CN1849887A - Fluorine-contained diphenyl ether herbicide - Google Patents

Fluorine-contained diphenyl ether herbicide Download PDF

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Publication number
CN1849887A
CN1849887A CN 200510009915 CN200510009915A CN1849887A CN 1849887 A CN1849887 A CN 1849887A CN 200510009915 CN200510009915 CN 200510009915 CN 200510009915 A CN200510009915 A CN 200510009915A CN 1849887 A CN1849887 A CN 1849887A
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fluoro
trifluoro
methoxyphenyl
chloro
fluorine
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Chinese (zh)
Inventor
孙志忠
高金胜
侯艳君
于颖惠
马东升
陈亚杰
纪晓红
张宏坤
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Heilongjiang Univ
Heilongjiang University
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Heilongjiang University
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Abstract

The present invention relates to a weedicide containing fluorodiphenyl ether. Said invention provides its structure general formula. Said weedicide has high activity for killing broad-leaf weeds and gramineous weeds.

Description

Fluorine-containing diphenyl ether herbicide
Technical field:
The invention belongs to field of fine chemical, be specifically related to pesticide herbicide.
Background technology:
Diphenyl ether (diphenyl ether, DEP) weed killer herbicide is from initial stage sixties Rohm; Haas company finds behind the nitrofen and the main weed killer herbicide of a class that grows up.The compound of at present existing many diphenyl ethers has been used as weed killer herbicide and has used, as: acifluorfen (acifluorfen DE2311638), fluoroglycofen-ethyl (fluoroglycofen-ethyl, EP20052), fomesafen (fomesafen, EP3416), ethoxyfenethyl (ethoxyfen-ethyl, DE3943015), and lactofen (lactofen EP20052), Oxyfluorfen (oxyfluorfen, US3798276) etc.Although existing at present many diphenyl ether herbicides are being used, but the herbicidal effect of many type diphenyl ether compounds has very big difference, if and the structure of this compounds has very little difference, the difference of the activity of weeding character of its performance will be very big, can't singly make an explanation from chemical constitution at present about this point.Also just be based on this point, at present to the exploitation of diphenyl ether noval chemical compound also in constantly carrying out, expectation can be developed the more novel herbicide kind of high activity, greater security.
Summary of the invention:
Existing weed killer herbicide activity of weeding is low, the shortcoming of poor stability in order to solve in the present invention, on the basis of former studies, after in the diphenyl ether structure, introducing fluorine atom, change the structure of other groups, obtain a series of new fluorine-containing diphenyl ether compounds, and by activity of weeding screening, develop have efficient, low toxicity, new fluorine-containing diphenyl ether herbicide cheaply.The general structure of fluorine-containing diphenyl ether herbicide of the present invention is:
Figure A20051000991500041
Wherein: x is chlorine, fluorine or nitro; Y is a fluorine atom; R is hydroxyl, sodium salt, sylvite, ammonium salt, various C 1～C 12Alkoxyl, various C 1～C 5The sulfydryl that amido that replaces or various group replace etc., above-claimed cpd to bud after control broad leaved weed and grassy weed have activity of weeding preferably.The concrete structure of the fluorine-containing diphenyl ether herbicide that the present invention synthesizes is as shown in table 1:
Table 1
Figure A20051000991500051
The present invention to the carrying out of the sodium salt of synthetic 26 kinds of noval chemical compounds and compound 1 the activity of weeding test, at ambient temperature Preliminary Determination the herbicidal effect of their (each drug dose 10,5,2.5g/ mu) to five kinds of weeds, wherein these 5 kinds of weeds are barnyard grass grass, lady's-grass, leaf mustard, little lamb's-quarters, Amaranthus retroflexus, find behind bud under the 20 gram/mu dosage grassy weed and broad leaved weed in various degree activity all.In handling back 9 days, compound 1～26 has all showed activity of weeding in various degree, and the preventive effect majority of compounds to 5 kinds of targets under the dosage of 75g/ha can both reach more than 70%; Compound 1 and sodium salt thereof, compound 3,4 reach more than 70% the broad leaved weed preventive effect under 37.5g/ha dosage, concrete result of the test such as table 2.As can be seen, the sodium salt of the acid of this compound has active preferably than its free acid on structure and the activity relationship, and the activity of ester is higher than acid amides, has the ester of less group in ester, has active preferably as methyl esters.
