CN1276787A - Substd. N-aryl-O-aryloxyalkyl carbamates and their use as herbicides - Google Patents

Substd. N-aryl-O-aryloxyalkyl carbamates and their use as herbicides Download PDF

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Publication number
CN1276787A
CN1276787A CN 98810378 CN98810378A CN1276787A CN 1276787 A CN1276787 A CN 1276787A CN 98810378 CN98810378 CN 98810378 CN 98810378 A CN98810378 A CN 98810378A CN 1276787 A CN1276787 A CN 1276787A
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group
represent
replacement
methyl
different
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H·J·里贝尔
J·R·扬森
P·海特坎珀
M·多林格
M·W·德鲁斯
I·维特肖洛夫斯基
E·R·格辛
J·克鲁斯
S·勒尔
R·A·迈尔斯
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof

Abstract

The invention relates to novel substituted n-aryl-o-aryloxyalkyl carbamates of general formula (I), wherein m represents the numbers 0, 1 or 2, n represents the numbers 0, 1, 2, 3 or 4, R<1> represents cyano, halogen or alkyl or alkoxy, said alkyl or alkoxy being optionally substituted by cyano, halogen or C1-C4 alkoxy and each having 1 to 4 carbon atoms; R<2> represents alkyl optionally substituted by cyano, halogen or C1-C4 alkoxy and each having 1 to 4 carbon atoms, R<3> represents cyano, fluorine, bromine, iodine or alkyl, alkoxy or alkoxy carbonyl optionally substituted by cyano, halogen or C1-C4 alkoxy, each having up to 4 carbon atoms; and R<4> represents cyano, bromine, iodine or alkyl, alkoxy or alkoxy carbonyl optionally substituted by cyano, halogen or C1-C4 alkoxy, each having up to 4 carbon atoms, excluding the compound N-(2-methoxy-5-methyl-phenyl)-O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl]-carbamate. The invention also relates to methods for producing the inventive substituted n-aryl-o-aryloxyalkyl carbamates and to their use as herbicides.

Description

The N-arylamino formic acid O-aryloxy alkyl ester that replaces and as herbicide applications
The present invention relates to novel substituted N-arylamino formic acid O-aryloxy alkyl ester preparation and as herbicide applications.
The O-aryloxy N-aryl-carbamate of known some replacement, for example, compound O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] N-(2-chloro-phenyl)-carbamate, O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] N-(2-trifluoromethyl-phenyl)-carbamate and O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] N-(3-trifluoromethyl-phenyl)-carbamate, have herbicidal performance (referring to, for example US-A-5 099 059 and US-A-5152 827).Yet the weeding activity of these known compounds is not always satisfactory.
Therefore, the invention provides the O-aryloxy alkyl N-aryl-carbamate of the replacement of novel general formula (I), Wherein m represents numeral 0,1 or 2, and n represents numeral 0,1,2,3 or 4, and its prerequisite is that under each situation, m and n sum are at least 1, R 1Represent cyano group, halogen or all can choose wantonly by cyano group-, halogen-or C 1-C 4The alkyl or the alkoxyl group that respectively have 1 to 4 carbon atom of-alkoxyl group-replacement, R 2Representative optional by cyano group-, halogen-or C 1-C 4The alkyl with 1 to 4 carbon atom of-alkoxyl group-replacement, R 3Represent cyano group, fluorine, bromine, iodine or all can choose wantonly by cyano group-, halogen-or C 1-C 4The alkyl, alkoxyl group or the alkoxy carbonyl that respectively have 1 to 4 carbon atom of-alkoxyl group-replacement, and-represent at m under 1 or 2 the situation-also represent chlorine, and R 4Represent cyano group, bromine, iodine or all can choose wantonly by cyano group-, halogen-C 1-C 4The alkyl, alkoxyl group or the alkoxy carbonyl that respectively have 1 to 4 carbon atom of-alkoxyl group-replacement, and-represent under 1 or 2 the situation-also represent fluorine or chlorine at m, except prior art compound O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] N-(2-methoxyl group 5-methyl-phenyl)-carbamate-referring to, US-A-5099059 and US-A-5152827, it is left out the compound sequence number 40-in its table 1.
General formula of the present invention (I) compound contains the carbon atom of asymmetric replacement and therefore can have different enantiomorph (R-and S-configuration) or diastereomer.The present invention relates to the different possible independent enantiomorph or the stereoisomer form of general formula (I) compound, and the mixture that relates to these steric isomer compounds.
In definition, hydrocarbon chain is as alkyl-and when making up with heteroatoms, as at alkoxyl group-respectively be straight or branched.
The present invention preferably provides formula (I) compound, and wherein m represents numeral 0,1 or 2, and n represents numeral 0,1,2,3 or 4, and its prerequisite is that under each situation, m and n sum are at least 1, R 1Represent cyano group, fluorine, chlorine, bromine or all can choose wantonly by cyano group-, fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or isopropoxy, R 2Representative all can choose wantonly by cyano group-, fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacements, ethyl, just-or sec.-propyl, just-, different-, the second month in a season-or the tertiary butyl, R 3Represent cyano group, fluorine, bromine, iodine or all can choose wantonly by cyano group-, fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or isopropoxy, methoxycarbonyl, ethoxy carbonyl, just-or different-propoxycarbonyl, and-represent at m under 1 or 2 the situation-also represent chlorine, and R 4Represent cyano group, bromine, iodine or all can choose wantonly by cyano group-, fluorine, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or isopropoxy, just-, different-, secondary-or tert.-butoxy, methoxycarbonyl, ethoxy carbonyl, just-or different-propoxycarbonyl, and-represent under 1 or 2 the situation-also represent fluorine or chlorine at m, except prior art compound O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] N-(2-methoxyl group 5-methyl-phenyl)-carbamate-referring to, US-A-5099059 and US-A-5152827, it is left out the compound sequence number 40-in its table 1.
