is also suitable.
Compositions is generally processed into the form of concentrate and with this for transporting, by user, it is dilute before administration Release.The existence of a small amount of supporting surfactant has and helps dilution.So, according in the compositions of the present invention at least one Plant carrier and be preferably surfactant.Such as compositions can contain at least two carrier, and at least one of which is surfactant.
Surfactant can be emulsifying agent, dispersant or wetting agent；It can be non-ionic or lives in the surface of ion Property agent.The suitably example of surfactant includes polyacrylic acid and the sodium salt of lignin sulfonic acid or calcium salt；Containing at least in molecule The fatty acid of 12 carbon atoms or fatty amine or amide and oxirane and/or the condensation substance of expoxy propane.Glycol, sorbitol, Sucrose or pentaerythritol fatty ester and these esters and oxirane and/or the condensation substance of expoxy propane；Fatty alcohol or alkylbenzene Phenol such as paraoctyl phenol or to octyl group cresols and oxirane and/or the condensation substance of expoxy propane；The sulfur of these condensation products Hydrochlorate and sulfonate；The most at least contain the sulphuric acid of 10 carbon atoms or the alkali metal of sulphonic acid ester or alkali salt, excellent Selecting sodium salt, such as sulphuric acid laurate sodium, sulphuric acid secondary Arrcostab sodium, sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium, such as ten Dialkyl benzene sulfonic acids sodium salt.
The example of the compositions of the present invention is wettable powder, powder, granule, water dispersible granules, water preparation, aqueous emulsion, water Suspending agent, cream, dispersible oil-suspending agent, emulsifiable powder (grain) agent, aerosol, aerosol and microemulsion.Wettable powder leads to The often wt. Active ingredient Han 25-75%, and generally in addition to solid inert carrier, possibly together with the dispersant of 3-10% weight, and If desired stabilizer and/or other additive such as penetrating agent or sticker of 0-10% weight can be added.Powder generally can be tool Formed by similar to wettable powder but be there is no the powder concentrating agents of dispersant, further dilute with solid carrier, obtain The generally compositions containing 0.5-10% weight activity component.Granule is generally prepared as having 10 to 100 mesh (1.676-0.152mm) Size, and prepared by available agglomerating or injection technique.The generally granule active component containing 0.5-75% weight and 0-10% weight adds Add agent such as stabilizer, surfactant, slow release modifying agent.Emulsifiable concentrating agents in addition to the solvents, usually contains the most molten when needed Agent, 1-50%W/V active component, 2-20%W/V emulsifying agent and other additive of 0-20%W/V such as stabilizer, penetrating agent and corruption Corrosion inhibitor.Suspension concentrating agents usually contains the active component of 10-75% weight, the dispersant of 0.5-15% weight, 0.1- Other additive of 10% weight such as defoamer, corrosion inhibitor, stabilizer, penetrating agent and sticker.
Water dispersant and Emulsion, the group such as obtained according to wettable powder or the concentrate of the present invention by dilute with water Compound, also lists the scope of the invention in.Described Emulsion can have Water-In-Oil or two types of oil-in-water.
By adding other one or more herbicide/insecticidal/acaricidal agents in the composition so that it is can individually lead to by ratio Compound of formula I has broader spectrum of activity.Additionally, other herbicide can the weeding/pesticide and miticide actility tool of mutual-through type I There is potentiation, it is possible to compound of Formula I is mixed with other herbicide/insecticidal/acaricidal agent, the content of effective ingredient in mixture Excursion is very big, and in mixture, active constituent content is typically at 1%-95%, and content conveniently is at 5%-60%.
Detailed description of the invention
Specific examples below is used for further illustrating the present invention, but the present invention is limited to absolutely not these examples.
