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WO1987001699A1 - Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione - Google Patents

Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione Download PDF

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Publication number
WO1987001699A1
WO1987001699A1 PCT/US1985/001786 US8501786W WO8701699A1 WO 1987001699 A1 WO1987001699 A1 WO 1987001699A1 US 8501786 W US8501786 W US 8501786W WO 8701699 A1 WO8701699 A1 WO 8701699A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
effective amount
trans
cyclohexane
plants
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1985/001786
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English (en)
Inventor
Tatao Luo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron USA Inc
Original Assignee
Chevron Research and Technology Co
Chevron Research Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to RO142130A priority Critical patent/RO105610B1/ro
Priority to NL8520309A priority patent/NL193944C/nl
Priority to GB8708127A priority patent/GB2188321B/en
Priority to HU854220A priority patent/HU198605B/hu
Priority to BR8507282A priority patent/BR8507282A/pt
Priority to KR1019860700645A priority patent/KR920010518B1/ko
Priority to JP60504287A priority patent/JPS63500939A/ja
Application filed by Chevron Research and Technology Co, Chevron Research Co filed Critical Chevron Research and Technology Co
Priority to SE8603868A priority patent/SE458683B/sv
Priority to RO124783A priority patent/RO96716B1/ro
Priority to NO86863733A priority patent/NO162555C/no
Publication of WO1987001699A1 publication Critical patent/WO1987001699A1/fr
Priority to DK250087A priority patent/DK164856C/da
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C251/16—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings

