WO1990002113A1 - Derives d'oxime et herbicides les contenant en tant qu'ingredients actifs - Google Patents

Derives d'oxime et herbicides les contenant en tant qu'ingredients actifs Download PDF

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Publication number
WO1990002113A1
WO1990002113A1 PCT/JP1988/000837 JP8800837W WO9002113A1 WO 1990002113 A1 WO1990002113 A1 WO 1990002113A1 JP 8800837 W JP8800837 W JP 8800837W WO 9002113 A1 WO9002113 A1 WO 9002113A1
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Prior art keywords
group
carbon atoms
benzaldehyde
compound
chloro
Prior art date
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PCT/JP1988/000837
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English (en)
Japanese (ja)
Inventor
Shizuo Azuma
Toshiyuki Hiramatsu
Koji Nakagawa
Yataro Ichikawa
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Teijin Limited
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Publication date
Application filed by Teijin Limited filed Critical Teijin Limited
Priority to PCT/JP1988/000837 priority Critical patent/WO1990002113A1/fr
Priority to PCT/JP1989/000864 priority patent/WO1990001874A1/fr
Priority to EP89909629A priority patent/EP0433451A1/fr
Priority to AU40752/89A priority patent/AU619038B2/en
Priority to EP90301439A priority patent/EP0442172A1/fr
Publication of WO1990002113A1 publication Critical patent/WO1990002113A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals

Definitions

  • the present invention relates to a novel oxime derivative and a herbicide containing the same as an active ingredient. More specifically, the present invention exhibits excellent herbicidal activity against broadleaf weeds and fineleaf weeds, and, depending on the method of use, the method of treatment, and the amount of treatment, does not substantially impair the growth of the crop. It relates to a herbicide having a property. Description of the prior art
  • herbicides that selectively kill broadleaf weeds such as 2,4-dichlorophenoxyacetic acid
  • selective herbicidally active compounds are known as selective herbicidally active compounds.
  • the selective herbicidal activity of 2,4 diclomouth phenoxyacetic acid is a selective herbicidal activity between fine plants including crop plants and weeds and broadleaf plants also including crop plants and weeds .
  • 2,4-Dichlorophenoxyacetic acid is known to have extremely low or no activity on narrow-leaved plants (see, for example, Mature, 155, 498 (1945)).
  • aromatic groups are Introduced compounds such as chloro- or trifluryl-substituted methyloxy groups or chlor- or trifluryl-methyl-substituted pyridyl oxy groups, etc., have the activity of selectively killing fine plants. It is also known
  • N-phosphonomethylglycine derivatives Herbicides containing certain N-phosphonomethylglycine derivatives as main active ingredients are known and commercially available.
  • This N-phosphonomethylglycine derivative is basically a non-selective herbicide, but at a low dose, it can be used for herbicides against perennial weeds, such as lycopodium, and broadleaf weeds, such as akaza and asaibu. Activity is reduced. Especially on convolvulaceous weeds such as Malva morning glory, they show almost no herbicidal effect even after 2 weeks of treatment.
  • N-phosphonomethylglycine derivatives are slow-acting and are not suitable for quickly removing weeds on agricultural or non-agricultural lands and performing the following operations.
  • An object of the present invention is to provide a novel oxime derivative.
  • Another object of the present invention is to provide a herbicide having excellent herbicidal activity against broadleaf weeds and fineleaf weeds.
  • Yet another object of the present invention is to provide substantially no harm to useful crops, especially soybeans and corn, depending on the method of use, the method of treatment and the amount of treatment, and thus to substantially inhibit their growth. It is an object of the present invention to provide a selective compound for destroying broadleaf weeds and fineleaf weeds and a herbicide containing the same.
  • Still another object of the present invention is to act on plants to kill or suppress the growth of many broad-leaf and fine-leaf grasses, and to reduce the growth of narrow-leaf crops such as sorghum and broad-leaf crops such as soybean.
  • Still another object of the present invention is to provide weeds for weeding purposes.
  • by spraying on the foliage not only killing or growth can be suppressed, but also by applying to soil before germination, the germination and growth of useful crops are not substantially inhibited by germination and growth of useful crops.