Synthetic example
Example 1: the preparation of compound 2
1 is added, hydroresorcinol 0.22g (2mmol) in intermediate 3,6-dichloro-2-pyridyl formic acid 0.38g (2mmol) With 30ml acetonitrile, stirring is lower adds DCC 0.51g (2.5mmol), reacts 8h, be subsequently adding triethylamine 0.40g under room temperature (4mmol) He two .alpha.-hydroxyisobutyronitrile .s, continue to react under room temperature 3h, filter, filtrate decompression precipitation, residue adds 10ml water and 0.5g hydrochloric acid, ethyl acetate extracts 3 times, and aqueous phase sodium hydroxide is adjusted to neutrality, and ethyl acetate extracts, and organic facies is dried, precipitation, Obtain compound 2, off-white color solid 0.35g.
1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δ (ppm): 2.14 (m, 2H), 2.46 (t, 2H), 2.85 (t, 2H), 8.05 (d, 1H), 8.74 (d, 1H).
Example 2: the preparation of compound 227
1 is added, hydroresorcinol 0.22g (2mmol) in intermediate 4,6-bis-fluoro-2-pyridine carboxylic acid 0.32g (2mmol) With 30ml acetonitrile, stirring is lower adds DCC 0.51g (2.5mmol), reacts 8h, be subsequently adding triethylamine 0.40g under room temperature (4mmol) He two .alpha.-hydroxyisobutyronitrile .s, continue to react under room temperature 3h, filter, filtrate decompression precipitation, residue adds 10ml water and 0.5g hydrochloric acid, ethyl acetate extracts 3 times, and aqueous phase sodium hydroxide is adjusted to neutrality, and ethyl acetate extracts, and organic facies is dried, precipitation, Obtain compound 227, off-white color solid 0.30g.
1H-NMR (300MHz, internal standard TMS, solvent C DCl3) δ (ppm): 2.17 (m, 2H), 2.43 (t, 2H), 2.81 (t, 2H), 7.46 (dd, 1H), 8.08 (dd, 1H).
Other compounds of logical formula (I) can prepare by the preparation method that the present invention provides.
Part of compounds nuclear magnetic data (1HNMR, 300MHz, internal standard TMS, solvent C DCl3) as follows:
Compound 1, off-white color solid, δ (ppm): 2.16 (m, 2H), 2.48 (t, 2H), 2.87 (t, 2H), 7.86 (d, 1H), 8.43 (d, 1H).
Compound 3, off-white color solid, δ (ppm): 2.15 (m, 2H), and 2.47 (t, 2H), 2.85 (t, 2H), 8.30-8.43 (m, 2H).
Compound 7, off-white color solid, δ (ppm): 2.16 (m, 2H), 2.40 (s, 3H), 2.48 (t, 2H), 2.48 (s, 3H), 2.87 (t, 2H), 7.56 (d, 1H), 8.04 (d, 1H).
Compound 43, off-white color solid, δ (ppm): 2.10 (m, 2H), and 2.46 (t, 2H), 2.83 (t, 2H), 7.41-8.43 (m, 8H).
Compound 228, off-white color solid, 2.12 (m, 2H), 2.45 (t, 2H), 2.79 (t, 2H), 8.06 (dd, 1H), 8.54 (dd, 1H).
Example of formulations
In formula, active component is rolled over hundred post-dised, and all percentage compositions are weight percentage.
Example 3 30% aqueous suspension
By compound 1 with answer 80% and dodecyl sodium naphthalene sulfonate of amount of water in ball mill in (1mm pearl) together with powder Broken.Hemicellulose and expoxy propane are dissolved in remaining water of 20%, and then stirring adds said components.
Example 4 35% cream
Phosphorous acid is dissolved in cyclohexanone, is subsequently adding compound 2 and ethoxylated triglycerides, obtain transparent Solution.
Example 5 40% suspending agent
Compound 227 and other components being sufficiently mixed, thus obtained suspending agent, dilute with water gained suspending agent can obtain Diluent to any desired concn.
Example 6 60% wettable powder
Compound 228, dodecyl sodium naphthalene sulfonate, sodium lignin sulfonate and Kaolin (being solid) are blended in one Rise, pulverize in pulverizer, until granule reaches standard.