Definitions

  • This invention relates to trans-2- .l-(3-chloro- allylamino) propylidene]-5-(2->-ethylthiopropyl)cyclohexane- 1,3-dione and salts thereof and to the use of such com- pounds as herbicides.
  • R is most preferably alkyl or 1 to 3 carbon atoms, most preferably ethyl or propyl;
  • R 1 is most preferably 3-trans-chloroallyl or 4-chlo- robenzyl
  • R 2 and R3 are preferably each alkyl or 1 to 3 carbon atoms or one of R or R- * is hydrogen and the other is alkylthioalkyl having 2 through 8 carbon atoms, most pre ⁇ ferably R 2 and R 3 are each methyl or one of R 2 or R 3 is hydrogen and the other is 2-ethylthiopropyl.
  • the compound of Formula I exhibits excellent phytotoxicity against grasses at even very low application rates and may be safely applied with respect to broad-leaf crops at such rates.
  • the present compound is espe- cially useful for controlling grassy weeds in broad-leaf crops and is ' especially useful to control grassy weeds in soybean crops.
  • the compound of the present invention can be represented by the following formula:
  • R x is 3-transchloroallyl
  • the invention also comprises compatible salts of the compound of Formula I.
  • the invention provides a herbicidal composition comprising a compatible carrier and a herbicidally effective amount of the compound(s) of the invention or mixtures thereof.
  • the present invention also provides a method for preventing or controlling the growth of unwanted grassy vegetation, which comprises treating the growth medium and/or the foliage of such vegetation with a herbicidally effective amount of the compound(s) of the invention or mixtures thereof.
  • the present invention also provides a method for regulating plant growth which comprises treating the growth medium and/or the foliage of such vegetation with a plant growth regulating effective amount of the co - pound(s) of the invention or mixtures thereof, effective to alter the normal growth pattern of said plants.
  • the present invention also provides chemical intermediates and processes for preparing the compounds of the invention.
  • the invention will be further described herein- below.
  • the compound of Formula (I) can be conveniently prepared by the following schematically represented pro ⁇ cess:
  • This process can be conveniently effected by contacting Compound (A) with 3-trans-chloroallyloxyamine (B), preferably in an inert organic solvent.
  • this process is conducted at tempera ⁇ tures in the range of about from 0 to 80°C, preferably about from 20 to 40°C, for about from 1 to 48 hours, pre- ferably about from 4 to 12 hours, using about from 1 to 2, preferably 1.05 to 1.2 moles of 3-trans-chloroallyloxy- amine (B) per mole of Compound (A) .
  • Suitable inert organic solvents which can be used include, for example, lower alkanols, e.g., ethanol, ethanol, ethers, e.g., ethyl ether; methylene chloride.
  • Two-phase water and immiscible organic solvent e.g.,- hexane
  • compatible mixtures thereof can also be used.
  • Trans-chloroallyloxyamine is a known compound and can be prepared via known procedures, such as, for example, described in my U.S. Patent No. 4,440,566.
  • a hydrochloride salt of- trans-chloroallyloxy ⁇ amine can be used by neutralizing the salt with an alkali metal alkoxide, in situ.
  • the starting materials of Formula (A) can be prepared via the general procedure described in my U.S. Patent No. 4,440 ,566.
  • the compatible salts of Formula (I) can be pre ⁇ pared by conventional procedures, for example, via the reaction of the compound of Formula I with a base, such as, for example, sodium hydroxide, potassium hydroxide and the like, having the desired cation. Additional varia ⁇ tions in the salt cation can also be effected via ion exchange with an ion exchange resin having the desired cation.
  • the reaction product can be recovered from its reaction product mixture by any suitable separation and purification procedure, such as, for example, chromato- graphy. Suitable separation and purification procedures "5- * - - - . .
  • reaction tempera- tures e.g., reaction tempera- tures, times, mole ratios of reactants, solvents, etc.
  • Optimum reaction conditions e.g., temperature, reaction time, mol ratios, solvents, etc.
  • optical isomer mixtures are obtained, the respective optical isomers can be obtained by conventional resolution procedures.
  • Geometric isomers can be separated by conventional separation procedures which depend upon differences. in physical properties between the geometric isomers. However, it is generally preferable to use the desired isomeric starting material in the reaction. Definitions
  • compatible salts refers to salts which do not significantly adversely alter the herbicidal properties of the parent compound.
  • Suitable salts include cation salts such as, for example, the cation salts of lithium, sodium, potassium, alkali earth metals, copper, zinc, ammonia, quaternary ammonium salts, and the like.