  • An object of the present invention is to provide a selective herbicide that can control growth and kill a growing body, that is, a herbicide that can be applied to both foliage application and soil treatment.
  • Still another object of the present invention is to provide a herbicide having low animal and fish toxicity and low soil persistence.
  • Still another object of the present invention is to use the above novel oxime derivative of the present invention together with an N-phosphonomethylglycine derivative known per se to take advantage of these herbicidal properties to make comparisons.
  • An object of the present invention is to provide a herbicidal composition and a method capable of killing both narrow-leaf and broad-leaf weeds at an extremely low application rate.
  • X and Y are the same or different and are each a hydrogen atom, a halogen atom, one CF3 or an alkyl group having 1 to 5 carbon atoms.
  • R 1 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R 2 is a hydrogen atom; a halogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or 1 COR 4 (where R 4 is a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or
  • alkyl groups ⁇ . ⁇ Saturated or unsaturated aliphatic carbon hydrocarbon group having to carbon atoms, which may have I ⁇ 10 substituted; halogen atom, a hydroxyl group, one C F3 - N0 2, - C ⁇ , alkyl ⁇ 5 carbons Group, carbon number ⁇ ! 5 to 5 alkoxy, 1 GOR 4 , a phenyl group optionally substituted with a halogen atom or 110 F 3, or a phenoxy group optionally substituted with a halogen atom or 1 CF 3.
  • An aromatic hydrocarbon group having 6 to 20 carbon atoms; or a halogen atom,
  • R 3 is a hydrogen atom or a halogen atom, a hydroxyl group, an aliphatic hydrocarbon group having an alkoxy group or ten OR 4 carbon atoms but it may also be substituted with I ⁇ 10.
  • R 2 is a hydrogen atom and R 3 is a hydrogen atom, an alkyl group, a cycloalkyl group or an aralkyl group, both X and Y are not hydrogen atoms.
  • the inventive oxime derivative of the present invention has a wide range of herbicidal spectrum showing excellent herbicidal activity against broadleaf weeds and fine-leafed weeds. Furthermore, depending on the method of use, treatment method, amount of treatment, etc., useful crops, especially soybeans and sorghum, do not substantially damage the phytotoxicity, and thus do not substantially inhibit the growth of these crops, and can be used for broadleaf weeds and narrowleaf weeds. It is a herbicide that can be destroyed. In addition, the oxime derivative of the present invention has a herbicidal effect even in a small amount, and has a fast-acting herbicidal activity. DESCRIPTION OF THE PREFERRED EMBODIMENTS OF THE INVENTION
  • X and Y are the same or different and are each a hydrogen atom, a halogen atom, a 10 F 3 or an alkyl group having 1 to 5 carbon atoms.
  • a halogen atom is, for example, fluorine, chlorine, bromine, etc. is there.
  • the alkyl group having from 5 to 5 carbon atoms may be linear or branched, such as methyl, ethyl, n-propyl, iso-propyl, ⁇ -butyl, sec-butyl, iso.
  • at least one halogen atom of X and Y is preferably a ten F3 or alkyl Le group with carbon number I ⁇ 5, an X gar CF 3, Y is a halogen atom Is particularly preferred.
  • R 1 is a hydrogen atom or an alkyl group having ⁇ to 5 carbon atoms, wherein the alkyl group having ⁇ to 5 carbon atoms is the same as the specific examples described above for X and ⁇ . Examples of the alkyl group include 5. R 1 is preferably a hydrogen atom.
  • R 2 is a hydrogen atom; a halogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or —COR 4 (here, a hydroxyl group, an alkyl group having 1 to 5 carbon atoms).
  • ⁇ A saturated or unsaturated aliphatic hydrocarbon group having from ⁇ to 10 carbon atoms which may be replaced by; a halogen atom, a hydroxyl group, -C Fa, -NOz, -CN, an alkyl group having ⁇ 5 carbon atoms, an alkoxy group having ⁇ 5 carbon atoms, — ⁇ OR 4 , a halogen atom or a phenyl group optionally substituted by 1 C F3, or A halogen atom or a phenoxy group which may be substituted with CF 3 , an aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted with cfc, or a halogen atom,
  • the aliphatic hydrocarbon group includes a linear or branched hydrocarbon group and an alicyclic hydrocarbon group.