Biological activity determination
The indoor Herbicidal of example 7
Quantitative weed seed is sowed in the dixie cup equipped with Nutrition Soil of a diameter of 7cm respectively, broadcasts rear earthing 1cm, town In hot-house culture after pressure, trickle, thinning after emerging, field planting (grassy weed 10-20 strain/cup, broad leaved weed 2-4 strain/cup), treat The grassy weed 2-3 leaf phase, broad leaved weed length to 2-4 leaf period, by EXPERIMENTAL DESIGN dosage crawler type crops sprayer (Britain Engineer Research Ltd. designs production) carry out stem and leaf spraying treatment (atomisation pressure 1.95kg/cm2, spouting liquid 50ml/m2, crawler track speeds 1.48km/h).Test sets 3 repetitions.After medicinal liquid natural air drying, it is placed in greenhouse according to a conventional method Management, the growth promoter situation of routine observation examination material, and according to practical situation, periodical visual inspection investigation reagent agent pair after processing The preventive effect of weeds.Preventive effect grade scale: 0 is invalid, 100% for killing weeds completely or seriously suppressing.
Part of compounds and the comparison medicament work to Herba Digitariae, youth-and-old-age, Herba Abutili, Herba monochoriae vaginalis, Herba Setariae Viridis, Herba Acalyphae and barnyard grass Property data are shown in Table 3.
Table 3
The indoor Semen Maydis of example 8, Security of rice measure
Quantitative Semen Maydis, rice paddy seed are sowed in the dixie cup equipped with Nutrition Soil of a diameter of 7cm respectively, broadcast rear earthing 1cm, suppression, after trickle in hot-house culture, thinning after emerging, field planting (1-2 strain/cup), treat Semen Maydis, paddy growth to the 2-4 leaf phase, Stem and leaf spray is carried out by EXPERIMENTAL DESIGN dosage crawler type crops sprayer (Britain EngineerResearch Ltd. designs production) Mist processes (atomisation pressure 1.95kg/cm2, spouting liquid 50ml/m2, crawler track speeds 1.48km/h), test sets 3 repetitions.Treat medicinal liquid After natural air drying, managing according to a conventional method in being put in greenhouse, observe Semen Maydis, the growth promoter situation of Oryza sativa L., periodical visual inspection is investigated Reagent agent is to Semen Maydis, the safety of Oryza sativa L..Safety classification standard: 0 represents crop without any damage, and 100% for making Thing kills completely or seriously suppresses, and partial test the results are shown in Table 4.
Table 4
Example 9: insecticidal activity assay
With the compounds of this invention, several insecticides are carried out insecticidal activity assay test.Method for measuring is as follows:
After testing compound dissolves with the mixed solvent of acetone/methanol (1: 1), with the water containing 0.1% (wt) Tween 80 It is diluted to required concentration.
With diamondback moth as target, airbrush nebulization is used to carry out insecticidal activity assay.
Mensuration for diamondback moth: cabbage leaves card punch is broken into the leaf dish of diameter 1cm, airbrush spraying treatment Pressure be that 10psi (is roughly equal to 0.7kg/cm2), every leaf dish positive and negative is sprayed, and spouting liquid is 0.5ml.Access is often processed after drying in the shade 10 2 ages try worm, often process 3 times and repeat.Put into 25 DEG C, relative humidity 60～70% after process and observe indoor cultivation, 72 hours " Invest, Then Investigate " survival borer population, calculates mortality rate.
Partial test result is as follows:
When liquor strength is 1000mg/L, the compound that mythimna separata, aphid fatality rate reach 80% has 1,2,7,43,227.
Example 10: indoor acaricidal activity measures
If the one-tenth demodicid mite demodicid mite of Tetranychus cinnabarinus being carried out toxicity determination test with the compounds of this invention.Assay method is as follows:
Measure becoming demodicid mite toxicity: compound makes mother solution with acetone after weighing, and tells with containing 0.1% by EXPERIMENTAL DESIGN The standing tap water dilution series concentration of temperature 80.Take two panels true leaf Kidney bean Seedling, after inoculation Tetranychus cinnabarinus becomes demodicid mite and investigates radix, use Manual sprayer (DeVilbiss Atomizer M163) spraying treatment, often processes 3 times and repeats, process and be placed on standard sight Room, 72 hours " Invest, Then Investigate " survival demodicid mite numbers, calculate mortality rate.
