WO1991019694A1 - Isomere optique de la forme r d'un derive d'ether de diphenyle, et herbicide le contenant a titre d'ingredient actif - Google Patents
Isomere optique de la forme r d'un derive d'ether de diphenyle, et herbicide le contenant a titre d'ingredient actif Download PDFInfo
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- WO1991019694A1 WO1991019694A1 PCT/JP1991/000714 JP9100714W WO9119694A1 WO 1991019694 A1 WO1991019694 A1 WO 1991019694A1 JP 9100714 W JP9100714 W JP 9100714W WO 9119694 A1 WO9119694 A1 WO 9119694A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
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- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
Definitions
- the present invention is directed to the R optical isomer of a diphenyl ether derivative and a herbicide containing the same as an active ingredient. More specifically, the present invention exhibits excellent herbicidal activity against broad-leaved weeds and fine-leaved weeds, and has selective herbicidal activity without substantially impairing the growth of crops depending on the method of use, treatment method and treatment amount. It is a fight against herbicides.
- 2,4-dichlorophenoxyacetic acid types of herbicides that selectively kill broadleaf weeds, such as 2,4-dichlorophenoxyacetic acid, have been known as selective herbicidally active compounds.
- the selective herbicidal activity of 2,4 diclo-mouth phenoxyacetic acid is a selective herbicidal activity between leaf plants, including crop plants and weeds, and broadleaf plants, also including crop plants and weeds. It is known that 2,4-chloroacetic acid phenoxyacetic acid has extremely low or no activity on narrow-leaved plants. (See, for example, Nature, Vol. 155, pp. 498 (1945)).
- a compound having an aromatic group such as a chloro or trifluoromethyl-substituted phenoxy group or a compound having a chloro or trifluoromethyl-substituted pyridyloxy group or the like is selected from narrow plants. It is also known that they have an active killing activity (U.S. Pat. Nos. 4,270,948, 4,309,562, 314,06, 4,332,961 and 3,954). , 442, JP-A-52-125626, JP-A-52-15825 and British Patent 1,579, 201. However, these compounds are also useful for producing useful crops such as rice or corn. To die.
- Herbicides containing certain ⁇ ⁇ -phosphonomethyldaricin derivatives as the main active ingredient are also known and commercially available.
- This ⁇ -phosphonomethyldaricin derivative is basically a non-selective herbicide. However, at low doses, it can be used for herbicides against perennial weeds such as hamazuge in the family Calidae and broadleaf weeds such as akaza and aobu. Activity is reduced.
- N-phosphonomethyldaricin derivatives are slow-acting and are not suitable for quickly removing weeds on agricultural or non-agricultural lands and performing the following operations. For example, in arable land, it is necessary to kill all weeds before sowing the crop, but in the case of slow-acting crops, delays in sowing the crop or harm to the seed of the crop may be considered.
- N-phosphonomethylglycine derivatives are considered as low-dose, fast-acting nonselective herbicides even in non-cultivated lands due to delays in building or railroad construction or road weeding. Insufficient.
- herbicides containing certain dalfosinate compounds as the main active ingredient are known and commercially available.
- This glufosinate compound is also basically a non-selective herbicide, but has a drawback that the herbicidal activity against broadleaf weeds such as akaza, aobu and ichibi is reduced at a low dose.
- R 1 is an alkyl group having 1 to 5 carbon atoms or a phenyl group.
- R 2 is a hydroxy group, an alkyl group having 1 to 5 carbon atoms which may be substituted by a halogen atom, a phenyl group which may be substituted by a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and a carbon atom having 1 to 5 carbon atoms.
- j c represents an asymmetric carbon atom.
- a herbicide composition containing the compound as a main active ingredient, which is an R optical isomer of a diphenyl ether derivative represented by or a salt thereof.
- X and Y are the same or different and are each a hydrogen atom, a halogen atom, a CF 3 , or an alkyl group having 1 to 5 carbon atoms.
- the halogen atom is, for example, fluorine, chlorine or bromine.