  • the aromatic hydrocarbon group may be a single benzene nucleus or a naphthalene nucleus, or a combination thereof.
  • the aromatic heterocyclic group has a structure in which, for example, ⁇ or more carbon atoms in a benzene nucleus or a naphthalene nucleus are substituted with an oxygen atom, a nitrogen atom, a nitrogen atom, or the like.
  • the alkoxy group having 1 to 5 carbon atoms may be linear or branched, for example, methoxy, ethoxy, ⁇ -propoxy, iso-propoxy, n-butoxy. sec—butoxy, 1: butoxy, ⁇ -pentyl.
  • Examples of the halogen atom and the alkyl group having 1 to 5 carbon atoms include the same halogen atom and the same alkyl group having 1 to 5 carbon atoms as those described above for X and Y.
  • the main skeleton of R 2 includes vinyl, probenyl, butenyl, pentenyl, ethynyl, propenyl and the like.
  • 2-7 unsaturated aliphatic hydrocarbon groups, aromatic hydrocarbon groups having 6-15 carbon atoms such as phenyl and naphthyl, pyridyl, piperazine, quinolyl, quinoxalyl, quinazolyl, pyridazinyl, pyrimidyl, triliazinyl, etc. Is preferably an aromatic heterocyclic group having 3 to 1 carbon atoms containing a nitrogen atom.
  • an unsaturated aliphatic hydrocarbon group has no substituent
  • an aromatic hydrocarbon group and an aromatic heterocyclic group have no substituent or a halogen atom, — ⁇ F3, -NOz, -CN, methyl group, or It is preferably substituted with a methoxy group.
  • R 2 is a propenyl group as an unsaturated aliphatic hydrocarbon group, is unsubstituted as an aromatic hydrocarbon group, or is substituted with a halogen atom CF3, -NOz, -CN, methyl or methoxy.
  • the phenyl group and the aromatic heterocyclic group include a pyridyl group which may be unsubstituted or substituted with a hydrogen atom, a halogen atom, 1 N ⁇ , — ⁇ N, methyl or methoxy. Particularly preferred is a piperazyl group, a quinolyl group or a pyridazinyl group.
  • the aliphatic hydrocarbon for R 3 in the above formula (I) is a linear or branched chain hydrocarbon group, an alicyclic group, or a chain hydrocarbon group substituted with an aromatic hydrocarbon group.
  • Ha port Gen atom, an alkoxy group, - COR 4 is the same halogen atom as specific examples given above for R 2, an alkoxy group, - COR 4 Can be mentioned.
  • R 3 is a linear aliphatic hydrocarbon having 5 to 5 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, etc.
  • R 2 is a hydrogen atom and R 3 is a hydrogen atom, an alkyl group, a cycloalkyl group, or an aralkyl group
  • both X and Y are not hydrogen atoms.
  • ⁇ is a hydroxyl group, salts thereof may be used.
  • compounds exhibiting particularly excellent herbicidal activity are each particularly preferably selected from the following.
  • R 2 :-CH 2 -CH CH 2 , ⁇ i— N:
  • R 7 is hydrogen atom, halogen, one CN
  • R 4 ' is a hydroxyl group, a methoxy group, an ethoxy group, a propoxy group or a butoxy group.
  • Examples of the oxime derivative of the above formula (I) include the following compounds.
  • the compound of the above formula (e) can be produced, for example, by the following reaction method. ⁇ Hz N-0-R 2
  • the above-mentioned oxime derivatives of the formula (I) of the present invention affect the metabolism of plants, for example, suppress the growth of certain plants, regulate the growth of certain plants, and dwarf certain plants. Or has the property of killing 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.
  • the plant that is trying to inhibit growth is a plant that seeks to regulate metabolism, the seeds of such a plant, the place where such a plant is growing, or such a plant. Applied in places where growth is expected, with sufficient cloudiness to regulate plant metabolism.
  • the compounds according to the invention can regulate the metabolism of plants, for example in an amount of 0.001 to 20 kg / ha, more preferably in an amount of 0.005 to 10 kg / ha, particularly preferably in an amount of 0.01 to 5 kg / ha. it can.
  • the compound of the present invention can be used as a preparation in a usual form such as a solution, an emulsion, a suspension, a powder, a paste or a granule.
