EP0593433A1 - Herbizide oxabicyclo-ätherverbindungen - Google Patents

Herbizide oxabicyclo-ätherverbindungen

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Publication number
EP0593433A1
EP0593433A1 EP90913636A EP90913636A EP0593433A1 EP 0593433 A1 EP0593433 A1 EP 0593433A1 EP 90913636 A EP90913636 A EP 90913636A EP 90913636 A EP90913636 A EP 90913636A EP 0593433 A1 EP0593433 A1 EP 0593433A1
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EP
European Patent Office
Prior art keywords
compound
growth
controlling
effective amount
undesired vegetation
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.)
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Application number
EP90913636A
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English (en)
French (fr)
Inventor
James Edward Powell, Jr.
Wendy Sue Richardson
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0593433A1 publication Critical patent/EP0593433A1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

Definitions

  • the present invention relates to novel oxabicyclo ether derivative compounds, to compositions containing these ether derivative compounds, and to methods of using these compounds or compositions to control the growth of undesired vegetation. More particularly, the present invention relates to a variety of compounds, compositions, and methods of using them which are herbicidally active on a wide variety of weed species and exhibit safety to rice, cereals and broadleaf crops.
  • the present invention comprises compounds of the formulas selected from the group consisting of:
  • X and Y are independently H or C(R 3 )(R 4 ) OR 5 ;
  • Z is C(R 3 )(R 4 ) OR 5 ;
  • R 1 is H or a straight-chain C 1 -C 3 alkyl
  • R 2 is H, C 1 -C 6 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, phenyl or C 1 -C 4 alkyl substituted by Ph, OH, CN, OR 8 , SO 2 R 8 , PhSO 2 , N 3 , CO 2 R 8 or CO 2 H;
  • R 3 , R 4 , R 9 and R 10 are independently H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl or C 1 -C 3 alkyl substituted with OCH 3 or OCH 2 CH 3 ;
  • R 5 is C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 3 -C 4
  • alkynyl benzyl or C 1 -C 4 alkyl substituted with OR 8 , OCF 3 ;
  • R 8 is C 1 -C 3 alkyl
  • W is phenyl optionally substituted with 1-3
  • alkylthio, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl, or W is a 5 or 6-membered heterocyclic ring containing 0-2 nitrogens, 0-2 oxygens or 0-2 sulfurs, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH 3 and OCH 3 ;
  • Z 1 is CH 2 , NR a , O, S or may be taken to form a double bond with an adjacent carbon;
  • R a is H or C 2 -C 3 alkyl;
  • R 6 is H, halogen, R 8 , OR 8 , SR 8 or CN;
  • R 7 is H, F, Cl, CH 3 , OCH 3 , OH or OR 8 ;
  • q 1 is 0, 1 or 2;
  • q 0, 1 or 2.
  • R 3 , R 4 , R 9 and R 10 each contains no more
  • heterocycles includes but is not limited to pyrrole, furan, thiophene,
  • Preferred compounds of the invention for either their biological activity or ease of synthesis are:
  • W is phenyl optionally substituted by 1-2
  • R a is H or C 2 -C 3 alkyl
  • R 5 is other than benzyl.
  • R 2 is H, C 1 -C 3 alkyl, C 2 -C 3 alkenyl or C 2 -C 3 alkynyl.
  • R 3 is H, C 1 -C 3 alkyl, C 3 -C 4 alkenyl or
  • R 4 is H, C 1 -C 3 alkyl, C 3 -C 4 alkenyl or
  • R 5 is H, C 1 -C 3 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl; R 5 s H, C 1 -C 3 alkyl, C 3 -C 4 alkenyl or
  • R 10 is H, C 1 -C 3 alkyl. C 3 -C 4 alkenyl or
  • Q is Q-1, Q-3, Q-6, Q-7 or Q-15.
  • Preferred 5 is the compound of Preferred 5 which is:
  • Compounds of Formula I-VIII that have the WCH 2 O group syn with respect to the oxygen-containing bridge are usually more herbicidally active than the anti form.
  • the present invention contemplates all of the herbicidally active forms resulting from
  • the compounds of the invention are prepared by treating the appropriately substituted oxabicycloalkanol (Ia-VIIIa) with a compound of the formula WCH 2 X in which X is a halogen atom or a mesyloxy, tosyloxy group or the like.
  • This reaction is carried out, as shown in Scheme 1, in the presence of a strong base, such as an alkali metal hydride, in an inert solvent, such as ethers, aromatic hydrocarbons, dimethyformamide and the like.
  • Suitable temperatures for the reaction are preferably from 20°C to 100°C.
  • the product ethers are recovered and isolated by conventional techniques.
  • compositions suitable for controlling the growth of undersired vegetation are also contemplated as within the scope of this invention. Such compounds are also contemplated as within the scope of this invention.
  • compositions comprise an effective amount of any of the compounds disclosed herein and at least one of the following: surfactant, solid, or liquid diluent.