If demodicid mite toxicity being measured: take two panels true leaf potted plant Kidney bean Seedling, then by female for health Tetranychus cinnabarinus one-tenth demodicid mite 10 Receiving on blade, remove into demodicid mite after 24 hours, ovum proceeds to cultivate, if spraying after entering demodicid mite phase investigation radix after 7-10 days Mist processes, and often processes 3 times and repeats, processes and be placed on standard sight room, 72 hours " Invest, Then Investigate " survival demodicid mite numbers, calculates mortality rate.
Partial test result is as follows:
When liquor strength is 1000mg/L, if the compound that Tetranychus cinnabarinus becomes demodicid mite, demodicid mite fatality rate reach 80% has 1,2, 7、43、227。

Claims (9)

1. pyridine acyl compounds or its stereoisomer, as shown in formula I:
In formula:
R1、R2、R3Selected from hydrogen, halogen, cyano group, nitro, C1-C6Alkyl, halo C1-C6Alkyl, C3-C6Cycloalkyl, C2-C6Alkene Base, C2-C6Alkynyl group, C1-C6Alkoxyl, halo C1-C6Alkoxyl, C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, C1-C6Alkane Sulfenyl, C1-C6Alkyl amino, C1-C6Alkyl sulphonyl, virtue that is unsubstituted or that be independently selected from the replacement of following group by 1-3 Base: halogen, nitro, cyano group, C1-C6Alkyl, halo C1-C6Alkyl, C1-C6Alkoxyl, halo C1-C6Alkoxyl, C1-C6Alkane sulfur Base or C1-C6Alkyl amino；
R4Selected from hydroxyl, C1-C6Alkoxyl, C1-C6Alkyl-carbonyl epoxide, C1-C6Alkylthio group, C1-C6Alkyl sulphonyl epoxide, C2- C6Alkenyloxy group, halo C2-C6Alkenyloxy group, C2-C6Alkynyloxy group, C1-C6Alkoxy carbonyl C1-C6Alkoxyl, C1-C6Alkyl amino-carbonyl C1-C6Alkoxyl, unsubstituted or be independently selected from aryloxy group that following group replaces, arylthio, arylmethyl epoxide, virtue by 1-3 Base carbonyl epoxide, aryl sulfonyl epoxide, heteroaryl epoxide or aryl carbonyl methoxyl group: halogen, nitro, cyano group, C1-C6Alkyl, Halo C1-C6Alkyl, C1-C6Alkoxyl or halo C1-C6Alkoxyl；
R5Selected from C1-C3Alkyl, C3-C6Cycloalkyl, C1-C3Alkoxyl, C1-C3Alkoxy C1-C3Alkyl, C1-C3Alkyl-carbonyl, C1- C3Alkoxy carbonyl, C1-C3Alkylthio group or phenyl；
N=0-4；
Y is selected from C, N, O or S；
Z is selected from C, N, O, S, SO, SO2Or C=O；
When n >=2 and Z and/or Y are selected from C, it is positioned at two R on different C atom5CH can be connected into2；Or when n >=2, It is positioned at two R on same C or different C atom5Following group can be connected into: (CH2)2、(CH2)3、O、O(CH2)2O、O(CH2)3O、S(CH2)2S or S (CH2)3S；
Or its salt.