  • Such preparations include, for example, talc, bentonite, flaky kaolin, diatomaceous earth, white carbon, vermikinifi Solid carriers such as ethanol, slaked lime, ammonium sulfate, and urea; water, alcohol, dioxane, acetate, xylene, cyclohexane, methyl naphthalene, dimethylformamide, N-methylvinylidone, dimethylsulfoxide, Liquid carriers such as cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone; alkyl sulfates, alkyl sulfonates, lignin sulfonates, polyxylene ethylene glycol alcohol, polyxylene ethylene glycol Use one or more of surfactants, emulsifiers or dispersants, such as mono-ter, poly-xylethylene sorbitan monoalkylate, and dinaphthylme
  • Such a preparation can be prepared, for example, by mixing the compound with the above-mentioned carrier and a carrier or emulsifier.
  • the compounds of the invention can be present in the formulations usually in a proportion of from 0.01 to 99% by weight, preferably from 0.1 to% by weight.
  • the compounds of the invention may be applied to the plants as such, or in a mixture with other active compounds, or in the form of a formulation as described above, for example by conventional means such as spraying, spraying, dusting or dusting. Can be.
  • the compound of the present invention When the compound of the present invention is used for the purpose of inhibiting the growth or extermination of harmful plants, the compound of the present invention may be used as it is. Or in the form of a composition, where the beneficial plants or their seeds and the harmful plants or their seeds coexist or are likely to coexist, in order to suppress the growth of plants that are harmful to these plants or seeds directly or to the upper lands. It can be applied in an amount sufficient to destroy it.
  • Harmful plants are generally human-created environments, for example, plants that enter and propagate from the surrounding natural world in fields, or that are perceived by humans to be useless or harmful in that environment. Such harmful plants are generally referred to as weeds. As weeds, for example, the following various species are targeted.
  • Ainubu (Amaranthus 1 i idus),
  • Akaza (Chenopod ium album var. Centrorubrum), Core kaza (Chenopod i urn f icifol ium),
  • Solanaceae Solanaceae
  • Tequili spanicam pan i cum texanum
  • a family (Pontederiaceae);
  • the compound of the above formula (I) substantially does not cause harm to useful crops, especially soybeans and maize sorghum, depending on the method of use, treatment method and treatment, and therefore substantially inhibits their growth. It can also be used as a selective herbicide to destroy broadleaf weeds and narrowleaf weeds.
  • the compound of the present invention can not only suppress the death or growth by spraying on the foliage of a weed to be removed, but also germinate it. By applying it to soil beforehand, it can be used as a selective herbicide that does not substantially inhibit the germination and growth of useful crops and can suppress the 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.
  • the compound of the formula (I) of the present invention is used together with another compound having an excellent herbicidal activity against, for example, narrow leaf weeds so as to sufficiently exert herbicidal activity against broad-leaved weeds and narrow leaf weeds. It can be used to provide an effective herbicide composition for both broadleaf weeds and fineleaf weeds.
  • R21 and R22 are the same or different and is an 0H or a OR 24 respectively, R £ ⁇ - 0H, there Hide -OR 2 4 or a NR 25 R 2.
  • R 24 is an alkyl group having 5 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 phenoxy groups.
  • R 25 and R 26 are the same or different each represents a hydrogen atom, an alkyl group of ⁇ 5 carbon atoms, a hydroxyalkyl group ⁇ 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, also, R 25 and R 26 Can form morpholino, piperidino or pyrrolidino groups together with the nitrogen atom to which they are attached.
  • R 21 and R 22 are the same or different, each being 10 ° or 100 R 24
  • R 20 is — 0 ⁇ , 10 R 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, and a C 2 to 5 carbon atom.
  • R 25 and R 26 are the same or different and are respectively a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group having 1 to 5 carbon atoms, and an alkynyl group having 2 to 5 carbon atoms.
  • 5 and R 6 can form a morpholino, piperidino or pyrrolidino group together with the nitrogen atom to which they are attached.
  • Examples of the alkyl group for R 24 , R 5 and are the same as those described above for X and Y in the formula (I).