  • Methods for controlling the growth of undesired vegetation are similarly considered to be within the scope of the invention. These methods comprise applying to the locus to be protected an effective amount of any of the compounds disclosed herein. Of particular importance is the method wherein the locus to be protected is rice.
  • the alkylating agents WCH 2 X are prepared in the conventional manners known to those skilled in the art from the alcohols WCH 2 OH.
  • the alcohols, WCH 2 OH are generally known in the art and are most conveniently prepared through metal hydride (e.g., sodium borohydride) reduction of the corresponding bicyclic ketones which can be derived by Friedel-Crafts type cyclization of
  • the compounds of Formulas I-VIII may be prepared by the coupling procedure described in Scheme 2, which is used in cases where the
  • This procedure uses a Lewis acidic metal oxide wherein the metal can remove the halide ion by forming an insoluble precipitate.
  • Silver (I) oxide can be used and the silver halide is the co-product.
  • Alternative metal oxides that may be used are HgO, CaO, MgO.
  • N,N-Dimethylformamide and ethereal solvents, such as diethyl ether, tetrahydrofuran, dioxane, or 1,2-dimethoxyethane are the preferred solvents.
  • Other solvents likely to provide good yields include dipolar aprotic solvents like dimethyl sulfoxide, acetone and
  • the oxabicycloalkanols (Ia-VIlla) can be obtained generally by one or more of the following routes: directly by a) epoxidation-cyclization of unsaturated cyclic alcohols, with or without
  • the compounds of Formula la are synthesized through the sequence shown in Scheme 3. Diels-Alder adducts are formed from readily available furans and from dienophiles including acrylate esters, acrolein, acryloyl chloride, and the like (see Murai et al., J. Chem. Soc. Chem. Comm. 221 (1981); and Kotsuki et al., Bull. Chem. Soc. Jpn., 57, 3339 (1984); and Laszlo et al., Tet. Let., 25. 4387 (1984) for
  • Diels-Alder adduct (2) is prepared from furan (3) and acryloyl chloride. Treatment of (2) with alcohol and base at 0°C to ambient temperature produces the corresponding ester. This intermediate is treated with the appropriate Grignard reagent or reducing agent (e.g, lithium aluminum hydride) as shown in Equation 3b. Optionally, treatment with an alkyl halide or alkyl sulfonate and a base (e.g., sodium hydride) in an inert solvent, such as tetrahydrofuran or N,N-dimethylformamide at ambient temperature to 150°C produces (4). Alcohol (4a) or ether (4b) is oxidized with a peroxide, such as hydrogen peroxide or m-chloroperbenzoic acid, in a suitable solvent, such as methylene chloride, to yield an epoxide.
  • a peroxide such as hydrogen peroxide or m-chloroperbenzoic acid
  • This intermediate is treated with a reducing agent, such as lithium triethylborohydride or lithium aluminum hydride, to reductively open the epoxide to produce alcohol la, using the method of Krishnamurthy et al., J. Amer. Chem. Soc., 95, 8486 (1973), as shown in Equation 3c. Scheme 3
  • a reducing agent such as lithium triethylborohydride or lithium aluminum hydride
  • Diels-Alder adducts (8) are treated with a peroxide as described in Equation 3c. This intermediate is treated with the appropriate Grignard reagent such as vinyl magnesium halide or allyl magnesium halide, to produce alcohol (9). Alcohol la can be prepared via the routes previously described in Equations 3b and 3c, or modifications thereof. Compounds of Formula la can also be synthesized through the sequence shown in Scheme 6. Diels-Alder adducts (10) are formed from furan (3) and a
  • Alcohol la can be prepared via the routes shown previously in Equations 4b and 4c or 5b and 5c or modifications thereof.
  • Cyclohexene (11) can be prepared via a Diels-Alder reaction using the methods of Alder et al., Chem. Ber., 86, 1312 (1953). Treatment of the diester with a Grignard reagent or a reducing agent yields the diol derivative. Monoalkylation, using methods described earlier, yield a mixture of ethers (12). Treatment of (12) with peroxide and acid, as taught in U.S. Patent Serial No. 4,542,244, yields alcohol Ila.
  • the endo form In situations where the endo form is desired, it can be obtained by oxidation of the 2-exo-IIa to the corresponding ketone, followed by reduction of the ketone with a reducing agent, such as sodium borohydride.
  • a reducing agent such as sodium borohydride.
  • Cyclohexene (13) can be prepared via a Diels-Alder from readily available dienophiles, such as maleic anhydride, and a diene component, such as isoprene or butadiene, using the methods of Fieser et al., J. Amer. Chem. Soc., 64, 802 (1942). Treatment of (13) with a Grignard reagent or reducing agent yields the diol derivative. Monoalkylation using methods described earlier yields ether (14).
  • the endo form In situations where the endo form is desired, it can be obtained by oxidation of the 2-exo-IIIa to the corresponding ketone, followed by reduction of the ketone with a reducing agent, such as sodium borohydride.
