CN106632258B - Tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound and its application - Google Patents
Tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound and its application Download PDFInfo
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- CN106632258B CN106632258B CN201611162218.2A CN201611162218A CN106632258B CN 106632258 B CN106632258 B CN 106632258B CN 201611162218 A CN201611162218 A CN 201611162218A CN 106632258 B CN106632258 B CN 106632258B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/42—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 condensed with carbocyclic rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
Abstract
The invention discloses tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound and its applications, and chemical structural formula is as shown in Formulas I or II:In formula, R1、R2、R3、R4Respectively hydrogen or C1~C3Alkyl or C1~C3Any one in halogenated alkyl；X is nitrogen or carbon；X1、X2、X3、X4、X5Any one respectively in hydrogen or fluorine or chlorine or bromine or iodine or trifluoromethyl or cyano or nitro.The invention further relates to the application of the composition containing above compound and tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone in terms of agricultural herbicide, some compounds have very high activity of weeding, good control efficiency can be obtained under 5 grams/acre of dosages.
Description
Technical field
The present invention relates to a kind of compounds, and in particular to a kind of tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl assimilation
Close object and its application.
Background technique
Fragrant phenoxy propionic acid (APP) analog derivative is as gramineae weed class herbicide, because having efficient, low toxicity, Gao Xuan
Selecting property and it is environmentally friendly the features such as, since listing, research be concerned.In such inhibited gramineae weed of herbicide
Acetyl-CoA carboxylase (ACCase), block plant body in ester fat acid synthesis, thus effective as selective prevent and kill off grass family
Weeds, thus on broad leaf crop without influence.
In general, the R configuration body of such compound is the active constituent of herbicide.In 1991, Novartis Co., Ltd developed
One is used for APP class herbicide --- the clodinafop-propargyl of wheat paddock, and hereafter, Dow Chemical and South Korea's chemical technology research institute are developed successively
Two kinds of APP class herbicide --- cyhalofop-butyl (P1) and metamifops (P2) for paddy field are gone out.The study found that working as benzene
After oxygroup is substituted by pyridine oxygroup, selectivity and activity will be greatly improved.In such APP class herbicide, the standing grain spirit of fluorine pyrrole second
It (P3) is representative herbicide.
To obtain the higher compound of activity, tetrahydroisoquinoline is introduced into fragrant phenoxy alkanoic acid structure by inventor, design
And synthesize it is a series of have no tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound reported in the literature, it is found that it has
Significant activity of weeding.
Summary of the invention
The present invention provides a kind of tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound and its isomers,
It is characterized in that, chemical structural formula is as shown in Formulas I or II:
In formula, R1、R2、R3、R4Respectively hydrogen or C1~C3Alkyl or C1~C3Any one in halogenated alkyl；X be nitrogen or
Carbon；X1、X2、X3、X4、X5Any one respectively in hydrogen or fluorine or chlorine or bromine or iodine or trifluoromethyl or cyano or nitro；
In the definition of compound (I or II) given above, no matter term used exclusive use is also used in compound word,
Represent following substituent group:
Alkyl: refer to linear or branched alkyl group；
Halogenated alkyl: referring to linear or branched alkyl group, hydrogen moiety on these alkyl or is all replaced by halogen atom；
The compound of the present invention can exist in the form of one or more isomers.Isomers includes enantiomter, non-
Enantiomter, geometric isomer.Such as formula (I, II) compound represented of the invention, due to connecting four on a carbon atom
Different substituent group and formed stereoisomer (respectively with R and S to indicate different configurations), the present invention includes R type isomers
With the mixture of S type isomers and their any ratios.
In preferred scheme, the specific structure of the tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound
Formula are as follows:
The invention further relates to the activity of weeding of the tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound,
There is significant activity of weeding under 5 grams/acre of dosages.
Formula (I or II) compound provided by the invention has good control of weeds effect, can under very low dosage
To obtain good effect.
Formula (I, II) compound provided by the invention, with bioactivity and part of compounds has biological well live
Property be especially agricultural, gardening, flowers and health weeds prevention and treatment in terms of show activity.Weeds described here include, but
It is not limited only to this:
Gramineae weed: herba digitariae, barnyard grass, herba setariae viridis, hard grass, Wang grass, herba bromi japonici, amur foxtail, Triticum tauschii, alkali thatch, stinkgrass flower,
Wild avena sativa, rye grass；
Broadleaf weeds: piemarker, herba stellariae mediae, black nightshade, Chenopodiaceae, concave head amaranth, Amaranthus retroflexus etc..