  • examples of the haloalkyl group having 1 to 5 carbon atoms include halomethyl, haloethyl, dihaloethyl, and! ⁇ Mouth propyl, halobutyl and halopentyl can be mentioned.
  • examples of the halogen atom include fluorine, chlorine, and bromine.
  • Examples of the alkenyl group having 2 to 5 carbon atoms for R 24 , R 25 and R 26 include vinyl, propenyl, butenyl and pentenyl.
  • alkoxyalkyl group for R 24 for example, methoxethyl, ethoxyxyl and the like can be mentioned as preferred.
  • Preferred haloalkoxyalkyl groups for R 24 include, for example, chloroethoxyl and chloromethoxyl.
  • alkoxyalkoxyalkyl group for R 24 include methoxyxethyl and ethoxyxethyl.
  • hydroxy ⁇ alkyl group having 1 to 5 carbon atoms for R 26, such as hydroxymethyl, hydroxy Shechiru can ani gel as preferred hydroxy pentyl.
  • the compound of the above formula (H) can also be used in the composition of the present invention 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 2.5 or less is preferable.
  • a strong acid having a pKa of 2.5 or less is preferable.
  • examples of such an acid include hydrochloric acid, sulfuric acid, phosphoric acid, trifluroacetic acid, and trichloroacetic acid.
  • R 21 , R 22 and R 23 in the above formula ( ⁇ ) represents 100, for example, a salt thereof with an alkali metal, alkaline earth metal, copper , Zinc, ammonium or organic ammonium Formed as a salt with the cation.
  • 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, for example, those having a molecular weight of about 300 or less.
  • organic amines are, for example, alkylamines, alkylenepolyamines and alkanolamines, such as methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isoptyramine, secondary-butylamine, n-amylamine.
  • R 21 , R 22 and R 23 are salts of 10H, and R 21 , Compounds in which the remaining one of R22 and R23 is 100H can be mentioned.
  • the salt of 1 OH include ammonium or organic ammonium (where the organic ammonium group is a monoalkyl ammonium, a dialkyl ammonium, a trialkyl ammonium, a monoalkenyl ammonium, a dialmium).
  • the salt of the compound of the above formula ( ⁇ ) with the acid or base as described above is produced from the compound of the above formula ( ⁇ ) and the acid or base according to a method known per se.
  • Examples of the compound of the above formula (II), the acid addition salt or the salt thereof with a base which are preferably used in the present invention are as follows.
  • composition of the present invention comprising the compound of the above formula (e) and the compound of the formula (E) comprises a compound of the above formula (I) and a compound of the formula (I) It is preferable that the compound is contained in a ratio by weight of the former (e) to the latter ( ⁇ ) of ⁇ : 5 to 50: ⁇ , and the ratio is more preferably 1: 20 to 20: 1, particularly preferably 1:10 to 10: ⁇ .
  • 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 from 0.1 to 10 kg / ha, preferably from 0 to 10 kg / ha. An amount of 5 to 5 KgZ ha is appropriate. Particularly suitable proportions also without a large number of experiments by conventional tests Bok which is standardized by those skilled in the art, u amount used can be readily determined by
  • 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 normal form preparation such as a solution, emulsion, suspension, powder or paste.
  • composition of the present invention can be prepared by combining the compound (I) and the compound (H) and then mixing the compound (I) with a carrier or the like to prepare a preparation.
  • a carrier or the like to prepare a preparation.
  • composition of the compound (I) and the compound (E) are separately prepared, and if necessary, carriers and the like are added. It can be prepared by, for example, a method of mixing the products together to form a preparation.
  • a weed comprising applying the compound (I) and the compound () simultaneously or in an arbitrary order to a place where the weed is growing in an amount effective for killing the weed. It is a method of killing.
  • the compound (I> and the compound (n) may be referred to as the above composition containing these compounds (I> and (E)) or separately prepared as a composition of the compound (I) and the compound (I).
  • the composition of I By applying together the composition of I), it can be applied simultaneously to the place where weeds are growing.
  • composition of compound (I) and the composition of compound (I) separately prepared can be applied to a place where weeds grow over time.
  • the application order of the composition of the compound (I) and the composition of the compound (I>) 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.
  • the compound (e) By applying the compound (E>) before the crop emerges, the crops that grow there will die before the crop emerges, and the crop will grow smoothly.