  • a reducing agent such as sodium borohydride.
  • Cyclohexene (15) can be prepared via a Diels-Alder from diene (16) and a readily available dienophile, such as methylacrylate. Treatment of (15) with a Grignard reagent or reducing agent yields the diol derivative. Monoalkylation using methods described earlier yields ether (17). Treatment of (17) with peroxide and acid, as described earlier, yields IlIa. In situations where the endo form is desired, it can be obtained by oxidation of the
  • Step A 7-oxabicyclo [2 .2 .1]hept-5-ene-2-carboxylic acid, 1,4-dimethyl-, methyl ester, (endo and exo, racemic)
  • Step B 7-oxabicyclo [2.2.1]hept-5-ene-2-methanol
  • 1,4-dimethyl-, exo-, (racemic-) Lithium aluminum hydride (2.3 g, 60.0 mmol) was added under a nitrogen atmosphere to 100 ml dry tetrahydrofuran. The mixture was heated at reflux for 15 minutes, then cooled to 0°C. A solution of 7-oxabicyclo [ 2 .2 .1]hept-5-ene-2-carboxylie acid, 1,4-dimethyl-, methyl ester, (exo, racemic) (14.3 g, 78.6 mmol) in 100 ml tetrahydrofuran was added dropwise over 1.5 hours. The mixture was then allowed to warm to ambient temperature and stirred for another 4.0 hours.
  • Step C 7-oxabicyclo[2.2.1]hept-2-ene, 1,4-dimethyl- 2-[(phenyl methoxy)methyl]-, (exo-, racemic)
  • Step D 3,8-dioxatricyclo[3.2.1.0 sup2, sup4]octane, l,5-dimethyl-6-[ (phenylmethoxy)methyl]-, (exo, racemic-)
  • Step E 7-oxabicyclo[2.2.1]heptan-2-ol, 1,4-dimethyl- 6-[ (phenyImethoxy)methyl]-, (exo, racemic), mixed with -5-[(phenylmethoxy)methyl]regioisomer
  • Step F 7-oxabicyclo [2.2.1]heptane, 1,4-dimethyl-2- (phenyImethoxy)-6-[(phenylmethoxy)methyl]-, 2:1 with the -5-[(phenylmethoxy)methyl]- isomer, (exo, exo, racemic)
  • Sodium hydride (0.39 g, 9.73 mmol) was washed with hexanes, decanted, and suspended in 10 ml of dimethylacetamide. To the suspension was added
  • Step A 7-oxabicyclo [2.2.1]hept-5-ene-2-carboxylic acid, methyl ester (exo and endo, racemic)
  • Step B 7-oxabicyclo [2.2.1]hept-5-ene, 2-(1-ethyl-1- methoxypropyl), exo-, (racemic-)
  • Step C 7-oxabicyclo[2.2.1]heptane, 2-(1-ethyl-1- methoxypropyl)-6-(phenyImethoxy)-, [exo-(2- alpha, 6-alpha)]
  • Step A cis-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dimethanol, (exo)- Furan (85.0 ml, 1.17 mol) was added to maleic anhydride (81.0 g, 0.827 mol) in 100 ml ether at ambient temperature. After 20 hours, the
  • Step B 7-oxabicyclo[2.2.1]heptane, 2,3-bis(ethoxy- methoxy)-5-hydroxy-, [2 exo-(2 alpha, 3 alpha, 5 alpha)]
  • Step C 7-oxabicyclo [2.2.1] heptane, 2,3-bis(ethoxymethoxy)-5-(phenyImethoxy)-, [2 exo-(2 alpha, 3 alpha, 5 alpha)]-
  • Step B ( ⁇ )-cis-4-methyl-4-eyelohexene-1,2-dimethanol To 300 ml of tetrahydrofuran at 0°C was added 16.0 g (0.42 mol) lithium aluminum hydride
  • Step C 2-endo,4-exo-( ⁇ )-4-hydroxy-5-methyl-6- oxabicyclo[3.2.1]octane-2-methanol
  • Step D ( ⁇ )-2-endo,4-exo-4-hydroxy-2-(methoxymethyl)- 5-methyl-6-oxabicyclo[3.2.1]octane
  • hexane-washed 60% sodium hydride 100 ml tetrahydrofuran.
  • THe reaction was cooled to 0°C and 6.1 g (0.035 mol) of ( ⁇ )-2-endo,4-exo-4-hydroxy-5-methyl-6-oxabicyclo-[3.2.1]octan-2-methanol in 70 ml tetrahydrofuran was added dropwise over 45 minutes keeping the
  • Step E ( ⁇ )-2-endo-2-(methoxymethyl)-5-methyl-6- oxabicyclo[3.2.1]octan-4-one
  • Step F ( ⁇ )-2-endo, 4-endo-4-hydroxy-2-(methoxymethyl)-5-methyl-6-oxabicyclo[3.2.1]octane
  • ⁇ 2-endo,4-endo-4-hydroxy-2-(methoxymethyl)-5-methyl-6-oxabicyclo[3.2.1]octan-4-one in tetrahydrofuran at -78°C was added a slight excess of 1 M lithium
  • Step A ( ⁇ )-diethyl 3,6-dihydro-4-methyl-2H- pyran-2,2-dicarboxylate
  • Step B ( ⁇ )-3,6-dihydro-4-methyl-2H-pyran-2,2- dimethanol
  • Step E ( ⁇ )-1-(ethoxymethyl)-5-methyl-2,6- dioxabicyclo[3.2.1]octan-4-one
  • Step A ( ⁇ )-exo,exo,exo- ⁇ -diethyl-5,6-bishydroxy- 7-oxabicyclo[2.2.1]heptane-2-methanol
  • Step B ( ⁇ )-exo, exo, exo- ⁇ , ⁇ -diethyl-6-[(2-fluorophenyl)methoxy]-5-hydroxy-7-oxabicyclo[2.2.1]heptane-2-methanol
  • Step C ( ⁇ )-exo,exo,exo-5-(1-ethyl-1-methoxypropyl)-3((2-fluorophenyl)methoxy)- 2-methoxy-7-oxabicyclo[2.2.1]heptane
  • Tables 1-5 present examples of species of the present invention. It is understood that these enumerated examples are merely representative of the range of species contemplated by the present
  • Tables 1-8 correspond to the Formulas I-VIII of the compounds of the present invention.
  • Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable
  • Sprayable formulations can be
  • compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of
  • Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
  • Emulsifiers Annual MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent
  • Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering.
  • Example B wettable Powder