In particular, the present invention relates to formula (I) compound, wherein m represents numeral 0 or 1, and n represents numeral 0,1 or 2, and its prerequisite is that under each situation, m and n sum are at least 1, R 1Represent cyano group, fluorine, chlorine, bromine or all can choose methyl, ethyl, the methoxy or ethoxy that replaces by fluoro-or chloro-, R wantonly 2Representative all can choose wantonly by fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or sec.-propyl, R 3Represent cyano group, fluorine, bromine or all can choose wantonly by fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, methoxyl group, oxyethyl group, just-or isopropoxy, methoxycarbonyl, ethoxy carbonyl, just-or different-propoxycarbonyl, and-represent at m under 1 the situation-also represent chlorine, and R 4Represent cyano group, bromine, iodine or all can choose wantonly by fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, methoxyl group, oxyethyl group, just-or isopropoxy, methoxycarbonyl, ethoxy carbonyl, just-or different-propoxycarbonyl, and-represent under 1 the situation-also represent fluorine or chlorine at m, except prior art compound O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] N-(2-methoxyl group 5-methyl-phenyl)-carbamate-referring to, US-A-5099059 and US-A-5152827, it is left out the compound sequence number 40-in its table 1.
General or preferred group definition above-mentioned is suitable for formula (I) end product, and correspondingly, also is suitable for starting raw material or intermediate required under each preparation situation.These group definition can mutually combine as required,, comprise the combination between preferable range above-mentioned that is.
The O-aryloxy alkyl N-aryl-carbamate of the new replacement of general formula (I) shows strong and and weeding activity optionally.
Surprising is that the O-aryloxy alkyl N-aryl-carbamate of the new replacement of general formula (I) is than prior art compound O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] N-(2-chloro-phenyl)-carbamate, O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] N-(2-trifluoromethyl-phenyl)-carbamate and O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] the N-weeding activity that (3-methyl fluoride-phenyl)-carbamate is much better than.
Some general formula (I) compound also shows fungicidal and insecticidal activity.
The grouping of formula of the present invention (I) examples for compounds is listed in hereinafter.
Group 1
Figure A9881037800091
Herein, n, R 3And R 4Have the connotation that for example hereinafter provides:
?R 3 (position) (R 4) n ?R 3 (position) (R 4) n ?R 3 (position) (R 4) n
?CH 3 (3)CH 3 ?CH 3 (4)CH 3 ?CH 3 (5)CH 3
?CH 3 (6)CH 3 ?CH 3 (6)C 2H 5 ?CH 3 (4，5) (CH 3) 2
?CH 3 (3，5) (CH 3) 2 ?CH 3 (4，6) (CH 3) 2 ?CH 3 (4)CH 3(6)C 2H 5
?CH 3 (3)CF 3 ?CH 3 (4)CF 3 ?CH 3 (5)CF 3
?CH 3 (3)Br ?CH 3 (4)Br ?CH 3 (5)Br
?CH 3 (3)CN ?CH 3 (4)CN ?CH 3 (5)CN
?CH 3 (3)OCH 3 ?CH 3 (4)OCH 3 ?CH 3 (5)OCH 3
?F (3)CH 3 ?F (4)CH 3 ?F (5)CH 3
?F (6)CH 3 ?F (6)C 2H 5 ?F (4，5) (CH 3) 2
?F (3，5) (CH 3) 2 ?F (4，6) (CH 3) 2 ?F (4)CH 3(6)C 2H 5
?F (3)CF 3 ?F (4)CF 3 ?F (5)CF 3
?F (3)Br ?F (4)Br ?F (5)Br
?F (3)CN ?F (4)CN ?F (5)CN
?F (3)OCH 3 ?F (4)OCH 3 ?F (5)OCH 3
?Br (3)CH 3 ?Br (4)CH 3 ?Br (5)CH 3
?R 3 (position) (R 4) n ?R 3 (position) (R 4) n ?R 3 (position) (R 4) n
?Br (6)CH 3 ?Br (6)C 2H 5 ?Br (4，5) (CH 3) 2
?Br (3，5) (CH 3) 2 ?Br (4，6) (CH 3) 2 ?Br (4)CH 3(6)C 2H 5
?Br (3)CF 3 ?Br (4)CF 3 ?Br (5)CF 3
?Br (3)Br ?Br (4)Br ?Br (5)Br
?Br (3)CN ?Br (4)CN ?Br (5)CN
?Br (3)OCH 3 ?Br (4)OCH 3 ?Br (5)OCH 3
?CF3 (3)CH 3 ?CF 3 (4)CH 3 ?CF 3 (5)CH 3
?CF 3 (4)Br ?CF 3 (4)OCH 3 ?CF 3 (4)CN
?CF 3 (3)CF 3 ?CF 3 (4)CF 3 ?CF 3 (5)CF 3
?OCH 3 (3)CH 3 ?OCH 3 (4)CH 3 ?OCH 3 (5)OC 2H 5
?OCH 3 (6)CH 3 ?OCH 3 (6)C 2H 5 ?OCH 3 (4，5) (CH 3) 2
?OCH 3 (3，5) (CH 3) 2 ?OCH 3 (4，6) (CH 3) 2 ?OCH 3 (4)CH 3(6)C 2H 5
?OCH 3 (3)CF 3 ?OCH 3 (4)CF 3 ?OCH 3 (5)CF 3
?OCH 3 (3)Br ?OCH 3 (4)Br ?OCH 3 (5)Br
?OCH 3 (3)CN ?OCH 3 (4)CN ?OCH 3 (5)CN
?OCH 3 (3)OCH 3 ?OCH 3 (4)OCH 3 ?OCH 3 (5)OCH 3
?OCH 3 (3)COOEt ?OCH 3 (4)COOEt ?OCH 3 (5)COOEt
Group 2
Figure A9881037800121
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 3 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 4 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 5
Figure A9881037800124
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 6
Figure A9881037800131
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 7
Figure A9881037800132
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 8 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 9 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 10
Figure A9881037800142
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 11 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 12 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 13
Figure A9881037800151
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 14 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 15
Figure A9881037800153
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 16
Figure A9881037800161
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 17 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 18 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 19 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 20
Figure A9881037800171
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 21
Figure A9881037800172
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 22
Figure A9881037800173
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 23
Figure A9881037800181
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 24 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 25
Figure A9881037800183
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 26
Figure A9881037800184
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 27
Figure A9881037800191
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 28 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 29
Figure A9881037800193
Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
Group 30 Herein, n, R 3And R 4Have and for example above organize the connotation that provides in 1.