  • the application rates of the compounds (I). And (E) are appropriately determined based on the application rates described for the composition.
  • parts means parts by weight.
  • the herbicidal activity was evaluated on a six-point scale unless otherwise specified. That is, after the active compound is applied, the healthy state, which is almost the same as before the application, is set to 0, and the whole plant is wilted and withered by the application of the active compound is set to 5, during which 4 steps according to the strength of the plant ( ⁇ , 2, 3, and 4> were provided for evaluation.
  • Example II 2-ethoxy-14-1 (2-chlor-4-methylphosphonyl) benzaldehyde 3. 2-45 instead of 45 parts 2- (methoxycarbonylcarbonyl) 1-4 — (2-Chloro-41-trimethyl romethylf: L-noxy) Using benzaldehyde (4.03 parts), the reaction was followed in exactly the same manner to obtain 3.85 parts of the desired product. Table 8 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of the compound.
  • Example 1 ( Four ) In Example I, instead of 0.7 parts of hydroxylamine hydrochloride, 0.84 parts of 0-methylhydroxylamine hydrochloride was used, and the reaction and post-treatment were carried out in exactly the same manner to obtain 3.80 parts of the target compound.
  • Table 18 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of the compound.
  • Example 2 instead of 0.7 parts of hydroxylamine hydrochloride, 0.84 parts of 0-methylhydroxylamine hydrochloride was used, and the reaction and post-treatment were carried out in exactly the same manner to obtain 3.85 parts of the desired product.
  • Table 8 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of the compound.
  • Example ⁇ 2 (2- ( ⁇ -methoxycarbonyloxy) 1-41 (2-chloro-4-trimethylfuromethylphenoxy) Benzaldehyde Instead of 4.03 parts, 2— (1-ethoxycarbonyl) Toxy> 1.41 (2-chloro 4-trifluoromethylphenoxy) 4.16 parts of benzaldehyde was used, and the reaction and post-treatment were carried out in exactly the same manner to obtain 3.90 parts of the desired product.
  • the infrared absorption spectrum and the nuclear magnetic resonance spectrum of the compound are shown in Table 18.
  • Example 16 Synthesis of 0 CHC 00 C Ha (15) CH 3 In Example 6 as 0-substituted hydroxylamine Using 0-2-propylhydroxylamine, the reaction and post-treatment were carried out in the same manner as described above to obtain 3.0 parts of the desired product. Table 18 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of the compound.
  • Example 16 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of the compound.
  • Example 1 2-ethoxy-4- (2-chloro-4-trimethylphenoxy) benzaldehyde 3.45 parts instead of 2.45 parts 2- ( ⁇ -methoxycarbonyl) Xish> 14- (2-chloro-1-4-trimethylfuromethylphenoxy) 4.17 parts of acetophenone were used, and the reaction and after-treatment were carried out in the same manner to obtain 3.0 parts of the target compound.
  • Table 18 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of the compound.
  • Example 6 Synthesis of In Example 6, 0.8 part of 0-methylhydroxylamine hydrochloride was used in place of 0.7 part of hydroxylamine hydrochloride, and the reaction and post-treatment were carried out in the same manner to obtain 3.1 parts of the desired product.
  • Table 18 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of the compound.
  • Example No. 8 In Example No. 8, 2— ( ⁇ —Methoxycarbonylethoxy) 1-4— (2—Chloro-4-l / fluoromethylphenoxy) benzaldehyde 4.0 2- (ethoxy) instead of 03 parts 1. 4- (2-chloro-4-trimethyl rophenoxy) 3.45 parts of benzaldehyde, and 1.1 parts of 0-phenylhydroxylamine instead of 1.23 parts of 0-benzylhydroxylamine, Thereafter, the reaction and post-treatment were carried out in exactly the same manner to obtain 3.70 parts of the desired product.Table 18 shows the infrared absorption spectrum and nuclear magnetic mirror spectrum of the compound. Show.