Compound the most according to claim 1, it is characterised in that: in formula I
R1、R2、R3Selected from hydrogen, halogen, cyano group, nitro, C1-C4Alkyl, halo C1-C3Alkyl, C3-C6Cycloalkyl, C2-C4Alkene Base, C2-C4Alkynyl group, C1-C3Alkoxyl, halo C1-C3Alkoxyl, C1-C3Alkyl-carbonyl, C1-C3Alkoxy carbonyl, C1-C3Alkane Sulfenyl, C1-C3Alkyl amino, C1-C3Alkyl sulphonyl, virtue that is unsubstituted or that be independently selected from the replacement of following group by 1-3 Base: halogen, nitro, cyano group, C1-C3Alkyl, halo C1-C3Alkyl, C1-C3Alkoxyl, halo C1-C3Alkoxyl, C1-C3Alkane sulfur Base or C1-C3Alkyl amino；
R4Selected from hydroxyl, C1-C3Alkoxyl, C1-C3Alkyl-carbonyl epoxide, C1-C3Alkylthio group, C1-C3Alkyl sulphonyl epoxide, C2- C4Alkenyloxy group, halo C2-C4Alkenyloxy group, C2-C4Alkynyloxy group, C1-C3Alkoxy carbonyl C1-C3Alkoxyl, C1-C3Alkyl amino-carbonyl C1-C3Alkoxyl, unsubstituted or be independently selected from phenoxy group that following group replaces, thiophenyl, benzyl epoxide, benzene first by 1-3 Acyloxy, benzenesulfonyl epoxide, pyridyloxy or benzoyl C1-C3Alkoxyl: fluorine, chlorine, bromine, nitro, cyano group, C1-C3Alkane Base, halo C1-C3Alkyl, C1-C3Alkoxyl or halo C1-C3Alkoxyl；
R5Selected from C1-C3Alkyl, C3-C6Cycloalkyl, C1-C3Alkoxyl, C1-C3Alkoxy C1-C3Alkyl, C1-C3Alkyl-carbonyl, C1- C3Alkoxy carbonyl, C1-C3Alkylthio group, phenyl；
N=0-4；
Y is selected from C, N, O or S；
Z is selected from C, N, O, S, SO, SO2Or C=O；
When n >=2, it is positioned at two R on different C atom5CH can be connected into2；Or when n >=2, it is positioned at same C or different C Two R on atom5Following group can be connected into: (CH2)2、(CH2)3、O、O(CH2)2O、O(CH2)3O、S(CH2)2S or S (CH2)3S；
Or its hydrochlorate, phosphate, formates, acetate, trifluoroacetic acid, oxalates, benzene sulfonate, citrate or malic acid Salt.
Compound the most according to claim 2, it is characterised in that: in formula I
R1、R2、R3Selected from hydrogen, halogen, cyano group, nitro, C1-C3Alkyl, halo C1-C3Alkyl, C3-C6Cycloalkyl, C2-C4Alkene Base, C2-C4Alkynyl group, C1-C3Alkoxyl, halo C1-C3Alkoxyl, C1-C3Alkyl-carbonyl, unsubstituted or by 1-3 independent choosing From the substituted phenyl of following group, pyridine radicals, benzoyl, PYRIDYLCARBONYL, benzenesulfonyl, benzyl or picolyl: halogen, Nitro, cyano group, C1-C3Alkyl, halo C1-C3Alkyl, C1-C3Alkoxyl, halo C1-C3Alkoxyl, C1-C3Alkylthio group or C1-C3 Alkyl amino；
R4Selected from hydroxyl, C1-C3Alkoxyl, C1-C3Alkyl-carbonyl epoxide, C1-C3Alkyl sulphonyl epoxide, C2-C4Alkenyloxy group, halogen For C2-C4Alkenyloxy group, unsubstituted or be independently selected from phenoxy group that following group replaces, benzyl epoxide, benzoxy by 1-3 Base, benzenesulfonyl epoxide or benzoyl methoxyl group: fluorine, chlorine, bromine, nitro, cyano group, methyl, trifluoromethyl, methoxyl group or trifluoro Methoxyl group；
R5Selected from methyl, ethyl, cyclopropyl, methoxyl group, methoxy, methyl mercapto, phenyl；
N=0-2；
Y is selected from C, N；
Z is selected from C, N, O；
When n >=2, it is positioned at two R on different C atom5CH can be connected into2；Or when n >=2, it is positioned at same C or different C Two R on atom5Following group can be connected into: (CH2)2、(CH2)3、O、O(CH2)2O、O(CH2)3O、S(CH2)2S or S (CH2)3S；
Or its hydrochlorate, phosphate, formates, acetate, trifluoroacetic acid, oxalates, benzene sulfonate, citrate or malic acid Salt.