The following acquisition of O-aryloxy alkyl N-aryl-carbamate of the replacement of novel general formula (I): if if (a) suit in the presence of reaction promoter and suit in the presence of thinner, to make general formula
The arylamines reaction of chloroformic acid aryloxy alkyl ester (II) and general formula (III) Wherein m, R 1And R 2As defined above,
Figure A9881037800203
N, R 3And R 4As defined above, if if or (b) suit in the presence of reaction promoter and suit in the presence of thinner, to make general formula
(IV) aryloxy alkanol and the reaction of the aryl isocyanate of logical formula V
Figure A9881037800204
Wherein m, R 1And R 2As defined above,
Figure A9881037800211
Wherein n, R 3And R 4As defined above.
Use, for example, [1-(2-fluoro-5-trifluoromethyl-phenoxymethyl)-propyl group] chloro-formic ester and 2-amino-4-ethyl-methyl benzoate are as starting raw material, and the reaction path in the inventive method (a) can illustrate with following reaction formula:
Figure A9881037800212
Use, for example, 2-(3,5-couple-trifluoromethyl-phenoxy group)-1-methyl-ethanol and 2-bromo-6-methyl-phenyl isocyanate are as starting raw material, and the reaction path in the inventive method (b) can illustrate with following reaction formula:
Formula (II) is provided at the General Definition that is used as the chloroformic acid aryloxy aryl ester of starting raw material in the inventive method (a) for preparing formula of the present invention (I) compound.In formula (II), m, R 1And R 2Each preferably or particularly has m, the R that had mentioned already in the relevant description of formula of the present invention (I) compound above 1And R 2Preferred or particularly preferred connotation.
Formula (II) starting raw material be known and/or can by known method preparation itself (referring to, US-A-5099059, US-A-5152827, US-A-5399545).
Formula (III) is provided in the inventive method (a) another General Definition as the arylamines of starting raw material.In formula (III), n, R 3And R 4Preferably or particularly have the n, the R that in the relevant description of formula of the present invention (I) compound above, had mentioned already 3And R 4Preferred or particularly preferred connotation.
Formula (III) starting raw material is known synthetic compound.
Formula (IV) is provided at the General Definition of the aryloxy alkanol of the starting raw material that is used as the compound for preparing general formula (I) in the inventive method (b).In formula (IV), m, R 1And R 2Each preferably or particularly has m, the R that had mentioned already in the relevant description of formula of the present invention (I) compound above 1And R 2Preferred or particularly preferred connotation.
General formula (IV) starting raw material be known and/or can by known method preparation itself (referring to, US-A-5099059, US-A-5152827, US-A-5399545).
Formula V is provided at the General Definition that is used as the aryl isocyanate of starting raw material in the inventive method (b).In formula V, n, R 3And R 4Preferably or particularly have the n, the R that in the relevant description of formula of the present invention (I) compound above, had mentioned already 3And R 4Preferred or particularly preferred connotation.
The formula V starting raw material is known synthetic compound.
Be suitable for method (a) and reaction auxiliary (b) normally conventional inorganic or organic bases or acid acceptor.These materials preferably include the acetate of basic metal or alkaline-earth metal, amide, carbonate, supercarbonate, hydride, oxyhydroxide or alkoxide are as sodium acetate, potassium acetate or lime acetate, lithamide, ammonification sodium, ammonification potassium or ammonification calcium, yellow soda ash, salt of wormwood or lime carbonate, sodium bicarbonate, saleratus or Calcium hydrogen carbonate, lithium hydride, sodium hydride, potassium hydride KH or hydrolith, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, methyl alcohol, ethanol, just or the sodium of Virahol, just-, different-, secondary-or the sodium salt or the methyl alcohol of the trimethyl carbinol, ethanol, just-or Virahol, just-, different-, secondary-or the sylvite of the trimethyl carbinol; Also has alkaline organic nitrogen compound in addition, as, Trimethylamine 99, triethylamine, tripropyl amine, Tributylamine, ethyl-Diisopropylamine, N, N-dimethyl-cyclo-hexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, accelerine, N, N-dimethyl-benzyl amine, pyridine, the 2-methyl-, the 3-methyl-, the 4-methyl-, 2, the 4-dimethyl-, 2, the 6-dimethyl-, 3, the 4-dimethyl-and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidines, 1,4-diazabicylo [2,2,2]-octane (DABCO), 1,5-diazabicylo [4,3,0]-ninth of the ten Heavenly Stems-5-alkene (DBN) or 1,8-diazabicylo [5,4,0]-11-7-alkene (DBU).