  • Example 20 2- ( ⁇ -methoxycarbonylethoxy) 1-41 (2-chloro-4-trifluryl-methylphenoxy) Instead of 4.03 parts of benzaldehyde, 2- ( ⁇ methoxyethoxycarbonyl) Xi> 1-41 (2, Fluorofoxy) Use benzaldehyde (3.70 parts) and 0-substituted hydroxylamine as shown in Table 13 below. As a result, each product was obtained in the weight shown in Table 13. The infrared absorption spectrum and nuclear magnetic resonance spectrum of each product are shown in Table 18. Table 1 3
  • Example 20 In Example 20, 2— ( ⁇ —Methoxycarbonyl 1-4-1 (2-Chloro-4-trimethyl ro-methylphenoxy) Benzaldehyde Instead of 4.03 parts 2- (1-methoxycarbonyldimethoxy) 1-4-1 (4-Trifluoromethyl roxinoxy) ) Using 3.68 parts of benzaldehyde and 0-substituted hydroxylamine as shown in Table 14 below, the reaction and post-treatment were carried out in exactly the same manner to obtain the respective weights shown in Table 14 below. Table 18 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of each product.
  • Example 20 Synthesis of Compounds (59) to (5 ⁇ ) In Example 20, the same reaction and post-treatment were carried out in exactly the same manner as in Example 20 except that the 0-substituted hydroxyylamine shown in Table 15 below was used.
  • the target product was obtained with the weight shown in Table 1-5.
  • Table 18 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of each product.
  • Example 38 the 0-substituted hydroxylamine shown in Table 16 below was used, and the reaction and post-treatment were carried out in exactly the same manner to obtain the desired product in the weight shown in Table 16 below. I got Table 18 shows the infrared absorption spectrum and nuclear magnetic resonance spectrum of each product. 6
  • Example 2 In Example 2 2-( ⁇ -methoxycarbonyloxy) 14-(2-chloro-1-4-trifluoromethylphenoxy) Benzaldehyde Instead of 4.03 parts of 2-(4.0-methoxycarbonyl) Ethoxy> 4- (4-trimethylaminophenoxy) Using 3.68 parts of benzaldehyde, the 0-substituted hydroxyylamine shown in Table 17 below was used, and the rest was exactly the same. The desired product was obtained by the reaction and post-treatment, each having the weight shown in Table 17. The infrared absorption spectrum and nuclear magnetic resonance spectrum of each product were obtained. The vectors are shown in Table 8 Table 1 7
  • Example 20 2- ( ⁇ -methoxycarbonylethoxy) 1-41 (2-chloro-1-4-trimethylfuromethylphenoxy) benzaldehyde 2-hydroxy-1-41 instead of 4.03 parts of benzaldehyde 2-Chloro-1-tetrafluoromethylphenoxy) Using 3.17 parts of benzaldehyde, the reaction and post-treatment were carried out in the same manner as described above to obtain 2.90 parts of the desired product. The nuclear magnetic resonance spectrum is shown in Table 18.
  • Example 65 2- ( ⁇ -methoxycarbonylethoxy) 1-41 (2-chloro-1-4-trimethylfuromethylphenoxy) benzaldehyde 2-hydroxy-1-41 instead of 4.03 parts of benzaldehyde 2-Chloro-1-tetrafluoromethylphenoxy
  • the active compounds according to the invention were prepared according to Preparation Example 1 above. Plants were sown on soil and cultivated for 2-3 weeks after germination.
  • Seeds of the plants to be evaluated are sown on the soil, treated on the second day after sowing as follows, and observed for 3 weeks for plant growth.
  • a mixed solvent of water and acetone (volume ratio 1: 1, non-ionized) was prepared so that each of the oxime derivative and the ⁇ -phosphonomethylglycine derivative shown in Table 1 ⁇ at a predetermined mixing ratio and in a predetermined treatment amount.
  • Plants were cultivated in a Darin house for 2-3 weeks after germination by sowing or rhizome transplantation in a plastic pot (diameter 10 cm) containing soil.
  • the herbicidal activity was examined by applying the above-mentioned preparation solution to this plant so that the total applied volume was 4 (00 cm 2 ).
  • the herbicidal composition of the present invention has a faster and faster onset of herbicidal activity as compared to the case where the N-phosphonomethyldaricin derivative is used alone. Excellent in nature.
  • the N-phosphonomethyldaricin derivative When used alone, the herbicidal activity of broadleaf grasses such as morning glory and American stag is reduced, especially at low doses, and the activity is reduced even U days after the treatment. Either rarely indicated or insufficient.