Table 2
Numbering Concentration (g/a) Lady's-grass The barnyard grass grass Leaf mustard Amaranthus retroflexus Little lamb's-quarters
1 2.5 20 10 50 40 30
5 30 15 70 80 30
10 60 30 80 90 90
2 2.5 30 10 90 90 70
5 70 60 100 100 100
10 90 90 100 100 100
3 2.5 80 40 80 90 70
5 95 70 90 100 75
10 100 95 100 100 100
4 2.5 60 10 20 40 50
5 90 60 70 80 70
10 100 40 95 100 70
5 2.5 20 0 30 10 20
5 40 10 50 60 30
10 80 20 80 80 30
6 2.5 20 0 0 10 10
5 50 10 40 30 30
10 80 20 40 30 30
7 2.5 10 0 20 20 0
5 30 0 30 40 0
10 70 10 60 80 30
8 2.5 20 0 0 0 0
5 20 0 30 20 30
10 40 0 50 80 80
9 2.5 20 0 0 0 0
5 30 0 30 10 40
10 40 20 40 60 60
10 2.5 10 0 20 10 0
5 30 10 50 30 20
10 50 40 70 90 20
11 2.5 10 0 0 0 0
5 20 0 30 20 20
10 30 0 50 80 70
12 2.5 0 0 0 0 0
5 10 10 0 10 20
10 30 30 10 30 30
13 2.5 0 0 0 0 0
5 0 0 0 0 0
10 10 30 10 20 40
14 2.5 20 0 40 40 20
5 70 10 80 70 30
10 90 10 100 90 80
15 2.5 20 0 30 20 10
5 20 30 70 90 20
10 70 20 90 90 30
16 2.5 10 0 20 30 20
5 20 0 50 40 30
10 40 10 90 90 70
17 2.5 10 0 30 20 10
5 20 0 70 50 30
10 30 10 90 70 40
18 2.5 10 0 0 0 0
5 10 0 0 10 20
10 20 30 20 30 30
19 2.5 0 0 0 0 0
5 0 10 0 20 20
10 30 20 30 30 40
20 2.5 0 0 0 0 0
5 10 0 10 10 10
10 20 40 30 30 40
21 2.5 10 0 0 0 0
5 20 0 0 20 0
10 40 30 0 30 20
22 2.5 10 0 30 40 20
5 20 10 50 60 30
10 40 20 60 70 80
23 2.5 30 10 40 60 40
5 40 20 60 80 50
10 70 50 70 90 80
24 2.5 60 30 60 50 40
5 70 50 70 80 65
10 80 75 90 90 70
25 2.5 80 50 80 90 70
5 95 80 95 100 85
10 100 95 100 100 100
26 2.5 60 40 50 60 60
5 85 60 70 80 70
10 100 75 95 100 80
Embodiment:
Embodiment one: the general structure of the fluorine-containing diphenyl ether compound of present embodiment is:
Wherein: x is chlorine, fluorine or nitro; Y is a fluorine atom;
R is hydroxyl, sodium salt, sylvite, ammonium salt, various C 1～C 12Alkoxyl, various C 1～C 5The amido that replaces or the sulfydryl of various replacements etc.
Synthetic method is: obtain intermediate acid by condensation, oxidation reaction, and as 5-(2-chloro-4-4-trifluoromethylphenopendant)-2-fluobenzoic acid, and then through acidylate, resterification or amination, preparation corresponding esters or acid amides.Intermediate acid and corresponding alkali can form corresponding carboxylic acid salt.