Be suitable for carrying out particularly inert organic solvents of the inventive method (a) and thinner (b).These materials comprise the optional halogenated hydrocarbon of aliphatics particularly, alicyclic or aromatics, as, as gasoline, benzene,toluene,xylene, chlorobenzene, dichlorobenzene, sherwood oil, hexane, hexanaphthene, methylene dichloride, chloroform, tetracol phenixin; Ethers is as ether, diisopropyl ether, diox, tetrahydrofuran (THF) or glycol dimethyl ether or ethylene glycol diethyl ether; Ketone is as acetone, butanone or mibk; Nitrile is as acetonitrile, propionitrile or butyronitrile; Amides, as N, dinethylformamide, N,N-dimethylacetamide, N-methyl-formylaniline, N-Methyl pyrrolidone or HMPA; The ester class is as methyl acetate or ethyl acetate; The sulfoxide class is as dimethyl sulfoxide (DMSO); Alcohols, as methyl alcohol, ethanol, just-or Virahol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, the mixture of they and water, or pure water.
Carry out the inventive method (a) and (b) time, temperature of reaction can be carried out in wide relatively scope.Usually, reaction is at 0 ℃ to 150 ℃, preferably carries out under the temperature between 10 ℃ to 120 ℃
Method of the present invention (a) and (b) normally under normal pressure, carrying out.Yet, the inventive method also can the pressurization or the decompression under---normally 0.1 the crust to 10 the crust between pressure under carry out.
When carrying out the inventive method, adopt the roughly starting raw material of equimolar amount usually.One of yet, also can excessive relative to the earth employing reactive component.If reaction suitable, carry out in the presence of the reaction auxiliary, and reaction mixture was stirred several hours under required temperature usually normally in the thinner that is fit to.Aftertreatment be with ordinary method carry out (referring to, the preparation embodiment).
Active compound of the present invention can be used as defoliating agent, siccative, kill the cane agent and in particular as weedicide.So-called weeds with regard to it the most in the broadest sense, are interpreted as being grown in all plants in the place that should not grow.Material of the present invention is as steriland herbicide or selective herbicide depends on used amount basically.
The compounds of this invention can relevant use with for example following plants: the broadleaf weed of following dependent of dead military hero: mustard belongs to, the grass of walking alone belongs to, Bedstraw, Stellaria, Matricaria, Anthemis, Achyranthes, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, japanese bearbind belongs to, sweet potato genus, Polygonum, Daubentonia, Ambrosia, Cirsium, bristlethistle, sonchus L, Solanum, the weldering Lepidium, Herba Clinopodii Polycephali belongs to, Vandellia, lamium, Veronica, abutilon, the thorn Rumex, Datura, Viola, the weasel hemp nettle belongs to, papaver, bachelor's-button, Trifolium, Ranunculus and Dandelion, the dicotyledonous crops of following dependent of dead military hero: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, linum, sweet potato genus, vetch, Nicotiana, tomato belongs to, Arachis, Btassica, Lactuca, Cucumis and Cucurbita, the monocotyledon weed of following dependent of dead military hero: Echinochloa, setaria, Panicum, knotgrass, ladder forage spp, annual bluegrass belongs to, festuca, yard grass belongs to, Brachiaria, lolium, Brome, Avena, Cyperus, jowar belongs to, Agropyron, Cynodon, Monochoria, genus fimbristylis, arrowhead belongs to, Eleocharis, the Fischer grass belongs to, Paspalum, ischaemum, the cusp Pittosporum, talon eria, Agrostis, amur foxtail belongs to and the wind grass belongs to the monocot crops of following dependent of dead military hero: Oryza, Zea, Triticum, Hordeum, Avena, Secale, jowar belongs to, Panicum, saccharum, Ananas, Asparagus and allium.
Yet the application of active compound of the present invention never is limited to these genus, and also can extend to other plant in an identical manner.
Depend on compound concentrations, the compound natural disposition controlling weeds that is suitable for going out, for example industrial region and railway line, and the road and the square that have or do not have the plantation woods.Equally, compound can be used for preventing and treating the weeds of perennial crop, for example the weeds in forest, the decoration woods, orchard, vineyard, citrus woods, nut garden, any of several broadleaf plants plantation, cafetal, tea place, rubber plantation, oil palm plantation, cocoa plantation, mushy fruit woods and hops field, grassland, stadium and the pasture.And The compounds of this invention can also be used for optionally preventing and treating the weeds of annual crop.
Formula of the present invention (I) compound is particularly suitable for optionally preventing and treating unifacial leaf and broadleaf weed in unifacial leaf and the dicotyledonous crops in two kinds of modes before the bud and behind the bud.
Active compound can change into conventional preparation, as solution, emulsion, wettable powder, suspension agent, pulvis, the agent of dusting, paste, soluble powder, granule, suspended emulsion agent, with the natural or synthetic materials of active compound dipping, and wrap in micro-fine capsule in the polymkeric substance.
These preparations can be produced in a known manner, for example, with active compound and weighting agent, i.e. liquid and/or mix, and optional tensio-active agent, i.e. emulsifying agent and/or dispersion agent and/or the pore forming material of using with solid carrier.
Using water as under the situation of weighting agent, also can make solubility promoter with organic solvent.The liquid solvent that is fit to mainly contains: aromatic substance, and as dimethylbenzene, toluene or alkylnaphthalene, chloro aromatic substance and chlorinated aliphatic hydrocarbon are as chlorinated benzene class, polyvinyl chloride-base or methylene dichloride, aliphatic hydrocrbon, as hexanaphthene or paraffin, for example oil gold-plating part, mineral and vegetables oil, alcohols, as butanols or glycol with and ether and ester, ketone, as acetone, methylethylketone, methyl iso-butyl ketone (MIBK) or pimelinketone, intensive polar solvent is as dimethyl formamide or dimethyl sulfoxide (DMSO) and water.