  • the active ingredient is first sprayed onto the diatomaceous earth then, the ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in
  • the product is reblended before packaging.
  • a slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
  • the active ingredient and Atlox emulsifiers are dissolved in the solvent, filtered and packaged.
  • Atlox 3403F and 3404F are blends of anionic and ionic emulsifiers from ICII Americas, Inc.
  • the active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
  • the ingredients are blended and milled to pass through a 100 mesh screen.
  • This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material.
  • the fluidization and spraying are continued until granules of the desired size range are made.
  • the spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%.
  • the material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and
  • the active ingredient, solvent and emulsifiers are blended together. This solution is added to a mixture of the ethylene glycol and water with stirring.
  • the compound is added directly to the water with stirring to produce the solution, which may then be packaged for use.
  • the active ingredient is sprayed onto the
  • preemergence herbicides are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops such as alfalfa (Medicago sativa), barley (Hordeum vulgare), corn (zea mays), cotton (Gossypium hirsutum), rape (Brassica napus), rice (Oryza sativa), soybean (Glycine max), sugar beet (Beta vulgaris), and wheat (Triticum aestivum).
  • alfalfa Medicago sativa
  • barley Hydeum vulgare
  • corn zea mays
  • cotton Gossypium hirsutum
  • rape Brasse
  • rice Oryza sativa
  • soybean Glycine max
  • sugar beet Beta vulgaris
  • wheat Triticum aestivum
  • Grass and broadleaf weed species controlled include, but are not limited to, barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), crabgrass (Dioitaria spp.), foxtail (Setaria spp.), lambsquarters (Chenopodium spp.), teaweed (Sida spinosa), umbrella sedge (Cyperus difformis), and waterchestnut (Eleocharis spp.).
  • barnyardgrass Echinochloa crus-galli
  • blackgrass Alopecurus myosuroides
  • crabgrass Dioitaria spp.
  • foxtail Setaria spp.
  • lambsquarters Choenopodium spp.
  • teaweed Sida spinosa
  • umbrella sedge Cosmetic difformis
  • waterchestnut Eleocharis spp.
  • These compounds also have utility for weed control of selected vegetation in specified areas such as around storage tanks, parking lots, highways, and railways; in fallow crop areas; and in citrus and plantation crops such as banana, coffee, oil palm, and rubber. Alternatively, these compounds are useful to modify plant growth.
  • Rates of application for compounds of this invention are determined by a number of factors.
  • the subject compounds should be applied at rates from 0.01 to 20 kg/ha with a preferred rate range of 0.03 to 1 kg/ha. Although a small number of compounds show no herbicidal activity at the rates tested, it is anticipated these compounds have herbicidal activity at higher application rates. One skilled in the art can easily determine application rates necessary for the desired level of weed control.
  • Compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides, or fungicides.
  • the following list exemplifies some of the herbicides suitable for use in mixtures.
  • herbicides may be particularly useful for weed control.
  • fluoroglycarboxymethyl 5-[2-chloro-4-(tricofen fluoromethyl)phenoxy] -2-nitrobenzoate fluridone 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone fomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy]- N-(methylsulfonyl)-2-nitrobenzamide fosamine ethyl hydrogen (aminocarbonyl)- phosphate
  • barnyardgrass Echinochloa crus-galli
  • cheatgrass gromus secalinus
  • cockiebur xanthium
  • Croperus rotundus tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated plants and untreated controls were maintained in a
  • Plant response ratings are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Soybean 3 0 1 0 3 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 1 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 2 1 0 0 0 0 0 0 0 0 0 0 2 0 1 0 1 1
  • Morningglory 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0
  • Morningglory 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 1 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 2 3 0 1 0 0 0 0 0 0 0 0 1 0 0 1 1 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Soybean 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
  • Morningglory 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP90913636A 1989-09-11 1990-09-05 Herbizide oxabicyclo-ätherverbindungen Withdrawn EP0593433A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US43173489A 1989-09-11 1989-09-11
US431734 1989-09-11
PCT/US1990/004953 WO1991003464A1 (en) 1989-09-11 1990-09-05 Herbicidal oxabicyclo ethers