The preparation of intermediate acid: in the preparation process of intermediate acid, at first pass through condensation reaction: with 3,4-two chlorobenzotrifluorides, 4-fluoro-3-methylphenol or derivatives thereof are according to mol ratio (0.8～1.5): 1 mixes, under certain solvent condition and Fu's acid agent condition, solvent can be dimethyl sulfoxide (DMSO), dimethylacetylamide, dimethyl formamide, sulfolane etc.; Fu's acid agent can be natrium carbonicum calcinatum, Anhydrous potassium carbonate, sodium hydroxide, potassium hydroxide etc.; Reaction temperature is 120～180 ℃, and the reaction time is 1～20 hour, filters decompression and solvent recovery then, obtains the residue intermediate; Secondly in peroxidization, in above-mentioned residue intermediate, add red fuming nitric acid (RFNA), catalyzer, its intermediate, red fuming nitric acid (RFNA), catalyst molar ratio are 1: 14: 0.02～0.05, catalyzer can be vanadic anhydride, ammonium metavanadate etc., reaction temperature is 160～175 ℃, and the reaction time is 2～18 hours, filters then, handling, obtain faint yellow intermediate acid through soda acid.
Acylation reaction:
Above-mentioned intermediate acid 5-(2-chloro-4-the 4-trifluoromethylphenopendant)-2-fluobenzoic acid that obtains is joined in the solvent, add corresponding chlorination reagent again, the control reaction temperature was 20 ℃～120 ℃ reactions 2～10 hours, wherein solvent for use can be carrene, dichloroethane, benzene, toluene, chlorobenzene, atent solvents such as dimethylbenzene; Chlorination reagent can be thionyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride etc.; The mol ratio of raw material and chlorination reagent 1: 1～1: 1.5, the w/v of raw material and solvent are 1: 1～1: 10.Reaction is removed excessive chlorination reagent and solvent after finishing, and the acylate that obtains directly can be used for the next step, need not be further purified processing.
Esterification or aminating reaction:
In above-mentioned acylate system, add solvent and corresponding alcohol or amine and Fu's acid agent, and then 20 ℃～100 ℃ reactions 2～10 hours, wherein solvent for use can be carrene, dichloroethane, benzene, toluene, chlorobenzene, atent solvents such as dimethylbenzene; The w/v of raw material and solvent is 1: 1～1: 10; Fu acid agent can be Anhydrous potassium carbonate, natrium carbonicum calcinatum, triethylamine, pyridine, DMF etc., and its consumption is an acylate and the mol ratio of the sour agent of Fu 1: 1～1: 1.5.Reaction finishes the back can obtain final product by general processing.
In the process that forms acid amides, also can adopt the one-step method reaction; with 5-(2-chloro-4-4-trifluoromethylphenopendant)-2-fluobenzoic acid and corresponding replacement amine, acylating agent, solvent; the control reaction temperature was 20 ℃～120 ℃ reactions 2～10 hours; wherein solvent for use can be carrene, dichloroethane, benzene, toluene, chlorobenzene; atent solvents such as dimethylbenzene, chlorination reagent can be phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride etc.Other conditions are the same, and reaction finishes the back can obtain final product by general processing.
Salt-forming reaction:
Add certain amount of solvent in intermediate acid 5-(2-chloro-4-4-trifluoromethylphenopendant)-2-fluobenzoic acid, with the aqueous slkali reaction with same mole, temperature is that room temperature arrives solvent refluxing, 1～4 hour reaction time, and frequently the water that generates is removed by water knockout drum.Wherein alkali can be sodium hydroxide, potassium hydroxide, sodium carbonate, potash, ammoniacal liquor, and concentration is 5～50%, and the solvent that is adopted is toluene, cyclohexane, benzene, dichloroethane etc.Reaction finishes the back can obtain corresponding sodium, potassium, amine salt by general processing product.
The synthetic reaction equation is:
Figure A20051000991500101
Embodiment two: working as x in the present embodiment is the chlorine atom, and y is a fluorine atom, and when R was sodium salt, particular compound was 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-Sodium Benzoate.