It is effectively that they can also be with other to control weeds when formula of the invention (I or II) compound is used alone
Biochemical is used together, these biochemicals include other herbicides.
The invention further relates in the tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound agricultural herbicide
Application.
The synthesis material of tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound of the present invention is easy to get, system
Preparation Method is simple, easy to industrialized production.
Specific embodiment
Below with reference to specific implementation, the present invention is furture elucidated.These embodiments are interpreted as being merely to illustrate the present invention
Rather than for limiting the scope of the invention.After having read the content of the invention recorded, those skilled in the art can
To make various changes or modifications to the present invention, these equivalence changes and modification are equally fallen into defined by claims of the present invention
Range.
Embodiment 1:(R)-tetrahydroisoquinoline -2- base -2- [4- (5- chloro-3-fluoropyridine -2- oxygroup) phenoxy group] acetone (1)
Preparation
N,N-Dimethylformamide (40mL), (R) -2- (4- hydroxy benzenes oxygen) propionic acid (0.02mol, 3.64g), potassium carbonate
(0.02mol, 2.76g) adds the potassium carbonate of equivalent after stirring 0.5h at 75 DEG C, continues to stir 0.5h.2,3- is slowly added dropwise
Difluoro-5-chloropyridine (0.02mol, 3.00g), after being added dropwise, reaction temperature maintains 75 DEG C, 12h.Stop heating, is cooled to
Room temperature pours into reaction solution in 100mL ice water, and dilute hydrochloric acid adjusts pH 4-5, and filtering is washed three times with a small amount of ice water, and vacuum is dry
It is dry, obtain (R) -2- [4- (the fluoro- 5- chloropyridine -2- oxygroup of 3-) phenoxy group] propionic acid white solid 3.86g, yield 62.0%.
Toluene 40mL, (R) -2- [4- (the fluoro- 5- chloropyridine -2- oxygroup of 3-) phenoxy group] propionic acid (3.3mmol, 1.04g), adds
Enter into the single-necked flask of 100mL, after stirring and dissolving, is added thionyl chloride (20mmol, 2.24g), back flow reaction 4h, decompression is steamed
It evaporates, obtains (R) -2- [4- (the fluoro- 5- chloropyridine -2- oxygroup of 3-) phenoxy group] propionyl chloride yellow oily liquid, without isolating and purifying,
It is directly used in and reacts in next step.
Dichloromethane is added into above-mentioned (R) -2- [4- (the fluoro- 5- chloropyridine -2- oxygroup of 3-) phenoxy group] propionyl chloride reaction flask
Alkane (40mL), tetrahydroisoquinoline (0.44g, 3.30mmol), 4-dimethylaminopyridine (0.02g, 0.17mmol) stir under ice bath
15min.Triethylamine (1.37mL, 10mmol) is added dropwise, after being added dropwise, continues stirring 10 minutes, then removes ice bath, allow
It returns naturally and is warmed to room temperature, and stops reaction after stirring 4h, reaction solution is poured into 150mL ice water, methylene chloride extracts (40mL*
3), combining extraction liquid is successively washed twice with 50mL saturated sodium bicarbonate solution, and 100mL is washed three times, the anhydrous sulphur of gained organic phase
Sour sodium is dry, removes methylene chloride, silica gel column chromatography separating purification product, eluant, eluent (V under reduced pressurePetroleum ether: VEthyl acetate=3:1), it obtains
(R)-tetrahydroisoquinoline -2- base -2- [4- (5- chloro-3-fluoropyridine -2- oxygroup) phenoxy group] acetone (1) yellow oily liquid
0.22g, yield 15.6%；1H NMR(CDCl3, 400MHz) and δ: 1.67 (d, J=6.8Hz, 3H, CHCH3 ), 2.73~2.94 (m,
2H,NCH2CH 2), Ph 3.64~3.99 (m, 2H, NCH 2CH2), Ph 4.66~4.96 (m, 2H, NCH 2), Ph 5.01 (q, J=
6.8Hz,1H,CHCH3), 6.91~7.20 (m, 8H, PhH), 7.48 (dd, J=8.8Hz, 2.0Hz, 1H, Py-H), 7.85 (d, J
=2.0Hz, 1H, Py-H)；13C NMR(CDCl3,100MHz)δ:17.87,29.52,44.98,46.82,74.91,115.77,
122.39,124.82,125.00,126.51,128.38,128.96,132.72,133.73,140.13,145.63,146.93,
148.27,151.19,154.61,170.03.