- the alkyl group having 1 to 5 carbon atoms may be linear or branched, for example, methyl, ethyl, n-a-pyr, is. N-butyl, sec-butyl, iso-butyl, t-butyl, n-pentyl, etc.
- X and Y are the same or different, each preferably chlorine or a CF 3.
- R 2 is a hydroxy group, an alkyl group having 1 to 5 carbon atoms which may be substituted by a halogen atom, a phenyl group which may be substituted by a halogen atom, An alkoxy group, an alkenyloxy group having 1 to 5 carbon atoms or (where R 3 and R 4 are hydrogen atoms or 1 to 5 carbon atoms) Which is an alkyl group of Examples of the halogen atom and the alkyl group having 1 to 5 carbon atoms include the same as those described in the definition of X and Y.
- the alkoxy groups (5) to (5) may be linear or branched, for example, methoxy, ethoxy, 1-broxy, is0-f. L-oxy, n-butoxy, sec-butoxy, t-butoxy, n-pentaloxy, etc .: Examples of the alkenyloxy group having a prime number of 1 to 5 include ethenoxy, propenoxy, butenoxy, pentenoxy, etc. You.
- R optical isomer of the diphenyl ether derivative of the above formula (I) for example, the R optical isomer of the following compound can be exemplified.
- the compound of the above formula (I) can be produced, for example, by the following reaction method, but is not limited thereto.
- an alkaline earth metal salt may be present, for example, sodium formate, potassium formate, calcium formate, magnesium formate, sodium acetate, potassium acetate, calcium sulfate, magnesium acetate, and the like.
- inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and pyridine triethylamine are used.
- Organic bases such as tolylenediamine and benzyltrimethylammonium hydroxide may be used, with or without a solvent, and depending on the reaction conditions used, organic fatty acids such as formic acid and acetic acid, benzene, toluene, Xylene Aromatic hydrocarbons such as ethyl acetate, tetrahydrofuran, dioxane, ethyl ether, acetone, methyl ethyl ketone, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone, and pyridine can also be used. When a solvent having low compatibility with water is used, it can be used in a two-phase system.
- the reaction is carried out in the range of O to 20 G ° C, but preferably in the range of 30 to 150.
- the reaction is often performed at the boiling point.
- examples of ⁇ ⁇ ⁇ ⁇ include alkali metals, alkaline earth metals, copper, and zinc.
- W include a halogen atom, and chlorine and bromine are particularly preferable.
- the reaction temperature is usually O ⁇ 1 5 0 ° C, about room temperature ⁇ 1 0 0 e C is preferred.
- a halogen such as bromine or iodine, lead tetraacetate or copper chloride is used.
- an ammine cobalt complex is also used as the oxidizing agent.
- a base may be used, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate may be used. Examples thereof include allylic cholate such as lium methoxide, sodium ethoxide, and potassium tert-butoxide. Reaction temperature o-ioo. c, preferably in the range of ⁇ to ⁇ c.
- the R optical isomer of the diphenyl ether derivative of the above formula (e) of the present invention affects the metabolism of plants, for example, suppresses the growth of certain plants, regulates the growth of certain plants, and controls the growth of certain plants. It has the property of dwarfing some plants or dying certain plants.
- the compound of the above formula (I) of the present invention can be applied to plant seeds, and can also be applied to plants at various stages of growth via foliage or roots. That is, the compound of the present invention, as it is or in the form of a composition, is a plant whose growth is to be inhibited, that is, a plant whose metabolism is to be regulated, a seed of such a plant, or a plant in which such a plant is growing. Applied in a location or where such a plant is expected to grow, in an amount sufficient to regulate plant metabolism.
- the compounds of the invention can regulate the metabolism of plants, for example in an amount of 0.001 to 20 kgZha, more preferably in an amount of 0.005 to 10 kgZ, particularly preferably in an amount of 0.005 to 5 kg / 'ha. It can be used in usual forms such as solutions, emulsions, suspensions, powders, pastes and granules. Such preparations include, for example, solid carriers such as talc, bentoite, clay, phosphorus, kieselguhr, diatomaceous earth, white potato, vermicinilite, slaked lime, ammonium sulfate, urea, etc .; water, alcohol, dioxane.