Compound the most according to claim 3, it is characterised in that: in formula I
R1、R2、R3Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, C1-C3Alkyl, halo C1-C3Alkyl, C1-C3Alkoxyl, halogen For C1-C3Alkoxyl, C1-C3Alkyl-carbonyl, unsubstituted or be independently selected from, by 1-3, phenyl, the pyridine that following group replaces Base, benzyl or picolyl: fluorine, chlorine, bromine, nitro, cyano group, C1-C3Alkyl, halo C1-C3Alkyl, C1-C3Alkoxyl, halo C1-C3Alkoxyl；
R4Selected from hydroxyl, methoxyl group, ethyoxyl, formyloxy, acetoxyl group, methyl sulphonyl epoxide, ethylsulfonyl epoxide, Pi-allyl epoxide, halogenated allyl epoxide, unsubstituted or be independently selected from, by 1-3, phenoxy group, the benzyl that following group replaces Epoxide, benzoyloxy, benzenesulfonyl epoxide or benzoyl methoxyl group: fluorine, chlorine, bromine, nitro, cyano group, methyl, fluoroform Base, methoxyl group or trifluoromethoxy；
N=0；
Y is selected from C；
Z is selected from C；
Or its hydrochlorate, phosphate, formates, acetate, trifluoroacetic acid, oxalates, benzene sulfonate.
Compound the most according to claim 4, it is characterised in that: in formula I
R1、R2、R3Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, methyl, ethyl, formoxyl, acetyl group, fluoroform acyl group, not Substituted or be independently selected from, by 1-3, phenyl, the pyridine radicals that following group replaces: fluorine, chlorine, bromine, nitro, cyano group, methyl, trifluoro Methyl, methoxyl group or trifluoromethoxy；
R4Selected from hydroxyl, methoxyl group, ethyoxyl；
N=0；
Y is selected from C；
Z is selected from C；
Or its hydrochlorate, phosphate, formates, acetate, trifluoroacetate, oxalates, benzene sulfonate.
Compound the most according to claim 5, it is characterised in that: in formula I
R1、R2、R3Selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano group, nitro, methyl, ethyl, unsubstituted or by 1-3 be independently selected from The lower substituted phenyl of group, pyridine radicals: fluorine, chlorine, bromine, nitro, cyano group, methyl, trifluoromethyl, methoxyl group or trifluoromethoxy；
R4Selected from hydroxyl；
N=0；
Y is selected from C；
Z is selected from C；
Or its hydrochlorate, phosphate, formates, acetate.
7. one kind according to the compound described in claim 1 for controlling the purposes of weeds.
8. the application according to the harmful demodicid mite of pest control in agricultural or other field of the compound described in claim 1.
9. a Herbicidal combinations, it is characterised in that: containing the compound of Formula I described in claim 1 as active component, group The weight percentage of the active component in compound is 0.1-99%.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1036202A (en) * 1988-02-01 1989-10-11 山道士有限公司 The improvement of organic compound or relevant organic compound
CN1039808A (en) * 1988-07-25 1990-02-21 希巴-盖吉股份公司 New herbicides
EP0428483A1 (en) * 1989-11-14 1991-05-22 Ciba-Geigy Ag Synergistic agent and method of selective weed control
CN1732166A (en) * 2002-12-30 2006-02-08 辛根塔参与股份公司 Novel herbicides
CN1906165A (en) * 2003-12-12 2007-01-31 辛根塔参与股份公司 New herbicides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1036202A (en) * 1988-02-01 1989-10-11 山道士有限公司 The improvement of organic compound or relevant organic compound
CN1039808A (en) * 1988-07-25 1990-02-21 希巴-盖吉股份公司 New herbicides
EP0428483A1 (en) * 1989-11-14 1991-05-22 Ciba-Geigy Ag Synergistic agent and method of selective weed control
CN1732166A (en) * 2002-12-30 2006-02-08 辛根塔参与股份公司 Novel herbicides
CN1906165A (en) * 2003-12-12 2007-01-31 辛根塔参与股份公司 New herbicides

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