  • room temperature or “ambient tempera ⁇ ture” refers to about 20-25°C.
  • the compound of Formula (I) and its salts exhibit both pre- and post-emergent herbicidal activity and exhibit especially good herbicidal activity against grasses.
  • the compounds exhibit especially good phyto ⁇ toxicity against foxtail, Ber udagrass, crabgrass, rhizone Johnsongrass and volunteer corn which are weed species which are generally very difficult to control.
  • the herbicidal compounds are applied directly to the foliage or other plant parts.
  • the herbicidal compounds are applied to the growth medium, or prospective growth medium, for the plant.
  • the optimum amount of the herbicidal compound or composition will vary with the particular plant species, and the extent of plant growth, if any, and the particular part of the plant which is contacted and the extent of contact.
  • the optimum dosage can also vary with the general location, or environment (e.g., sheltered areas such as greenhouses compared to exposed areas such as fields) , and type and degree of control desired.
  • the present compounds are applied at rates ' of about from 0.02 to 60 kg/ha, preferably about from 0.02 to 10 kg/ha.
  • the compounds can be applied undiluted, in actual practice they are generally applied as a composition or formulation comprising an effective amount of the compound(s) and an acceptable car ⁇ rier.
  • An acceptable or compatible carrier is one which does not significantly adversely affect the desired biological effect achieved by the active compounds, save to dilute it.
  • the composition contains about from 0.05 to 95% by weight of the compound of Formula (I) or mixtures thereof.
  • Concen ⁇ trates can also be made having high concentrations designed for dilution prior to application.
  • the carrier can be a solid, liquid, or aerosol.
  • the actual compositions can take the form of granules, powders,
  • Suitable solid carriers which can be used include, for example, natural clays (such as kaolin, atta- pulgite, montmorillonite, etc.), talcs, pyrophyllite, diatomaceous silica, synthetic fine silica, calcium alumi- nosilicate, tricalciu phosphate, and the like.
  • organic materials such as, for example, walnut shell flour, cotton-seed hulls, wheat flour, wood flour, wood bark flour, and the like can also be used as carriers.
  • Suitable liquid diluents which can be used include, for example, water, organic solvents (e.g., hydrocarbons such as benzene, toluene, dimethylsulfoxide, kerosene, diesel fuel, fuel oil, petroleum naphtha, etc.), and the like.
  • Suitable aerosol carriers which can be used include con ⁇ ventional aerosol carriers such as halogenated alkanes, etc.
  • the composition can also contain various promo ⁇ ters and surface-active agents which enhance the rate of transport of the active compound into the plant tissue such as, for example, organic solvents, wetting agents and oils, and in the case of compositions designed for pre- emergence application agents which reduce the leachability of the compound or otherwise enhance soil stability.
  • Crop oils such as, for example, soybean oils, paraffin oils and olefinic oils, are especially advantageous as carriers or additives in that they enhance phytotoxicity.
  • the composition can also contain various com ⁇ patible adjuvants, stabilizers, conditioners, insecti ⁇ cides, fungicides, and if desired, other herbicidally active compounds.
  • One convenient concentrate formulation which can be used comprises 23-27% by weight of the active herbicide of the invention, 2 to 4% by weight of an emulsifier, for example, calcium alkylbenzene sulfonates, octylphenol- ethoxylate, etc., or mixtures thereof, and about 70-75% organic solvent, for example, xylene, etc.
  • an emulsifier for example, calcium alkylbenzene sulfonates, octylphenol- ethoxylate, etc., or mixtures thereof
  • organic solvent for example, xylene, etc.
  • the concen- trate is mixed with water and preferably a crop oil prior
  • the herbicide is applied as water emulsion containing about 0.02-0.6 wt. %, preferably 0.07-0.15 wt. % of the herbi ⁇ cide, of the invention; about ' 0.001-0.01 wt. % of an emul- sifier; about 0.08-2.5 wt. % of an organic solvent and about 95 to 99 wt. % water.
  • the composition also contains about 0.25 to 2 wt. % of a crop oil.
  • the application composition can be conveniently prepared by mixing the concentrate formulation with about 1/4 to 1/2 the desired amount of water. Then admixing the crop oil and then adding the remaining amount of water. If no crop oil is used, then the water and concentrate formulation are simply admixed together.
  • This example illustrates a procedure which can 35 be used to prepare the title compound.