Embodiment 2:(R)-tetrahydroisoquinoline -2- base -2- [4- (3- chloro-5-trifluoromethylpyridine -2- oxygroup) phenoxy group]
The preparation of acetone (2)
(R) -2- (4- hydroxyphenoxy) propionic acid (3.00g), DMF (35ml) are slowly added to K2CO3(4.55g), is warming up to
70~80 DEG C, 1h is stirred, 2,3-, bis- chloro-5-trifluoromethylpyridine (3.56g) is added dropwise, 70~80 DEG C of stirring 8h is kept, stops
It only reacts, cooled to room temperature, pours the mixture into ice water (100mL), adjust pH 4~5 using dilute hydrochloric acid, use acetic acid
Ethyl ester extraction, organic phase washing, dry, precipitation obtains (R) -2- [4- (5- trifluoromethyl -3- chloropyridine -2- oxygroup) phenoxy group] third
Sour brown liquid 5.03g, yield 84.4%.
(R) -2- [4- (5- trifluoromethyl -3- chloropyridine -2- oxygroup) phenoxy group] propionic acid (3.3mmol, 1.08g), is dissolved in
In toluene (35mL), SOCl is added dropwise2(20mmol, 2.24g), is heated to reflux, and reacts 4h, and precipitation obtains (R) -2- [4- (5- fluoroform
Base -3- chloropyridine -2- oxygroup) phenoxy group] propionyl chloride be directly used in next step.
Gained acyl chlorides is dissolved in methylene chloride (35mL), and 1,2,3,4- tetrahydroisoquinoline (0.44g) of intermediate is added and urges
The DMAP of change amount is slowly dropped into triethylamine (1.37mL, 10mmol) with stirring, is stirred to react 5h.Reaction is completed, by mixture
It to pouring into ice water (100mL), is extracted with methylene chloride (80mL*2), organic phase washing, dry, precipitation.It is chromatographed through column pure
Change to obtain white solid (R)-tetrahydroisoquinoline -2- base -2- [4- (3- chloro-5-trifluoromethylpyridine -2- oxygroup) phenoxy group] acetone
(2) 0.66g, m.p.47~48 DEG C, yield 41.90%.1H NMR: δ 1.67 (d, J=6.8Hz, 3H, CHCH3 ),2.73-2.94
(m,2H,CH2CH2 ),3.64-4.01(m,2H,CH2),4.66-4.97(m,2H,CH2), 5.03 (q, J=6.8Hz, 1H,
CHCH3),6.94-7.21(m,8H,Ph-H),7.96(s,1H,Py-H),8.24(s,1H,Py-H)；13C NMR:δ17.89,
29.56,45.02,46.86,75.07,115.85,115.96,119.18,122.64,122.76,126.39,126.55,
126.66,127.04,128.39,132.75,136.19,142.53,146.80,155.01,161.32,170.00.
Embodiment 3:(R)-tetrahydroisoquinoline -2- base -2- [4- (4 cyano -2- fluorophenoxy) phenoxy group] acetone (3) system
It is standby
In n,N-Dimethylformamide (DMF, 40mL), addition (R) -2- (4- hydroxy benzenes oxygen) propionic acid (3.03g,
0.02mol), potassium carbonate (5.52g, 0.04mol) is added portionwise, is warming up at 70 DEG C~80 DEG C, persistently stirs 1h, is added by amount
(2.38g, the 0.02mol) of 3,4- difluorobenzonilyiles, continues to be stirred to react 6~7h.It is cooled to room temperature, pours into ice water (250mL),
Be slowly added to dilute hydrochloric acid, be adjusted to pH 4~5, filter, washing, vacuum dried case it is dry (R) -2- [4- (4- cyano -2-
Fluorophenoxy) phenoxy group] propionic acid gray solid (R) -2- [4- (4- cyano -2- fluorophenoxy) phenoxy group] propionic acid 3.26g, produce
Rate 65.7%.
(R) -2- [4- (4- cyano -2- fluorophenoxy) phenoxy group] propionic acid (1.00g, 3.3mmol) is dissolved in toluene
In (40ml), it is slowly added to SOCl2(1.18g, 10mmol), back flow reaction 5h after sloughing solvent with Rotary Evaporators, obtain (R)-
2- [4- (4- cyano -2- fluorophenoxy) phenoxy group] propionyl chloride, directly progress next step reaction.