Embodiment three: working as x in the present embodiment is the chlorine atom, and y is a fluorine atom, and when R was sylvite, particular compound was 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-Potassium Benzoate.
Embodiment four: working as x in the present embodiment is the chlorine atom, and y is a fluorine atom, and when R was ammonium salt, particular compound was 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-ammonium benzoate.
Embodiment five: working as x in the present embodiment is the chlorine atom; y is a fluorine atom; when R is amido; particular compound is 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-N-cyclopropyl-2-fluoro-benzamide, 5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-N-normal-butyl-2-fluoro-benzamide or 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-N-mesyl-2-fluoro-benzamide.
Embodiment six: working as x in the present embodiment is the chlorine atom; y is a fluorine atom; when R is alkoxyl; particular compound is O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl]-the L-ethyl lactate; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] ethyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] propyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] isopropyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] isopentyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] isobutyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] the propylene ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl]-pentyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] heptyl ester; O-[5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl] butyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] lauryl or O-[5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl] secondary butyl ester.
Embodiment seven: working as x in the present embodiment is the chlorine atom, and y is a fluorine atom, and when R was sulfydryl, particular compound was 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-tert-butyl group thioesters.
Embodiment eight: in the present embodiment when x be fluorine or nitro, y be fluorine atom, when R is hydroxyl, particular compound is 5-(2-nitro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoic acid or 5-(2-fluoro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoic acid.
Embodiment nine: in the present embodiment when x be nitro, y be fluorine atom, when R is alkoxyl, particular compound is O-[5-(2-nitro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl] methyl esters.
Embodiment ten: in the present embodiment when x be fluorine atom, y be fluorine atom, when R is alkoxyl; particular compound is O-[5-(2-fluoro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] methyl esters or O-[5-(2-fluoro-α; α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl] ethyl ester.
Embodiment 11: present embodiment is with 2-fluoro-5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl) toluene synthesize example: in the 500ml four-hole bottle, add 82% potassium hydroxide 28g (0.41mol), 4-fluoro-3-cresols 50.4g (0.4mol), heating, dissolving, add entrainer 150ml, azeotropic water removing; Reclaim solvent, be cooled to room temperature, add dimethyl sulfoxide (DMSO) 180ml, 3,4-two chlorobenzotrifluoride 86.0g (0.4mol) stir, heat 135～140 ℃ of reactions, the gas-chromatography monitoring.Reaction finishes, and is cooled to room temperature, filters, and with dimethyl sulfoxide (DMSO) washing leaching cake twice, decompression steams dimethyl sulfoxide (DMSO), gets light yellow oily liquid crude product, about 85.0g, yield 70.0%.
Synthesizing of other intermediates 2-fluoro-5-(2-nitro-α, α, α-trifluoro p-methoxyphenyl) toluene, 2-fluoro-5-(2-fluoro-α, α, α-trifluoro p-methoxyphenyl) toluene is identical with above-mentioned method.
Embodiment 12: present embodiment is with the benzoic example that synthesizes of 2-fluoro-5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl): add above-mentioned intermediate 2-fluoro-5-(2-chloro-α in the 250ml four-hole bottle, α, α-trifluoro p-methoxyphenyl) toluene 30.5g (0.1mol) adds vanadic anhydride 0.3g, stirs, be heated to 165 ℃, drip red fuming nitric acid (RFNA), temperature is controlled at 165～175 ℃, and reaction 6～8h is after reaction is finished, temperature is reduced to room temperature, filter, solid dissolves with 5% sodium hydroxide solution, filters, using the watery hydrochloric acid acidifying, filter, washing gets white powder solid 25.5g to neutral, yield 75.5%, 153～155 ℃ of fusing points.
Other intermediates 2-fluoro-5-(2-nitro-α, α, α-trifluoro p-methoxyphenyl) benzoic acid, 2-fluoro-5-(2-fluoro-α, α, α-trifluoro p-methoxyphenyl) are benzoic synthetic identical with above-mentioned method.