  • a solution containing 0.01 mole of sodium hydroxide dissolved in 2 ml of wate is added to a solu ⁇ tion containing 0.01 mole of 2-[l-(3-trans-chloroallyl- oxyamino) propylidene-5-(2-ethylthiopropyl)-cyclohexane 40 1,3-dione at room temperature.
  • the solvents are evaporated off under vacuum affording the 1-hydroxy sodium salt of 2-[l-(3-trans-chlo- roallyloxyamino) propylidene-3-oxo-5-(2-ethylthiopropyl)- cyclohex-1-en-l-ol.
  • Example 3 the title compound of Example 1, i.e., 2-[l-(3-trans-chloroallyloxyamino) propylidene]- 5-(2-ethylthiopropyl)-cyclohexane-l ,3-dione was tested, using the procedures described hereinbelow, for pre-e er- gent and post-emergent phytotoxic activity against a variety of grasses and broad-leaf plants including one grain crop and one broad-leaf crop.
  • Pre-Emergent Herbicide Test i.e., 2-[l-(3-trans-chloroallyloxyamino) propylidene]- 5-(2-ethylthiopropyl)-cyclohexane-l ,3-dione was tested, using the procedures described hereinbelow, for pre-e er- gent and post-emergent phytotoxic activity against a variety of grasses and broad-leaf plants including one grain crop and one broad-lea
  • Pre-emergence herbicidal activity was determined in the following manner.
  • Test solutions of the respective compounds were prepared as follows: 355.5 mg of test compound was dissolved in 15 ml of acetone. 2 ml of acetone containing 110 mg of a non- ionic surfactant was added to the solution. 12 ml of this stock solution was then added to 47.7 ml of water which contained the same nonionic surfactant at a concentration of 625 mg/1.
  • Test compounds of the test vegetation were planted in a pot of soil and the test solution was sprayed uniformly onto the soil surface at a test compound dose of 27.5 micrograms/cm unless otherwise specified in the following Tables.
  • the pot was watered and placed in a greenhouse.
  • the pot was watered intermittently and observed for seedling emergence, health of emerging seed ⁇ lings, etc., for a 3-week period. At the end of this period, the herbicidal effectiveness of the compound was rated based on the physiological observations. A O-to-100 scale was used, 0 representing no phytotoxicity, 100 representing complete kill.
  • the results of these tests are summarized in Table 1.
  • Post-Emergent Herbicidal Test The test compound was formulated in the same manner as described above for the pre-emergent test.
  • This formulation was uniformly sprayed on 2 similar pots containing plants 2 to 3 inches tall (except wild oats, soybean and watergrass which were 3 to 4 inches tall) (approximately 15 to 25 plants per pot) at a test compound dose of 27.5 microgram/cm 2 unless otherwise specified in the following Tables. After the plants had dried, they were placed in a greenhouse and then watered intermit ⁇ tently at their bases as needed. The plants were observed periodically for phytotoxic effects and physiological and morphological responses to the treatment. After 3 weeks, the herbicidal effectiveness of the compound was rated based on these observations. A O-to-100 scale was used, 0 representing no phytotoxicity, 100 representing complete kill. The results of these tests are summarized in Table 2.
  • Example 3 the title compound of Example 1, of the present invention, (“1") was tested for post-emergence herbicidal activity at moderately low dosage rates side-by-side with its butylidene homolog, i.e. , trans-2-[l-(3-chloroal ' lyloxyamino)butylidene]-5-(2- ethylthiopropyl)-cyclohexane-1,3-dione.
  • the tests were conducted in the same manner as described in Example 2, hereinabove, with the exception that the application rates specified in Table 3 were used and 4 replicate pots were used per test instead of 2.
  • the average result of the four replicates are reported in Table 3 herein below, wherein 0 indicates no phytotoxicity and 100 indicates complete kill. Generally, phytotoxici- ties below about 20-30% are not considered significant because the plant can typically grow out of this amount of injury.
  • Example 4 the title compound (“1") was tested for post-emergence herbicidal activity at very low dosage rate side by side with trans-2-[l-(3-chloroallyl- oxyamino)butylidene]-5-(2-ethylthiopropyl)-cyclohexane- 1,3-dione ("C-l”) and the commercial herbicide Sethoxdm (“C-2") (i.e., 2-[l-(ethoxyamino)butylidene]-5-(2- ethylthiopropyl)-cyclohexane-l,3-dione against an expanded list of weed grasses.
  • C-l trans-2-[l-(3-chloroallyl- oxyamino)butylidene]-5-(2-ethylthiopropyl)-cyclohexane- 1,3-dione
  • C-2 commercial herbicide Sethoxdm
  • an application rate of Compound 1 of 0.11 q/cm 2 was about equivalent to an application rate of Compound C-l of 0.28 q/cm 2 to control crabgrass and barnyardgrass.
  • An application rate of Compound 1 of 0.05 q/c was about equivalent to an application rate of Compound C-l of 0.28 q/c to control yellow foxtail and an application rate of Compound 1 of 0.11 q/cm 2 was superior to an application rate of Compound C-l of 0.28 q/cm to control Johnsongrass