Gained acyl chlorides is dissolved in methylene chloride (40ml), 1,2,3,4- tetrahydroisoquinolines (0.44g, 3.3mmol) are added
With the 4-dimethylaminopyridine (DMAP) of catalytic amount, 10min is stirred under ice bath, and triethylamine (1g, 10mmol) is added dropwise dropwise.After
Continuous stirring 3h to 10h.After the reaction was completed, it pours into 100ml ice water, is extracted with dichloromethane, collect organic phase, and be washed with water
(100ml × 2), gained crude product is dry with anhydrous sodium sulfate, after precipitation through silica gel chromatographic column purify yellow mucus (R)-
Tetrahydroisoquinoline -2- base -2- [4- (4 cyano -2- fluorophenoxy) phenoxy group] acetone (3) 1.08g, yield 78.9%.1H NMR:
δ 1.68 (d, J=6.8Hz, 3H, CHCH 3), 2.75~2.90 (m, 2H, Ph-CH 2), 3.78~4.02 (m, 2H, N-CH2),4.68
~4.89 (m, 2H, Ph-CH2- N), 5.05 (q, J=6.8Hz, 1H, CHCH3), 6.74~6.85 (m, 1H, PhH), 6.88~
7.00 (m, 4H, PhH), 7.07~7.23 (m, 4H, PhH), 7.29~7.33 (m, 1H, PhH), 7.44 (dd, J=10.0Hz,
2.0Hz,1H,PhH)；13C NMR:δ17.98,29.56,45.02,46.88,75.00,106.09,116.47,118.63,
120.46,120.67,121.17,125.93,126.68,127.06,128.39,128.98,129.32,132.73,148.58,
150.47,153.63,154.80,169.93.
Embodiment 4:(R)-tetrahydroisoquinoline -2- base -2- [4- (the chloro- quinoxaline -2- oxygroup of 6-) phenoxy group] acetone (4)
Preparation
N,N-Dimethylformamide (DMF) (40mL) is added in 100mL reaction flask, by (R) -2- (4- hydroxy benzenes oxygen) third
Sour (3.0g, 0.02mol) is added in reaction flask, stirring and dissolving.At room temperature, be slowly added in batches potassium carbonate (4.46g,
0.033mol), continue 15~30min of stirring, be warming up to 75 DEG C of stirring 2h, be slowly added to 2,6- dichloro-quinoxaline (3.28g,
0.02mol), 145 DEG C of reaction 6h are warming up to.After reaction, it is cooled to room temperature, reaction solution is poured into ice water (250mL), drip
Add dilute hydrochloric acid to pH=4~5, filters, washing is dried to obtain solid (R) -2- (4- ((6- chloro-quinoxaline -2- base) oxygen) of yellow
Benzene oxygen) propionic acid 5.55g, yield 97%.
Toluene (40mL) is added in 100mL reaction flask, (R) -2- (4- ((6- chloro-quinoxaline -2- base) oxygen) benzene oxygen) propionic acid
(1.0g, 3.3mmol) is added with stirring thionyl chloride (1.19g, 10mmol), is warming up to 125 DEG C, back flow reaction 4h, cooling is de-
It is molten to obtain (R) -2- (4- ((6- chloro-quinoxaline -2- base) oxygen) benzene oxygen) propionic acid acyl chlorides, it is directly used in next step.