Embodiment 13: present embodiment is with 2-fluoro-5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl) methyl benzoate synthesize example: in the 250ml there-necked flask, add 4.0g (0.0121mol) 2-fluoro-5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl) benzoic acid, 70ml toluene, the 20g thionyl chloride, added hot reflux 6 hours, excessive thionyl chloride is removed in decompression, drip the mixture of 15g methyl alcohol and 10ml triethylamine under the room temperature, added hot reflux then 8 hours, filter then, filtrate is used diluted acid respectively, washed several times with water, decompression steams solvent and promptly gets light brown oily liquid, yield 90%, purity 90% (HLPC).
Compound 3～17,22～26 adopts corresponding ethanol, propyl alcohol, isopropyl alcohol, butanols, isobutanol, sec-butyl alcohol, amylalcohol, isoamyl alcohol, hexanol, tip-nip, allyl alcohol, glycol monoethyl ether, diethylene glycol monomethyl ether, tert-butyl mercaptan to replace above-mentioned methyl alcohol, synthetic as stated above then corresponding ester.
Embodiment 14: present embodiment is with N, N-dimethyl-2-fluoro-5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl) benzamide synthesize example: in the 250ml there-necked flask, add 8.0g (0.024mol) 2-fluoro-5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl) benzoic acid, the 70ml dichloroethane, the 20g thionyl chloride, added hot reflux 6 hours, excessive thionyl chloride is removed in decompression, at additional 50ml dichloroethane, add the mixture of 3.0g dimethylamine hydrochloride and 5ml triethylamine then, added hot reflux then 8 hours, filter then, filtrate is used diluted acid respectively, washed several times with water, the organic layer anhydrous sodium sulfate drying, decompression steams solvent and promptly gets brown oily liquids, yield 80%, purity 92% (HLPC).
Compound 18～21 adopts corresponding isopropylamine, n-butylamine, cyclopropylamine to replace above-mentioned dimethylamine hydrochloride, synthetic as stated above then corresponding amide.
Embodiment 15: present embodiment is with N-normal-butyl-2-fluoro-5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl) benzamide synthesize example: in the 250ml there-necked flask, add 33.3g (0.1mol) 2-fluoro-5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl) after benzoic acid, 8.0g n-butylamine and 12ml triethylamine, 100ml dichloroethane mix, heat up 40～50 ℃, drip the 8.0g phosphorus oxychloride, added hot reflux then 4 hours; Add the low amounts of water hydrolysis then, organic layer washes neutrality again with water, uses anhydrous sodium sulfate drying, and decompression steams the white solid of solvent, yield 89%, purity 95% (HLPC).
Compound 18～21 adopts corresponding isopropylamine, n-butylamine, cyclopropylamine to replace above-mentioned dimethylamine hydrochloride, synthetic as stated above then corresponding amide.
Embodiment 16: present embodiment is with 2-fluoro-5-(2-nitro-α, α, α-trifluoro p-methoxyphenyl) Sodium Benzoate synthesize example: in the 250ml four-hole bottle, add 50% sodium hydroxide (0.05mol) aqueous solution, add 70ml cyclohexane and 2-fluoro-5-(2-chloro-4-4-trifluoromethylphenopendant) benzoic acid 16.7g (0.05mol), agitating heating backflow 20min, divide water then, after about 2h divides water to finish, cooling, filter, get white solid 17.2g, yield 95%, purity 97.6%.
Compound 2 relevant sylvite and ammonium salts synthesize with quadrat method according to above-mentioned.

Claims (10)

1, fluorine-containing diphenyl ether herbicide is characterized in that its general structure is:
Wherein: x is chlorine, fluorine or nitro; Y is a fluorine atom; R is hydroxyl, sodium salt, sylvite, ammonium salt, C 1～C 12Alkoxyl, C 1～C 5The sulfydryl that amido that replaces or various group replace.