Publications (1)

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EP0593433A1 true EP0593433A1 (de) 1994-04-27

Family

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EP (1) EP0593433A1 (de)
JP (1) JPH05500063A (de)
AU (1) AU637406B2 (de)
CA (1) CA2065337A1 (de)
WO (1) WO1991003464A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR9205717A (pt) * 1991-01-30 1994-05-17 Du Pont Éteres biciclicos herbicidas
BR9206017A (pt) * 1991-05-20 1994-08-02 Du Pont Eteres oxatricÍclicos herbicidas
CN118005577A (zh) * 2022-11-09 2024-05-10 青岛清原化合物有限公司 一种氧杂双环烷类化合物及其制备方法、除草组合物和应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4670041A (en) * 1981-12-16 1987-06-02 E. I. Du Pont De Nemours And Company Oxabicycloalkane herbicides
US4486219A (en) * 1983-04-21 1984-12-04 Shell Oil Company 6-Oxabicyclo[3.2.1]octane derivatives and compositions and methods for controlling plant growth
KR950001023B1 (ko) * 1986-04-14 1995-02-07 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 할로겐화 헤테로시클릭 에테르 제초제 제조방법
US4798621A (en) * 1986-10-10 1989-01-17 E. I. Du Pont De Nemours And Company Selective method-of-use of oxabicycloalkanes
BR8807695A (pt) * 1987-09-15 1990-08-07 Du Pont Oxabicicloalcanos seletivos
KR900701793A (ko) * 1988-05-23 1990-12-04 제임스 제이. 플린 제초제 옥사비사이클로알칸 에테르
PT93107A (pt) * 1989-02-10 1990-08-31 Du Pont Processo para a preparacao de novos derivados etereos de oxabiciclononano com accao herbicida

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9103464A1 *

Also Published As

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CA2065337A1 (en) 1991-03-12
JPH05500063A (ja) 1993-01-14
AU637406B2 (en) 1993-05-27
AU6347490A (en) 1991-04-08
WO1991003464A1 (en) 1991-03-21

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