Methylene chloride (40mL) is added in the reaction flask equipped with acyl chlorides, 1,2,3,4- tetrahydroisoquinoline (0.44g,
3.3mmol) and DMAP (catalytic amount), triethylamine (1.0g, 10mmol) is instilled under ice bath stirring.After reaction mixture is stirred 7h
It pours into 200mL ice water, methylene chloride extraction.Organic phase is washed, anhydrous sodium sulfate drying is added, sloughs solvent and is slightly produced
Object.Column chromatographs (VPetroleum ether/ethyl acetate=2:1) obtain 0.50g faint yellow solid (R)-tetrahydroisoquinoline -2- base -2- [4- (chloro- quinoline of 6-
Quinoline -2- oxygroup) phenoxy group] acetone (4), yield 33.06%, m.p.48-50 DEG C,1H NMR: δ 1.69 (d, J=6.8Hz,
3H,CHCH 3), 2.74~2.95 (m, 2H, CH 2), 3.95~4.04 (m, 2H, N-CH 2), 4.70~4.98 (m, 2H, Ph-CH2-
), N 5.06 (q, J=6.8Hz, 1H, CHCH3), 6.95~7.00 (m, 2H, PhH), 7.10~7.21 (m, 6H, Ph-H), 7.56
~7.69 (m, 2H, quinoxaline-H), 8.04 (d, J=2.4Hz, 1H, quinoxaline-H), 8.65 (s, 1H,
quinoxaline-H)；13C NMR:δ17.94,29.57,45.01,46.87,74.96,115.77,115.89,122.43,
122.60,125.92,126.54,126.68,127.93,128.38,128.79,131.10,132.83,138.51,139.76,
(140.09,146.55,154.83,157.19,170.06.HRMS ESI, posotive mode): 460.1412 (M+H+)。
Embodiment 5: activity of weeding evaluation
Method is as follows: (1) in sectional area 64cm2Plastic tub alms bowl in quantitatively to fill soil pressure flat, be placed in Stainless steel basin, choose
Full seed, seed of the same size divide monocotyledon weed (herba digitariae Digitaria sanguinalis, barnyard grass
Echinochloa crus-galli, herba setariae viridis Setaria viridis) and broadleaf weed (piemarker Abutilon
It is theophrasti (or herba stellariae mediae Stelleria media or black nightshade Solanum nigrum), Chenopodiaceae Chenopodium album, recessed
Head amaranth Amaranthus ascedense or Amaranthus retroflexus Amaranthus retroflexus) divide alms bowl to sow, respectively account for alms bowl area
1/3,1cm thickness fine earth is covered, upper layer of soil infiltration is added water to from plastic tub alms bowl bottom, is placed in hot-house culture, it is long to required to test material
Leaf age carries out test process；(2) appropriate tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone chemical combination provided by the invention is weighed
Object is dissolved with n,N-Dimethylformamide, is added a small amount of Tween 80 emulsifier, is stirred evenly, and quantitative clear water is added, is configured to
Required concentration, if coordinative solvent and clear water are control；(3) processing mode: test material sows soil treatment before next day progress seedling, list
Leaf test material is long to long to 21 heart stage of 1 leaf, dicotyledonous test material leaf periods progress stem and leaf treatment after seedlings；(4) quantitative by setting dosage
It pipettes medical fluid and carries out that cauline leaf is spraying and soil spraying treatment, be respectively to compare with spraying solvent and clear water；(5) processing test material is placed in
Hot-house culture；(6) visually upper grown situation according to investigation result calculates each chemical combination as follows after handling 15-25 days
Preventive effect of the object to weeds: preventive effect (%)=100* (control plant height-processing plant height)/control plant height；(7) weeding is carried out according to preventive effect
Activity classification: A grades of preventive effect > 90%, B grades of preventive effects 75~90%, C grades of preventive effects 50~75%, D grades of preventive effects 25~50%, E grades anti-
Imitate < 25%.The result shows that the compounds of this invention, under 5g/ mus of dosage, all compounds are selective to monocotyledon weed
Activity of weeding, wherein 1,4 pair of monocotyledon weed cauline leaf process of compound mostly has A grades of activity of weeding, and compound 1 is to unifacial leaf
Weeds soil treatment all has A grades of activity of weeding, and compound 2 all has B grades of activity, compound to monocotyledon weed cauline leaf process
3 pairs of monocotyledon weed cauline leaf process all have C grades of activity, and partial results are as follows.
Claims (5)
1. a kind of tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound, which is characterized in that the Tetrahydroisoquinoli-
The concrete structure formula of quinoline -2- base aryloxyphenoxy alkyl ketone compound are as follows:
2. tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound described in claim 1 includes R type isomers.
3. tetrahydroisoquinoline -2- base aryloxyphenoxy alkyl ketone compound described in claim 1 is on preparing herbicide
Using.
4. application as claimed in claim 3, which is characterized in that the weeds of the herbicide action are gramineae weed, specifically
For herba digitariae, barnyard grass, herba setariae viridis, hard grass , Wang grass, herba bromi japonici, amur foxtail, Triticum tauschii, alkali thatch, stinkgrass flower, wild avena sativa, rye grass.
5. application as claimed in claim 3, which is characterized in that the dosage of the herbicide is 5 grams/acre.
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|---|---|---|---|---|
| US4046553A (en) * | 1974-10-17 | 1977-09-06 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal compound, herbicidal composition containing the same and method of use thereof |
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