The solid carrier that is fit to is: for example ammonium salt and ground natural mineral matter, as kaolin, clay, talcum, chalk, quartz, attapulgite, montmorillonite or diatomite, with ground synthetic mineral matter, as high dispersive silicon-dioxide, alumina and silicate, the solid carrier that is suitable for granule has: for example crush and fractionated natural mineral matter such as calcite, marble, float stone, sepiolite and rhombspar, and the synthetic particle of organic and inorganic powder and following organic particle: wood sawdust, coconut husk, corn cob and tobacco stem; The emulsifying agent and/or the pore forming material that are fit to are: for example nonionic and anionic emulsifier, as polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, for example, the alkaryl polyglycol ether, alkylsulfonate, alkyl-sulphate, arylsulphonate and albumin hydrolysate; The dispersion agent that is fit to is: for example, and lignin sulfite waste liquor and methylcellulose gum.
Can use the carboxymethyl cellulose and the natural and synthetic polymer of tackiness agent such as powdery, particle or latex form in the preparation, as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipid, as kephalin and Yelkin TTS, and synthetic phospholipid.Other tackiness agent can be mineral oil and vegetables oil.
Also may use tinting material, as mineral dye, for example ferric oxide, titanium oxide and Prussian blue, and organic dye are as the salt of alizarine dyestuff, azoic dyestuff and metal phthalocyanine dyestuff and micronutrient element such as iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Usually contain 0.1 to 95% active compound by weight in the preparation, preferred 0.5 to 90%
Be controlling weeds, active compound of the present invention, its former state or with its dosage form also can be used as the mixture with known weedicide, whole preparation or the possible mixed thing of bucket and uses.
The possible common component of mixture is known weedicide, for example, acetochlor, acifluorfen (sodium salt), aclonifen, alachlor, alloxydim (sodium salt), ametryn, amidochlor, the acyl ethyl methyl, the spirit of sulphur grass, atrazine, the tetrazolium ethyl methyl, benazolin, benfuresate, benzyl ethyl methyl (methyl esters), bentazone, benzofenap, benzoylpropethyl (ethyl ester), two alanyl phosphorus, bifenox, bromobutide, bromofenoxim, bromoxynil, Butachlor technical 92, the fourth grass is special, cafenstro1e, block careless amine, chlomethoxyfen, weed eradication is flat, pyrazon, chlorimuron (ethyl ester), chlornitrofen, chlorsulfuron, chlorotoluron, cinmethylin, ether is yellow grand, clethodim, alkynes oxalic acid, clomazone, difluoro pyridine acid, clopyrasulfuron (methyl), cloransulam (methyl), cumyluron, cyanazine, the weed eradication spy, AC322140, cycloxydim, cyhalofop-butyl, 2,4-drips, 2, the 4-Embutox, 2,4-drips propionic acid, desmedipham, di_allate, dicamba 98, diclofop-methyl (methyl esters), two benzene azoles are fast, diflufenican, fourth is disliked grand, dimepiperate, dimethachlor, diformazan third second is clean, dimethenamid, the spirit of amino second fluorine, diphenamide, diquat, dithiopyr, Diuron Tech, daimuron, EPTC, esprocarb, ethalfluralin, Ethanetsulfuron (methyl esters), ethofumesate, ethoxyfen, etobenzanid, the fenoxaprop-P ethyl ester, wheat straw volt (isopropyl ester), the wheat straw volt (isopropyl ester-L), wheat straw volt (methyl esters), the pyridine ethyl methyl, fluazifop (butyl ester), flumetsulam, methylarsonic acid, flumioxazin, flumipropyn, fluometuron, the fluorine cisanilide, fluoroglycofenethyl (ethyl ester), amine grass azoles, flupropacil, the fluorenes butyric acid, the fluorine butanone, fluroxypyr, flurprimidol, flurtamone, Fomesafen, Glufosinate (ammonium salt), glyphosate (isopropyl ammonium salt), halosafen, pyrrole fluorine chlorine standing grain spirit (ethoxy ethyl ester), hexazinone, miaow grass ester (methyl esters), imazamethapyr, imazamox, the weed eradication cigarette, the weed eradication quinoline, Imazethapyr, imidazoles is yellow grand, ioxynil, isopropalin, isoproturon, different evil acyl grass, isoxaflutole, dislike careless ether, lactofen, lenacil, methoxydiuron, 2 first, 4 chlorine, Vi par, mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metsulfuron-methyl (methyl esters), the piperazine humulone, Hydram, monolinuron, naproanilide, napropamide, neburon, nicoculsfuron, norflurazon, orbencarb, oryzalin, oxadiazon, oxyfluorfen, Paraquat, pendimethalin, phenmedipham, piperophos, the third careless amine, Fluoropyrimidinesulfuron (methyl esters), prometryn, propachlor, Stam F-34, propaquizafop, pentyne grass amine, prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron (ethyl ester), pyrazoxyfen, pyributicarb, pyridate, pyrithiobacsodium, quinclorac, quinmerac, quizalofop (ethyl ester), quizalofop (tetrahydrochysene chaff ester), the sulfone ethyl methyl, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, ethyl methyl (methyl esters), grass sulphur phosphorus, tebutam, terbufos benzthiazuron, terbuthylazine, terbutryn, P DimethenamidP, thifluzamide, thrizopyr, thidiazimin, thiophene methyl (methyl esters), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron-methyl (methyl esters), TRICLOPYR ACID, tridiphane, trifluralin and fluorine amine are yellow grand.
It also can be mixture with other known activity compound such as mycocide, sterilant, miticide, nematocides, bird repellent, plant food and soil conditioner.