- Liquid carriers Alkyl sulfate, Alkyl Surfactants such as sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ether, polyoxyethylene rubbitan monoalkylate, and dinaphthylmethane disulfonate; emulsifiers or dispersants; carboxymethylcellulose, arabic One or prepared using two or more various additives such as an equal - to be.
- Such a preparation can be prepared, for example, by mixing the compound with the above carrier and Z or an emulsifier.
- the compounds of the invention can be present in the formulations usually in a proportion of from 0.1 to 1% by weight, preferably from 0.1 to 1% by weight.
- the compounds of the present invention may be applied to the plant as such, or in admixture with other active compounds, or in the form of a formulation as described above, for example, in the usual manner, such as by spraying, spraying, dusting or dusting. be able to.
- the compound of the present invention suppresses the growth or control of harmful plants.
- the purpose of the present invention is to remove the compound of the present invention as it is or in the form of a composition
- these plants are used in a place where the beneficial plant or its seed and the harmful plant or its seed coexist or are likely to coexist. It can be applied directly to the seed or to the soil in an amount sufficient to suppress or eliminate the growth of harmful plants.
- a harmful plant is generally a human-created environment, such as a plant that enters and breeds from the surrounding natural world in a field, is useless in that environment, or is perceived by humans to be harmful.
- Such harmful plants are generally referred to as weeds.
- the weeds include, for example, the following various weeds.
- the compound of the above formula ⁇ I> has substantially no phytotoxicity to useful crops, especially soybeans and corn, depending on the method of use, treatment method and amount of treatment, and therefore, substantially no growth of these compounds is possible.
- the compound of the present invention or a composition containing the compound of the present invention can not only kill or inhibit the growth of a weed to be herbicidally but also germinate by spraying the foliage on the foliage. By applying it to soil beforehand, it can be used as a selective herbicide that does not substantially inhibit germination and growth of useful crops and can suppress germination and growth of weeds.
- the compounds of the general formula (I) according to the invention can be used together with various herbicide compounds known per se, whereby the compounds of the formula (I) according to the invention are effective against broad-leaved and fine-leaved weeds.
- used together with other compounds that show excellent herbicidal activity against, for example, fine-leaved weeds, so that they can exert their full herbicidal activity, and thus are effective against both broad-leaved and fine-leaved weeds A herbicidal composition can be provided.
- R 21 and R 22 are the same or different and are each; — 0 H or 1 ⁇ R 24 and R 2 — ⁇ H,
- R 24 is an alkyl group with 1 to 5 carbon atoms, a cyclohexyl group, and a carbon number! I haloalkyl group of 1 to 5, alkenyl of 2 to 5 carbon atoms
- R 25 and R 26 are the same or different Resona respectively hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, also R 25 And R 26 together with the nitrogen atom to which they are attached can form a morpholino, piberidino or pyrrolidino group.
- N-phosphonomethyldaricin derivative represented by the formula: and Z or the following formula (V)
- R 31 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
- R 32 is —OH, —NH 2 , —NHN 3 ⁇ 4, is _ number 1-12 alkoxyl group
- R 21 and R 22 are the same or different and each is 1 OH or —OR 24
- R 23 is 1 OH, 1 OR 24 or 1 NR 25 R 26
- R 24 is an alkyl group having 1 to 5 carbon atoms, a cyclohexyl group, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group or an alkoxyalkyl group having 2 to 5 carbon atoms, a haloalkoxyalkyl group, or an alkoxyalkoxy group.
- Alkyl groups (where each alkoxy, haloalkoxy and alkyl has 1 to 5 carbon atoms) and phenyl groups.
- R 25 and R 26 are the same or different and are a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group having 1 to 5 carbon atoms, and an alkenyl group having 2 to 5 carbon atoms, and R 25 and R 26 are Can form a morpholino, piperidino or pyrrolidino group with the nitrogen atom to which they are attached
- R 24 , R 25 and R 26 are the same as those described above for X and Y in the formula (I).