2, fluorine-containing diphenyl ether herbicide according to claim 1, it is characterized in that x be chlorine, fluorine or nitro, y be fluorine atom, when R is hydroxyl, particular compound is 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoic acid, 5-(2-nitro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoic acid or 5-(2-fluoro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoic acid.
3, fluorine-containing diphenyl ether herbicide according to claim 1, it is characterized in that x be chlorine atom, y be fluorine atom, when R is sodium salt, particular compound is 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-Sodium Benzoate.
4, fluorine-containing diphenyl ether herbicide according to claim 1, it is characterized in that x be chlorine atom, y be fluorine atom, when R is sylvite, particular compound is 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-Potassium Benzoate.
5, fluorine-containing diphenyl ether herbicide according to claim 1, it is characterized in that x be chlorine atom, y be fluorine atom, when R is ammonium salt, particular compound is 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-ammonium benzoate.
6, fluorine-containing diphenyl ether herbicide according to claim 1; it is characterized in that x be chlorine atom, y be fluorine atom, when R is amido; particular compound is 5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-N-cyclopropyl-2-fluoro-benzamide, 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-N-normal-butyl-2-fluoro-benzamide or 5-(2-chloro-α; α, α-trifluoro p-methoxyphenyl)-N-mesyl-2-fluoro-benzamide.
7; fluorine-containing diphenyl ether herbicide according to claim 1; it is characterized in that x is the chlorine atom; y is a fluorine atom; when R is alkoxyl; particular compound is O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl]-the L-ethyl lactate; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] ethyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] propyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] isopropyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] isopentyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] isobutyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] the propylene ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl]-pentyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] heptyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] butyl ester; O-[5-(2-chloro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] lauryl or O-[5-(2-chloro-α; α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl] secondary butyl ester.
8, fluorine-containing diphenyl ether herbicide according to claim 1, it is characterized in that x be chlorine atom, y be fluorine atom, when R is sulfydryl, particular compound is 5-(2-chloro-α, α, α-trifluoro p-methoxyphenyl)-tert-butyl group thioesters.
9, fluorine-containing diphenyl ether herbicide according to claim 1, it is characterized in that x be nitro, y be fluorine atom, when R is alkoxyl, particular compound is O-[5-(2-nitro-α, α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl] methyl esters.
10, fluorine-containing diphenyl ether herbicide according to claim 1; it is characterized in that x be fluorine atom, y be fluorine atom, when R is alkoxyl; particular compound is O-[5-(2-fluoro-α; α; α-trifluoro p-methoxyphenyl)-and 2-fluoro-benzoyl] methyl esters or O-[5-(2-fluoro-α; α, α-trifluoro p-methoxyphenyl)-2-fluoro-benzoyl] ethyl ester.
CN 200510009915 2005-04-22 2005-04-22 Fluorine-contained diphenyl ether herbicide Pending CN1849887A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101407462B (en) * 2007-10-09 2011-07-20 中国中化股份有限公司 Diphenyl ether compound and use thereof
CN101747202B (en) * 2008-12-11 2013-03-27 中国中化股份有限公司 2-chloro-benzoate compound and application thereof
CN105985246A (en) * 2015-03-05 2016-10-05 湖南化工研究院有限公司 Diphenyl-ether compound with weeding or insecticidal or bactericidal activity

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101407462B (en) * 2007-10-09 2011-07-20 中国中化股份有限公司 Diphenyl ether compound and use thereof
CN101747202B (en) * 2008-12-11 2013-03-27 中国中化股份有限公司 2-chloro-benzoate compound and application thereof
CN105985246A (en) * 2015-03-05 2016-10-05 湖南化工研究院有限公司 Diphenyl-ether compound with weeding or insecticidal or bactericidal activity
CN105985246B (en) * 2015-03-05 2018-04-10 湖南化工研究院有限公司 Has the diphenyl ether compound of weeding, desinsection or bactericidal activity

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