Active compound can with itself, with its preparation or by further dilution and the type of service of preparation uses of warp, as direct available solution, suspension, emulsion, pulvis, paste and granule.They use with ordinary method, for example pour, spraying, atomizing or spread fertilizer over the fields or the like.
Active compound of the present invention can be used before or after plant germination.They also can mix in the soil prior to seeding.
The amount of used active compound can change in quite wide scope.Consumption depends on required effect basically.Usually, usage quantity is between per hectare soil surface-area restrains to 10 kilograms with 1, and preferred per hectare 5 grams are to 5 kilograms.
The preparation of active compound of the present invention and use can be referring to the following example.Preparation embodiment: embodiment 1 (method (a))
Under room temperature (about 20 ℃), 3.0g (25mmol) l-(3-trifluoromethyl-phenoxymethyl)-propyl chloride manthanoate (racemic modification) is under agitation joined 2.5g (10mmol) 2, in the solution of 3-dimethyl-aniline in 80ml toluene, and reaction mixture at room temperature stirred 15 hours.This mixture is water and 1N salt acid elution subsequently, with dried over sodium sulfate and filtration.Solvent carefully distills under pump vacuum.
Provide O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group of 3.5g (theoretical value 92%) thus] N-(2,3-dimethyl-phenyl)-carbamate (racemic modification), a kind of crystal residue, 76 ℃ of fusing points.
By the method for embodiment 1 and the general description of method produced according to the present invention, also can prepare formula (I) compound of for example listing in the table 1 hereinafter.
Figure A9881037800272
In all cases, they all are racemic modifications.R 1Position-if desired-expression CF 3Under each situation on 3.Structure is passed through 1H NMR composes confirmation.Table 1: formula (I) examples for compounds
Embodiment ?m (position) R 1 ??R 2 ?R 3 (position) (R 4) n Fusing point (℃)
?2 ?0 - ?C 2H 5 ?CH 3 (4)CH 3 ?58
?3 ?0 - ?C 2H 5 ?CH 3 (5)CH 3 ?102
?4 ?0 - ?C 2H 5 ?CH 3 (6)CH 3 ?61
?5 ?0 - ?C 2H 5 ?CH 3 (4，5)(CH 3) 2 ?-
?6 ?0 - ?C 2H 5 ?CH 3 (3，5)(CH 3) 2 ?-
?7 ?0 - ?C 2H 5 ?CH 3 (3)Br ?-
?8 ?0 - ?C 2H 5 ?CH 3 (4)Br ?-
?9 ?0 - ?C 2H 5 ?CH 3 (5)Br ?-
?10 ?0 - ?C 2H 5 ?CH 3 (3)CN ?-
?11 ?0 - ?C 2H 5 ?CH 3 (4)CN ?-
?12 ?0 - ?C 2H 5 ?CH 3 (5)CN ?-
?13 ?0 - ?C 2H 5 ?CH 3 (5)CF 3 ?-
?14 ?0 - ?C 2H 5 ?CH 3 (3)OCH 3 ?-
?15 ?0 - ?C 2H 5 ?CH 3 (4)OCH 3 (unformed)
?16 ?0 - ?C 2H 5 ?CH 3 (5)OCH 3 (unformed)
?17 ?0 - ?C 2H 5 ?CH 3 (3)COOC 2H 5 ?-
?18 ?0 - ?C 2H 5 ?CH 3 (4)COOC 2H 5 ?-
?19 ?0 - ?C 2H 5 ?CH 3 (5)COOC 2H 5 ?-
?20 ?0 - ?C 2H 5 ?F (3)CH 3 ?-
?21 ?0 - ?C 2H 5 ?F (4)CH 3 (unformed)
?22 ?0 - ?C 2H 5 ?F (5)CH 3 (unformed)
?23 ?0 - ?C 2H 5 ?F (6)CH 3 ?-
?24 ?0 - ?C 2H 5 ?F (4)Br ?-
?25 ?0 - ?C 2H 5 ?F (3)CF 3 ?-
?26 ?0 - ?C 2H 5 ?F (4)CF 3 ?-
?27 ?0 - ?C 2H5 ?F (5)CF 3 ?-
?28 ?0 - ?C 2H 5 ?F (6)CF 3 ?-
?29 ?0 - ?C 2H 5 ?F (5)OCH 3(6)CH 3 ?-
Embodiment ?m (position) R 1 ?R 2 ?R 3 (position) (R 4) n Fusing point (℃)
30 ?0 - ?C 2H 5 ?F (3)OCH 3 -
31 ?0 - ?C 2H 5 ?F (4)OCH 3 -
32 ?0 - ?C 2H 5 ?F (6)OCH 3 -
33 ?0 - ?C 2H 5 ?CF 3 (6)Br -
34 ?0 - ?C 2H 5 ?CF 3 (4)OCH 3 -
35 ?0 - ?C 2H 5 ?CF 3 (4)Br -
36 ?0 - ?C 2H 5 ?CF 3 (4)CN -
37 ?0 - ?C 2H 5 ?CF 3 (4)CF 3 -
38 ?0 - ?C 2H 5 ?CF 3 (5)CF 3 -
39 ?0 - ?C 2H 5 ?CF 3 (6)CF 3 -
40 ?0 - ?C 2H 5 ?OCH 3 (3)CH 3 -
41 ?0 - ?C 2H 5 ?OCH 3 (4)CH 3 -
42 ?0 - ?C 2H 5 ?OCH 3 (5)CH 3 -
43 ?0 - ?C 2H 5 ?OCH 3 (5)COOC 2H 5 -
44 ?0 - ?C 2H 5 ?CN (3)CH 3 -
45 ?0 - ?C 2H 5 ?CN (4)CH 3 -
46 ?0 - ?C 2H 5 ?CN (5)CH 3 -
47 ?0 - ?C 2H 5 ?COOC 2H 5 (3)CH 3 -