- R 24 is a haloalkyl group having 1 to carbon atoms, for example Nono Romechiru, Haroechiru, Gino ⁇ Roechiru, Nono port propyl, halobutyl, Bruno, halogen atom can be exemplified mouth pentyl, for example off ,, / Element, chlorine, bromine.
- Examples of the alkenyl group having 2 to 5 carbon atoms for R 24 , R 25 and R 26 include vinyl, aropenyl, butenyl and pentenyl.
- alkoxyalkyl group for R 24 examples include, for example, methoxethyl, ethoxyxyl and the like.
- haloalkoxyalkyl group for R 24 for example, chloromethoxethyl, chloromethoxyl can be mentioned as preferred.
- alkoxyalkoxyalkyl group for R 24 for example, methoxetoxyethyl or ethoxyxethoxyethyl can be mentioned as preferred.
- hydroxy ⁇ alkyl group of 1 to 5 carbon atoms for R 25 and R 26, for example hydroxymethyl, hydroxy Shechiru can ani gel as preferred hydroxy pentyl.
- the compound of the above formula (IV) is, in the composition of the present invention, It can also be used as an acid addition salt or a salt with a base.
- an acid for forming an acid addition salt for example, a strong acid having a pKa of not more than 2.
- acids include hydrochloric acid, sulfuric acid, phosphoric acid, trifluoroacetic acid, trichloroacetic acid and the like.
- Salts with bases are, above formula (W>, when R 2 1, R 2 2 Contact and one or both the less of R 2 3 representing a - ⁇ H, for example their alkali metal, alkaline earth metal , Copper, ammonium or organic ammonium or trimethylsulfonium, triethylsulfonium, tripropylsulfonium, trimethylsulfoxonium, triethylsulfoxonium, tripropylsulfoxom It is formed as a salt with a cation such as dimethyl.
- Alkali metal refers to, for example, lithium, sodium or potassium
- alkaline earth metal refers to, for example, magnesium or calcium
- Organic ammonium salts are prepared from low molecular weight organic amines, such as those having a molecular weight of about 300 or less.
- organic amines include, for example, alkylamines, alkylenepolyamines, and alkyneamines.
- Lamines such as methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, secondary monobutylamine, n-amylamine, Isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pendecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octactylamine, mectadecylamine.
- ⁇ -butylethanolamine Arylamine, ⁇ -butenyl-2-amine, ⁇ -benthenyl-2-amine, 2,3—dimethylbutenyl-1-amine, dipthenyl-2-amine, ⁇ — Xenil-2-amine and propyl Rangenamine, primary aryarylamine, for example, aniline, methoxaniline, ethoxydiamine, o, m, p-tonoleidine, phenylenediamine, 2, 4, 6—triplomoredine, benzidine, dephthylamine, o, m, p And heterocyclic amines such as pyridine, morpholine, piperidine, pyrrolidine, indoline, and azepine.
- primary aryarylamine for example, aniline, methoxaniline, ethoxydiamine, o, m, p-tonoleidine, phenylenediamine, 2, 4, 6—triplo
- R 21 , R 22 and R 23 are salts of one OH, —OH or
- R 21 , R 22 and R 23 are salts of 1 OH, and the remaining one of R 21 , R 22 and R 23 is 100 H
- the salts of 1 OH include, for example, ammonium or organic ammonium (here, the organic ammonium group is a monoalkyl ammonium, a dialkyl ammonium, a trialkyl ammonium, a monoalkenyl ammonium, a dialchem).
- the salt of the compound of the formula ⁇ IV> with the acid or base as described above is produced from the compound of the formula (IV) and the acid or base according to a method known per se.
- Examples of the compound of the above formula ((), an acid addition salt or a salt thereof with a base which are preferably used in the present invention are as follows.
- R 31 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
- R 32 is a carbon atom which may be substituted by —OH, —N3 ⁇ 4, —NHNH2, —NHCs3 ⁇ 4 or —OH. It is an alkoxyl group of numbers 1 to 12.