  • the composition of the present invention for example, the composition of Test Example 5 can kill all the weeds described in Table II in about one week.
  • the composition of the present invention is surprisingly improved in synergistic effects by applying a combination of the oxime derivative and the N-phosphonomethyldaricin derivative as a synergistic effect. We found that the expansion of the herbicidal skull became remarkable.

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  • Organic Chemistry (AREA)
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Abstract

Composés de dérivés d'oxime spécifiques ou leurs sels et composés herbicides contenant lesdits composés en tant qu'ingrédients herbicides. Les dérivés d'oxime sont très efficaces contre les mauvaises herbes, aussi bien à feuilles larges qu'à feuilles étroites, et leur action est rapide même si on ne les utilise qu'en faibles quantités.
PCT/JP1988/000837 1988-08-24 1988-08-24 Derives d'oxime et herbicides les contenant en tant qu'ingredients actifs WO1990002113A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
PCT/JP1988/000837 WO1990002113A1 (fr) 1988-08-24 1988-08-24 Derives d'oxime et herbicides les contenant en tant qu'ingredients actifs
PCT/JP1989/000864 WO1990001874A1 (fr) 1988-08-24 1989-08-23 Derives d'oximes et herbicides les contenant en tant qu'ingredient actif
EP89909629A EP0433451A1 (fr) 1988-08-24 1989-08-23 Derives d'oximes et herbicides les contenant en tant qu'ingredient actif
AU40752/89A AU619038B2 (en) 1988-08-24 1989-08-23 Oxime derivatives and herbicides containing the same as an active ingredient
EP90301439A EP0442172A1 (fr) 1988-08-24 1990-02-12 Dérivés d'oximes et herbicides les contenant comme ingrédient actif

Applications Claiming Priority (1)

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PCT/JP1988/000837 WO1990002113A1 (fr) 1988-08-24 1988-08-24 Derives d'oxime et herbicides les contenant en tant qu'ingredients actifs

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WO1990002113A1 true WO1990002113A1 (fr) 1990-03-08

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6924313B1 (en) 1999-09-23 2005-08-02 Pfizer Inc. Substituted tertiary-heteroalkylamines useful for inhibiting cholesteryl ester transfer protein activity
US7122536B2 (en) 1999-09-23 2006-10-17 Pfizer Inc. (R)-chiral halogenated substituted fused heterocyclic amino compounds useful for inhibiting cholesterol ester transfer protein activity

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53108937A (en) * 1977-03-02 1978-09-22 Ciba Geigy Ag Oximether and oximester process for preparing same plant growth stimulating and protecting agent and method therefor
JPS5535006A (en) * 1978-09-01 1980-03-11 Ciba Geigy Ag Diphenyletherroxime derivative*herbicidal agent and method containing it
JPS61140546A (ja) * 1984-12-12 1986-06-27 Asahi Chem Ind Co Ltd 新規なα−メトキシアセトフエノン誘導体及びそれを有効成分とする除草剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53108937A (en) * 1977-03-02 1978-09-22 Ciba Geigy Ag Oximether and oximester process for preparing same plant growth stimulating and protecting agent and method therefor
JPS5535006A (en) * 1978-09-01 1980-03-11 Ciba Geigy Ag Diphenyletherroxime derivative*herbicidal agent and method containing it
JPS61140546A (ja) * 1984-12-12 1986-06-27 Asahi Chem Ind Co Ltd 新規なα−メトキシアセトフエノン誘導体及びそれを有効成分とする除草剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6924313B1 (en) 1999-09-23 2005-08-02 Pfizer Inc. Substituted tertiary-heteroalkylamines useful for inhibiting cholesteryl ester transfer protein activity
US7122536B2 (en) 1999-09-23 2006-10-17 Pfizer Inc. (R)-chiral halogenated substituted fused heterocyclic amino compounds useful for inhibiting cholesterol ester transfer protein activity
US7253211B2 (en) 1999-09-23 2007-08-07 Pfizer Inc. (R)-chiral halogenated substituted fused heterocyclic amino compounds useful for inhibiting cholesterol ester transfer protein activity

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