48 ?0 - ?C 2H 5 ?COOC 2H 5 (4)CH 3 -
49 ?0 - ?C 2H 5 ?COOC 2H 5 (5)CH 3 -
50 ?0 - ?C 2H 5 ?Br (3)CH 3 -
51 ?0 - ?C 2H 5 ?Br (4)CH 3 -
52 ?0 - ?C 2H 5 ?Br (5)CH 3 -
53 ?0 - ?C 2H 5 ?Br (6)CH 3 -
54 ?0 - ?C 2H 5 ?Br (4)CH 3 -
55 ?0 - ?C 2H 5 ?OCH 3 (4-)OCH 3 (unformed)
56 ?0 - ?C 2H 5 ?CH 3 (6-)C 2H 5 (unformed)
57 ?0 - ?C 2H 5 ?OCH 3 (5-)OCH 3 (unformed)
58 ?0 - ?C 2H 5 ?OCH 3 (3-)OCH 3 (unformed)
Embodiment m (position) R 1 ?R 2 R 3 (position) (R 4) n Fusing point (℃)
59 ?0 - ?CH 3 ?CH 3 (4-)CH 3 (unformed)
60 ?0 - ?CH 3 ?CH 3 (5-)CH 3 (unformed)
61 ?0 - ?CH 3 ?CH 3 (4-)OCH 3 (unformed)
62 ?0 - ?CH 3 ?OCH 3 (5-)OCH 3 (unformed)
63 ?0 - ?CH 3 ?OCH 3 (3-)OCH 3 (unformed)
64 ?0 (6-)F ?C 2H 5 ?CH 3 (3-)CH 3 (unformed)
65 ?0 (6-)F ?C 2H 5 ?CF 3 - (unformed)
66 ?0 (2-)F ?C 2H 5 ?CH 3 (3-)CH 3 (unformed)
67 ?0 (2-)F ?C 2H 5 ?Cl (3-)Cl (unformed)
68 ?0 (2-)F ?C 2H 5 ?CF 3 - (unformed)
69 ?0 (2-)F ?C 2H 5 ?Cl (3-)Cl (n D 20＝1.5263)
70 ?0 (2-)F ?C 2H 5 ?CH 3 (3-)CH 3 (unformed)
71 ?0 (4-)F ?C 2H 5 ?CF 3 - (n D 20＝1.4842)
72 ?0 (4-)F ?C 2H 5 ?CH 3 (4-)F (unformed)
73 ?0 (4-)C1 ?C 2H 5 ?CH 3 (3-)CH 3 (unformed)
74 ?0 (4-)Cl ?C 2H 5 ?CH 3 (4-)F ?76℃
75 ?0 (5-)CF 3 ?C 2H 5 ?CH 3 (4-)F ?113℃
76 ?0 (5-)CF 3 ?C 2H 5 ?CH 3 (3-)CH 3 ?140℃
77 ?0 - ?C 4H 9-n ?CH 3 (3-)CH 3 ?92℃
78 ?0 (4-)F ?C 2H 5 ?F (4-)F ?40℃
79 ?0 (4-)F ?C 3H 7-n ?F (4-)F ?71℃
80 ?0 (4-)F ?C 3H 7-n Cl (3-)Cl ?81℃
81 ?0 (4-)F ?C 3H 7-n CH 3 (3-)CH 3 ?73℃
82 ?0 (6-)F ?C 2H 5 ?F (4-)F (n D 20＝1.4876)
83 ?0 (2-)F ?C 2H 5 ?F (4-)F (n D 20＝1.4874)
84 ?0 (5-)CF 3 ?C 2H 5 ?CF 3 - (unformed)
85 ?0 - ?CH 3 ?F (5-)CH 3 (unformed)
86 ?0 - ?CH 3 ?CH 3 (5-)OCH 3 (unformed)
87 ?0 - ?CH 3 ?F (4-)CH 3 (unformed)
Test solvent before the Application Example embodiment A bud: 5 parts of weight acetone emulsifying agents: the alkaryl polyglycol ether of 1 part of weight
When preparing the active agent preparations that is fit to, with the active compound of 1 part of weight and the solvent of described amount, with the emulsifying agent adding of described amount, and water is diluted to desired concn with this missible oil.
The seed of test plant is broadcast in the common soil, and after about 24 hours, soil waters with active agent preparations, uses the activeconstituents of specified quantitative on per unit area.Select the concentration of spraying fluid, the specified quantitative of required active compound is used with the spray amount of 1000 premium on currency/hectares.
After three weeks, the degree of damage of plant and the developmental phase of untreated control are compared, infringement % is made in range estimation.
The content of numerical value is as follows:
0%=do not have effect (be untreated identical)
100%=damages fully
In this test, preparation embodiment 1,2,3 and 4 pairs of weeds demonstrate strong activity, and they some can be tolerated well by crop such as corn, barley and soybean.Test solvent behind the Embodiment B bud: 5 parts of weight acetone emulsifying agents: the alkaryl polyglycol ether of 1 part of weight
When preparing the active agent preparations that is fit to, with the active compound of 1 part of weight and the solvent of described amount, with the emulsifying agent adding of described amount, and water is diluted to desired concn with this missible oil.
Press a certain amount of required active agent preparations of unit surface spray application to plant height 5-15 centimetre test plant.Select the concentration of spraying fluid, the specified quantitative of required compound is used with the amount of 1,000 premium on currency/hectare.
After three weeks, the degree of damage of plant is compared with untreated control, make infringement %.