- alkyl group for R 31 examples include the alkyl groups having 1 to 4 carbon atoms among those described above for X and Y in the above formula (I).
- the alkoxy group of R 32 may be linear or branched, for example, methoxy, ethoxy, n-propoxy, is 0 —propoxy, ⁇ -butoxy, sec —butoxy, is 0 — ethoxy, tert-ethoxy, n-pentoxy, ii-Hexoxy, n-Heatoxy, n-Hetoxy, n-Nodecoxy, n-Decanoxy, n-Dedecanoxy and n-Dodecanoxy.
- These alkoxy groups may be substituted by a hydroxyl group (-OH): for example, hydroxyethoxy and the like.
- the compound represented by the above formula (V) can be used as an acid addition salt or a salt with a base in the composition of the present invention.
- Examples of the acid for forming the acid addition salt include the same acids as those exemplified for the acid addition salt of the formula (IV).
- the acid addition salt is believed to be formed at the primary amino group in formula (V).
- Examples of the base that forms a salt with the base include the same bases as those exemplified for the case of the formula (IV).
- R 31 is preferably a hydrogen atom, and more preferably R 3 ⁇ —OH, 1 N3 ⁇ 4, 1 N HN3 ⁇ 4, an alkoxylate having 1 to 4 carbon atoms, or a hydroxyalkoxy having 2 to 4 carbon atoms.
- Examples of the salt of the compound of the above formula (V ′) include, for example, Na, K, Cu, g, Ca, Za, Ni, Mn and Fe salts, ammonium salts, and the alkyl group having 1 carbon atom.
- ⁇ 4 Mono, Ji-ma Or salts with bases such as salts with trialkylamines or salts with aniline; or hydrochloric, sulfuric, hydrobromic, 1-II
- Acid addition salts of acids such as chloric acid or oxalic acid may be mentioned as preferred.
- the salt of the compound of the above formula (V) with the acid or base as described above is produced from the compound of the above formula (V) and the acid or base according to a method known per se.
- Examples of the compound of the above formula (V) preferably used in the present invention, or a salt with an acid addition salt or a base thereof are as follows.
- triazine herbicides can be used in combination with the general formula (I) of the present invention. It is also possible to use a mixture with a compound.
- the amount of the composition to be actually applied depends on a number of factors, such as the type of the particular target plant to be inhibited from growing, but is generally between 0, 01 and 10 kg gZ lia, preferably An amount of 0.05-5 kg g ha is suitable.
- a person skilled in the art can easily determine an appropriate use ratio and amount by standardized ordinary tests without particularly performing many experiments.
- the compound of the formula (I) of the present invention is a compound of the diphenyl ether derivative represented by the formula (I>)
- the compound of the optical isomer is also possible to contain the compound of the optical isomer to the S optical isomer in a ratio of 1 GG: ⁇ to 50:50 by weight.
- composition of the present invention can be applied in the form of a composition in which the active ingredient is mixed with a carrier comprising a solid or liquid diluent. Further, the composition may further contain an additive such as a surfactant. As such a diluent, carrier and surfactant, the same ones as described above can be used.
- composition of the present invention By containing the composition of the present invention together with a carrier and Z or a surfactant, it can be used as a usual-form preparation such as a solvent, an emulsion, a suspension, a powder or a paste.
- composition of the present invention may be prepared by combining the compound (e) with another herbicide compound and then mixing it with a carrier or the like to prepare a pharmaceutical preparation.
- the composition of the compound (I) and another herbicide may be used.
- the compound can be prepared by separately preparing a compound composition, adding a carrier and the like, if necessary, and mixing these compositions together to form a preparation.
- the compound (I) and the other herbicide compound are applied simultaneously or in an arbitrary order to a place where the weed is growing in an amount effective for killing the weed, the weed being obtained. It is a method of killing.
- the compound (I) and the other herbicide compound are the same as the compound (I) and the other herbicide compound.