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Des composés de 2- AD1-(3-Chloroallyloxyamino)propylidène)-5-(2-éthylthiopropyle)-cyclohexane-1,3-dione et des sels obtenus à partir desdits composés présentent des propriétés phytotoxiques avant et après apparition des herbes et sont utiles en tant qu'herbicides séléctifs.
PCT/US1985/001786 1985-08-23 1985-09-19 Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione Ceased WO1987001699A1 (fr)

Priority Applications (11)

Application Number Priority Date Filing Date Title
JP60504287A JPS63500939A (ja) 1985-09-19 1985-09-19 ２―［１―（３―クロロアリルオキシイミノ）アルキル］―５―アルキルチオアルキル―シクロヘキサン―１，３―ジオン除草剤
GB8708127A GB2188321B (en) 1985-08-23 1985-09-19 2-[1-(3-trans-chloroallyloxyamino)propylidene]-5-(2-ethylthiopropyl)- cyclohexane-1,3-dione herbicides
HU854220A HU198605B (en) 1985-09-19 1985-09-19 Herbicides comprising 2-/1-(3-chloroallyloximino)-propyl/-5-(2-ethylthiopropyl)-cyclohexane-1,3-dione or salt thereof as active ingredient and process for producing the active ingredients
BR8507282A BR8507282A (pt) 1985-09-19 1985-09-19 Herbicidas 2-(1-(3-cloroaliloxiamino)alquilideno)-5-alquiltioalquil-ciclo-hexano-1,3-diona
KR1019860700645A KR920010518B1 (ko) 1985-08-23 1985-09-19 2-[1-(3-클로로알릴옥시아미노)알킬리덴]-5-알킬티오알킬-사이클로헥산-1,3-디온 제초제의 제조방법
RO142130A RO105610B1 (ro) 1985-08-23 1985-09-19 Procedeu de obtinere a 2-[1-(trans-cloraliloxiamino)-propiliden]-5-(2-etiltiopropil)-ciclohexan-1,3-dionei
NL8520309A NL193944C (nl) 1985-08-23 1985-09-19 Onkruidbestrijdingsmiddelen op basis van 2- 1-(3-chloorallyloxyamino)-alkylideen -5-alkylthioalkyl-1,3-cyclohexaandion.
SE8603868A SE458683B (sv) 1985-08-23 1986-09-15 2-(1-(3-trans-kloroallyloxiamino) propyliden)-5-(2-etyltiopropyl)cyklohexan-1,3-dion och foerenliga salter daerav, herbicida kompositioner innehaallande naemnda foerening, metoder att kontrollera graesartade plantor och graesarter daermed samt metod foer framstaellning daerav
RO124783A RO96716B1 (ro) 1985-09-19 1986-09-17 Compozitii de concentrat erbicid
NO86863733A NO162555C (no) 1985-08-23 1986-09-18 2-(1-(3-klorallyloxyamino)-alkyliden)-5-alkylthioalkyl-cyclohexan-1,3-dion-forbindelser, herbicide preparater inneholdende disse som aktive bestanddeler og anvendelse av forbindelsene for bekjempelse av gressvekster.
DK250087A DK164856C (da) 1985-09-19 1987-05-18 2-oe1-(3-chlorallyloxyamino)-alkyliden)-5-alkyl-thioalkylcyclohexanonforbindelser, fremgangsmaade til fremstilling deraf, herbicide kompositioner indeholdende forbindelserne samt en fremgangsmaade til bekaempelse af graesplanter under anvendelse af forbindelserne

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US76830185A 1985-08-23 1985-08-23
US79867085A 1985-11-15 1985-11-15

Publications (1)

Publication Number Publication Date
WO1987001699A1 true WO1987001699A1 (fr) 1987-03-26

Family

ID=27118040

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1985/001786 Ceased WO1987001699A1 (fr) 1985-08-23 1985-09-19 Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione

Country Status (14)

Country Link
EP (1) EP0236313A1 (fr)
KR (1) KR920010518B1 (fr)
CN (2) CN1021282C (fr)
AU (2) AU586200B2 (fr)
BE (1) BE903349A (fr)
CA (1) CA1271644A (fr)
CH (2) CH666890A5 (fr)
DE (1) DE3627410A1 (fr)
FR (1) FR2586416B1 (fr)
GB (2) GB2188321B (fr)
NL (2) NL193944C (fr)
NO (1) NO162555C (fr)
SE (1) SE458683B (fr)
WO (1) WO1987001699A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0349876A3 (en) * 1988-06-27 1990-01-24 Sumitomo Chemical Company, Limited Herbicidal composition
US5108488A (en) * 1989-07-21 1992-04-28 Valent U.S.A. Corporation Synergistic herbicidal composition
EP1296556B1 (fr) * 2000-07-03 2010-09-08 Valent U.S.A. Corporation Clethodime (-) optiquement pure, compositions et procedes permettant de commander la croissance des plantes a l'aide de cette clethodime
CN113024425A (zh) * 2019-12-24 2021-06-25 沈阳科创化学品有限公司 一种烯草酮的制备方法
US20230000078A1 (en) * 2019-02-20 2023-01-05 Valent U.S.A., Llc Clethodim compositions and methods of use thereof