The connotation of numerical value is as follows:
0%=do not have effect (be untreated identical)
The 100%=completely destroy
In this test, preparation embodiment 1,2 and 4 pairs of weeds demonstrate strong activity, and they some can be tolerated well by crop such as corn.

Claims (6)

1. the O-aryloxy alkyl N-aryl-carbamate of the replacement of general formula (I),
Figure A9881037800021
Wherein
M represents numeral 0,1 or 2,
N represents numeral 0,1,2,3 or 4, and its prerequisite is, under each situation, m and n sum are at least 1,
R 1Represent cyano group, halogen or all can choose wantonly by cyano group-, halogen-or C 1-C 4The alkyl or the alkoxyl group that respectively have 1 to 4 carbon atom of-alkoxyl group-replacement,
R 2Representative optional by cyano group-, halogen-or C 1-C 4The alkyl with 1 to 4 carbon atom of-alkoxyl group-replacement,
R 3Represent cyano group, fluorine, bromine, iodine or all can choose wantonly by cyano group-, halogen-or C 1-C 4The alkyl, alkoxyl group or the alkoxy carbonyl that respectively have 1 to 4 carbon atom of-alkoxyl group-replacement, and-
M represent under 1 or 2 the situation-also represent chlorine and
R 4Represent cyano group, bromine, iodine or all can choose wantonly by cyano group-, halogen-or C 1-C 4The alkyl, alkoxyl group or the alkoxy carbonyl that respectively have 1 to 4 carbon atom of-alkoxyl group-replacement, and-represent under 1 or 2 the situation-also represent fluorine or chlorine at m,
Compound O-[1-(3-trifluoromethyl-phenoxymethyl) propyl group] except N-(2-methoxyl group 5-methyl-phenyl)-carbamate.
2. the O-aryloxy alkyl N-aryl-carbamate of the replacement of the general formula of claim 1 (I),
It is characterized in that,
M represents numeral 0,1 or 2,
N represents numeral 0,1,2 or 3, and its prerequisite is, under each situation, m and n sum are at least 1,
R 1Represent cyano group, fluorine, chlorine, bromine or all can choose wantonly by cyano group-, fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or isopropoxy,
R 2Representative all can choose wantonly by cyano group-, the methyl of fluoro-, chloro-, methoxy or ethoxy-replacements, ethyl, just-or sec.-propyl, just-, different-, the second month in a season-or the tertiary butyl,
R 3Represent cyano group, fluorine, bromine, iodine or all can choose wantonly by cyano group-, fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or isopropoxy, methoxycarbonyl, ethoxy carbonyl, just-or different-propoxycarbonyl, and-represent at m under 1 or 2 the situation-also represent chlorine and
R 4Represent cyano group, bromine, iodine or all can choose wantonly by cyano group-, fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, just-, different-, secondary-or the tertiary butyl, methoxyl group, oxyethyl group, just-or isopropoxy, just-, different-, secondary-or tert.-butoxy, methoxycarbonyl, ethoxy carbonyl, just-or different-propoxycarbonyl, and-represent under 1 or 2 the situation-also represent fluorine or chlorine at m
Compound O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] except N-(2-methoxyl group 5-methyl-phenyl)-carbamate.
3. the O-aryloxy alkyl N-aryl-carbamate of the replacement of the general formula of claim 1 (I),
It is characterized in that,
M represents numeral 0 or 1,
N represents numeral 0,1 or 2, and its prerequisite is, under each situation, m and n sum are at least 1,
R 1Represent cyano group, fluorine, chlorine, bromine or all can choose methyl, ethyl, the methoxy or ethoxy that replaces by fluoro-or chloro-wantonly,
R 2Representative all can choose wantonly by fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or sec.-propyl,
R 3Represent cyano group, fluorine, bromine or all can choose wantonly by fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, methoxyl group, oxyethyl group, just-or isopropoxy, methoxycarbonyl, ethoxy carbonyl, just-or different-propoxycarbonyl, and-represent at m under 1 the situation-also represent chlorine and
R 4Represent cyano group, bromine, iodine or all can choose wantonly by fluoro-, chloro-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just-or different-propyl group, methoxyl group, oxyethyl group, just-or isopropoxy, methoxycarbonyl, ethoxy carbonyl, just-or different-propoxycarbonyl, and-represent under 1 the situation-also represent fluorine or chlorine at m
Compound O-[1-(3-trifluoromethyl-phenoxymethyl)-propyl group] except N-(2-methoxyl group 5-methyl-phenyl)-carbamate.
4. the following acquisition of O-aryloxy alkyl N-aryl-carbamate of the replacement of the general formula of claim 1 to 3 (I):
(a) if, make the arylamines reaction of the chloroformic acid aryloxy alkyl ester and the general formula (III) of general formula (II) if suit reacting in the presence of the auxiliary and suiting in the presence of thinner
Figure A9881037800041
Wherein
M, R 1And R 2The as above definition of claim 1 to 3,
Figure A9881037800042
N, R 3And R 4As above claim 1 to 3 definition,
Or
(b) if, make the aryl isocyanate reaction of the aryloxy alkanol and the logical formula V of general formula (IV) if suit reacting in the presence of the auxiliary and suiting in the presence of thinner
Figure A9881037800043
Wherein
M, R 1And R 2As above claim 1 to 3 definition,
N, R 3And R 4Such as claim 1 to 3 definition.
5. the application of the O-aryloxy alkyl N-aryl of at least a replacement of claim 1 to 3-carbamate control noxious plant.
6. herbicidal composition is characterized in that, they comprise at least a according to claim 1 to 3 the O-aryloxy alkyl N-aryl-carbamate of replacement.
CN 98810378 1997-10-20 1998-10-07 Substd. N-aryl-O-aryloxyalkyl carbamates and their use as herbicides Pending CN1276787A (en)

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