- composition of compound (I) and the composition of other herbicide compounds can be applied to places where weeds grow over time. At that time, the compound
- composition (I) and the composition of the other herbicide compound may be any order.
- the time from the application of one of the compositions to the application of the other composition may be, for example, after the application of one of the compositions, the active compound (I) or the active compound (I) in the composition. It is preferable to apply the other composition to the roots of other herbicide compounds that remain on the surface of the weed, although it depends on the target plant, climatic conditions, etc., but usually within 2 to 3 days immediately after application of one. It is preferred to apply.
- the compound (I) and another herbicide compound before the crop emerges by applying the compound (I) and another herbicide compound before the crop emerges, the compound that grows in the place before the crop emerges can be obtained.
- the grass can wither, and the crop can grow smoothly.
- the application rates of the compound (e) and the other herbicide compounds can be appropriately determined based on the application rates described for the composition. According to the above method of the present invention, both broadleaf weeds and narrowleaf weeds can be killed advantageously with a low application rate.
- the compounds of the general formula (I) of the present invention can be used together with various insecticide compounds known per se.
- the invention's effect can be used together with various insecticide compounds known per se.
- the herbicidal activity is more excellent with a smaller amount of use than the racemic form. It is also possible to provide a herbicide, a diph X-nyiether derivative represented by the formula (I) and an N-phosphonomethylglycine derivative represented by the formula (IV) and / or a compound represented by the formula (v).
- Example 3 The compound was reacted with 0.58 part of the S optical isomer of o- (P-toluenesulfonyl) lactate in the same manner as in Example 1 to obtain 0.85 part of the desired compound.
- Example 3 The compound was reacted with 0.58 part of the S optical isomer of o- (P-toluenesulfonyl) lactate in the same manner as in Example 1 to obtain 0.85 part of the desired compound.
- Table 11 shows the nuclear magnetic resonance spectrum, infrared absorption spectrum and specific light intensity of the compound.
- Example 3 n-butanol was used in place of ethanol, and the reaction, post-treatment, and separation and purification were carried out in exactly the same manner to obtain 5.5 parts of the desired product.
- Table 11 shows the nuclear magnetic resonance spectrum, infrared absorption spectrum and specific light intensity of the compound.
- Table 11 shows the nuclear magnetic resonance spectrum, infrared absorption spectrum and specific light intensity of the compound.
- Example 1 o- (p-toluenesulfonyl) S optical isomer of lactate methyl ester In place of 7.8 parts, 5.0 parts of D.L-2-bromobromopropionate methyl ester was used, and the rest was exactly the same. Then, 10.5 parts of the desired product was obtained.
- Table 11 shows the nuclear magnetic resonance spectrum, infrared absorption spectrum and specific rotation of the compound.
- Example 1 the R optical isomer was used in place of the S optical isomer of o- (p-toluenesulfonyl) lactate methyl ester. 1. Five copies were obtained.
- the core of the compound Table 11 shows the magnetic resonance spectrum, infrared absorption spectrum and specific rotation.
- the diphenyl ethers shown in Table 2 were added to 5000 parts of a mixed solution of acetone and water (volume ratio 1: 1) so as to obtain a predetermined treatment amount, and a nonionic surfactant (trade name: SO) (Report 2680) 2.6 parts were added to prepare a solution.
- SO nonionic surfactant
- Plants were sown on soil and cultivated for 2-3 weeks after germination.
- Each of the diphenyl ethers and the N-phosphonomethyltilicin derivative shown in Table 3 was mixed at a predetermined mixing ratio and in a predetermined processing amount in a mixed solvent of water and acetone (volume ratio 1: 1, non-ionic Surfactant; trade name: S0RP0-2680 contained 0.05%> Dissolved in 16 parts by volume to prepare a spraying solution.
- Plants were cultivated in greenhouses for 2-3 weeks after germination by sowing or rhizome transplantation in plastic pots (diameter 10 cm) containing soil.
- the herbicidal activity was examined by applying the above-prepared solution to this plant so that the total applied volume was 4 ccZlOO.