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987001699A1 (fr) * 1985-08-23 1987-03-26 Chevron Research Company Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione
ATE52769T1 (de) * 1986-04-24 1990-06-15 Ciba Geigy Ag Acyl-cyclohexandione und deren oximaether mit herbizider und das pflanzenwachstum regulierender wirkung.
GB8722838D0 (en) * 1987-09-29 1987-11-04 Shell Int Research Oximino ether compounds
EP2321270B1 (fr) 2008-08-19 2016-03-23 Dow AgroSciences LLC Procédé perfectionné pour l'addition de thiolates à des composés carbonyle ou sulfonyle alpha, bêta-insaturés
CN105418470B (zh) * 2015-11-17 2017-12-15 江苏长青农化股份有限公司 一种烯草酮的合成方法
CN106187841B (zh) * 2016-07-08 2018-01-30 山东润博生物科技有限公司 一种烯草酮的工业化制备方法
CN112225682B (zh) * 2020-10-19 2022-02-25 中国科学院大连化学物理研究所 一种提高合成烯草酮反应速度的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440566A (en) * 1982-08-05 1984-04-03 Chevron Research Company Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU556148B2 (en) * 1982-01-29 1986-10-23 Ici Australia Limited Cyclohexane -1,3- dione derivatives
WO1987001699A1 (fr) * 1985-08-23 1987-03-26 Chevron Research Company Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440566A (en) * 1982-08-05 1984-04-03 Chevron Research Company Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0349876A3 (en) * 1988-06-27 1990-01-24 Sumitomo Chemical Company, Limited Herbicidal composition
US5108488A (en) * 1989-07-21 1992-04-28 Valent U.S.A. Corporation Synergistic herbicidal composition
EP1296556B1 (fr) * 2000-07-03 2010-09-08 Valent U.S.A. Corporation Clethodime (-) optiquement pure, compositions et procedes permettant de commander la croissance des plantes a l'aide de cette clethodime
US20230000078A1 (en) * 2019-02-20 2023-01-05 Valent U.S.A., Llc Clethodim compositions and methods of use thereof
US11839211B2 (en) * 2019-02-20 2023-12-12 Valent U.S.A., Llc Clethodim compositions and methods of use thereof
CN113024425A (zh) * 2019-12-24 2021-06-25 沈阳科创化学品有限公司 一种烯草酮的制备方法
CN113024425B (zh) * 2019-12-24 2022-05-17 沈阳科创化学品有限公司 一种烯草酮的制备方法

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AU5938086A (en) 1987-02-26
BE903349A (fr) 1986-04-01
NO863733L (no) 1987-03-26
GB2188321B (en) 1989-08-31
NO162555C (no) 1990-01-17
FR2586416B1 (fr) 1989-06-02
SE8603868D0 (sv) 1986-09-15
GB2188321A (en) 1987-09-30
CH667086A5 (de) 1988-09-15
CN1051285A (zh) 1991-05-15
GB2179352B (en) 1989-08-09
KR920010518B1 (ko) 1992-12-04
NL193944C (nl) 2001-03-02
NL8520309A (nl) 1985-09-19
KR870700287A (ko) 1987-12-28
GB2179352A (en) 1987-03-04
NL8601900A (nl) 1987-03-16
CH666890A5 (de) 1988-08-31
GB8708127D0 (en) 1987-05-13
CN1021282C (zh) 1993-06-23
AU586200B2 (en) 1989-07-06
AU585999B2 (en) 1989-06-29
AU4954185A (en) 1987-04-07
GB8620373D0 (en) 1986-10-01
SE8603868L (sv) 1987-03-20
NL193944B (nl) 2000-11-01
NO162555B (no) 1989-10-09
CA1271644A (fr) 1990-07-17
CN1011782B (zh) 1991-02-27
CN86105662A (zh) 1987-04-08
NO863733D0 (no) 1986-09-18
DE3627410A1 (de) 1987-02-26
FR2586416A1 (fr) 1987-02-27
SE458683B (sv) 1989-04-24
EP0236313A1 (fr) 1987-09-16

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