- the method of Tammes [Tammes, PML: Neth J. Plant Path., Vol. 70, pp. 73-80 (1964)]
- Figures 1 and 2 show the results of the analysis by Fig. 1 and Fig. 2.
- Fig. 1 shows the average mortality of four kinds of fine leaf plants (a, b, c, k), and Fig. 2 shows seven kinds of broadleaf plants (d, e, f, g, h, i, j) mean mortality.
- d e, f, g, h, i, j
- Figure 1 shows the iso-effect line with a growth inhibition rate of 95% for fine leaf plants.
- Figure 2 shows an iso-effect line with a 95% growth suppression rate for broadleaf plants ⁇ .
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Application Number | Priority Date | Filing Date | Title |
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KR1019920703207A KR930701392A (ko) | 1990-06-11 | 1992-12-11 | 디페닐 에테르 유도체의 r - 광학 이성체 및 이것을 유효 성분으로 하는 제초제 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14986590 | 1990-06-11 | ||
JP2/149865 | 1990-06-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1991019694A1 true WO1991019694A1 (fr) | 1991-12-26 |
Family
ID=15484346
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1991/000714 WO1991019694A1 (fr) | 1990-06-11 | 1991-05-28 | Isomere optique de la forme r d'un derive d'ether de diphenyle, et herbicide le contenant a titre d'ingredient actif |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0533925A1 (ja) |
KR (1) | KR930701392A (ja) |
AU (1) | AU7892091A (ja) |
CA (1) | CA2084874A1 (ja) |
WO (1) | WO1991019694A1 (ja) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52111528A (en) * | 1976-03-17 | 1977-09-19 | Ishihara Sangyo Kaisha Ltd | Phenoxyphenoxyalkane carboxylic acid derivatives and herbicidal compos ition containing the same |
JPS60181048A (ja) * | 1984-02-04 | 1985-09-14 | バイエル・アクチエンゲゼルシヤフト | 光学活性のフエノキシプロピオン酸誘導体 |
JPH01163152A (ja) * | 1987-03-05 | 1989-06-27 | Teijin Ltd | フェノキシカルボン酸類およびそれを有効成分とする除草剤 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH626318A5 (ja) * | 1977-03-08 | 1981-11-13 | Ciba Geigy Ag | |
DE2961372D1 (en) * | 1978-01-20 | 1982-01-28 | Ciba Geigy Ag | Phenoxy-phenoxy-alkylcarboxylic acid derivatives with herbicidal activity, their preparation, compositions containing them and their use |
-
1991
- 1991-05-28 CA CA002084874A patent/CA2084874A1/en not_active Abandoned
- 1991-05-28 AU AU78920/91A patent/AU7892091A/en not_active Abandoned
- 1991-05-28 WO PCT/JP1991/000714 patent/WO1991019694A1/ja not_active Application Discontinuation
- 1991-05-28 EP EP91909702A patent/EP0533925A1/en not_active Withdrawn
-
1992
- 1992-12-11 KR KR1019920703207A patent/KR930701392A/ko not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52111528A (en) * | 1976-03-17 | 1977-09-19 | Ishihara Sangyo Kaisha Ltd | Phenoxyphenoxyalkane carboxylic acid derivatives and herbicidal compos ition containing the same |
JPS60181048A (ja) * | 1984-02-04 | 1985-09-14 | バイエル・アクチエンゲゼルシヤフト | 光学活性のフエノキシプロピオン酸誘導体 |
JPH01163152A (ja) * | 1987-03-05 | 1989-06-27 | Teijin Ltd | フェノキシカルボン酸類およびそれを有効成分とする除草剤 |
Non-Patent Citations (1)
Title |
---|
See also references of EP0533925A4 * |
Also Published As
Publication number | Publication date |
---|---|
EP0533925A1 (en) | 1993-03-31 |
EP0533925A4 (ja) | 1994-03-30 |
CA2084874A1 (en) | 1991-12-12 |
KR930701392A (ko) | 1993-06-11 |
AU7892091A (en) | 1992-01-07 |
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