WO2000073277A1 - Composes tricycliques condenses, procede de preparation associe, et compositions d'herbicides contenant ces composes - Google Patents

Composes tricycliques condenses, procede de preparation associe, et compositions d'herbicides contenant ces composes Download PDF

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Publication number
WO2000073277A1
WO2000073277A1 PCT/US2000/008745 US0008745W WO0073277A1 WO 2000073277 A1 WO2000073277 A1 WO 2000073277A1 US 0008745 W US0008745 W US 0008745W WO 0073277 A1 WO0073277 A1 WO 0073277A1
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Prior art keywords
alkyl
halogen
methyl
aryl
amino
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PCT/US2000/008745
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English (en)
Inventor
Sandeep Gupta
David A. Pulman
Bai-Ping Ying
Masamitsu Tsukamoto
Takahiro Haga
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Ishihara Sangyo Kaisha, Ltd.
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Priority to US09/980,398 priority Critical patent/US6770596B1/en
Priority to AU46414/00A priority patent/AU4641400A/en
Publication of WO2000073277A1 publication Critical patent/WO2000073277A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/06—Peri-condensed systems

Definitions

  • the present invention relates to fused tricyclic compounds, process for their preparation, and herbicidal compositions containing them.
  • benzoxazine type compounds with a functional group introduced at position 5 followed by cyclization afford fused tricyclic compounds which exhibit herbicidal activity.
  • This invention delineates a method for the control of undesired vegetation in a plantation crop by the application to the locus of the crop an effective amount of a compound described herein.
  • the herbicidal compounds of the present invention are described by the following formula (I) or its salt:
  • Q is a heterocycle selected from the group consisting of Ql to Q24:
  • Ri is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, amino, alkoxyalkyl, acetyl, alkoxycarbonylamino, alkylcarbonylamino or alkoxycarbonyl;
  • R 2 is alkyl, haloalkyl, alkoxy, haloalkoxy or unsubstituted or substituted phenyl;
  • R 3 is hydrogen, halogen, nitro, amino, alkylamino, haloalkylamino, cyano or amide;
  • R and R 5 are independently oxygen, sulfur or imino; Q6, Q7, Q10, Q16 or Q17 may be unsaturated containing one or two double bonds in the 6-membered ring;
  • Y is hydrogen or halogen
  • A is -O-, -S-, -S(O)-, S(O) 2 , -NH-, -C(O)-, -C(S)-, -C(NH)- or -CR 6 R 7 -;
  • A' is -O-, -S-, -S(O)-, S(O) 2 , -NH-, -C(O)-, -C(S)-, -C(NH)- or -CRjoRn-; n is an integer of 0 to 2; m is an integer of 0 to 2;
  • B is N, CH, C, or N +
  • R 6 , R 7 , R 8 , R 9 , Rio, R ⁇ , R ⁇ 2 , R13, R14 and R 15 are independently hydrogen, halogen, hydroxy, cyano, nitro, amino, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, aryl, heteroaryl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonylamino, alkylaminocarbonylamino, arylaminocarbonylamino, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl, cycloalkoxycarbonylalkyl, alkylcarbonyloxyalkyl, alkylcarbonylaminoalkyl, alkoxyalkylcarbonylalkyl, heterocycloalkyl
  • R is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkoxycarbonylalkyl, alkoxyalkoxycarbonylalkyl, cycloalkoxycarbonylalkyl, aralkyl, heteroaralkyl, aryloxyalkyl or heteroaryloxyalkyl where any of these groups may be substituted with at least one substituent selected from the group consisting of halogen, cyano, nitro, amino, carboxyl, alkylthioalkyl, hydroxyalkyl, CON(R 16 )R I7 and COON(R 16 )R 17 ;
  • R ⁇ 6 and R ⁇ are independently hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl, cycloalkoxycarbonylalkyl, alkylcarbonyloxyalkyl, alkylcarbonylaminoalkyl, alkoxyalkylcarbonylalkyl, phenyl or benzyl where any of these groups may be substituted with at least one substituent selected from the group consisting of halogen, cyano, carboxyl, hydroxy, nitro and amino.
  • alkyl used either alone or in compound words such as haloalkyl or alkoxy indicates either straight chain or branched alkyls containing 1-8 carbon atoms.
  • Alkenyl and alkynyl include straight chain or branched alkenes and alkynes respectively containing 2-8 carbon atoms.
  • halogen either alone or in the compound words such as haloalkyl indicates fluorine, chlorine, bromine, or iodine.
  • a haloalkyl is represented by an alkyl partially or fully substituted with halogen atoms that may be same or different.
  • a cycloalkyl group implies a saturated or unsaturated carbocycle containing 3-8 carbon atoms.
  • a heterocycloalkyl group is a cycloalkyl group carrying 1 -4 heteroatoms which are representd by oxygen, nitrogen, or sulfur atoms.
  • An aryl group signifies an aromatic carbocycle containing 4-10 carbon atoms.
  • a heteroaryl group is an aromatic ring containing 1-4 heteroatoms which are represented by oxygen, nitrogen, or sulfur atoms, and may for example be furanyl, pyridyl, thienyl, pyrimidinyl, benzofuranyl, quinolyl, benzothienyl or quinoxalyl.
  • the compound of the formula (I) may form a salt with an acidic substance or a basic substance.
  • the salt with an acidic substance may be an inorganic acid salt such as a hydrochloride, a hydrobromide, a phosphate, a sulfate or a nitrate.
  • the salt with a basic substance may be a salt of an inorganic or organic base such as a sodium salt, a potassium salt, a calcium salt, a quarternary ammonium salt such as ammonium salt or a dimethylamine salt.
  • the compound of the formula (I) may exist as geometrical or optical isomers and the present invention includes all of these isomeric forms.
  • Q is Ql-5, Q16 or Q17;
  • Q is Ql or Q3; Y is fluorine; and R, R 6 , R , R ⁇ 2 and R ⁇ 3 are the same as defined above.
  • preferred compounds are as follows: 8-[l-Methyl-6-(trifluoromethyl)-2,4-(lH, 3H)-pyrimidinedione-3-yl]-9-fluoro- 5H-pyrazino[l,2,3-de]-l ,4-benzoxazine-3,6-(2H, 7H)-dione (1-1), 8-[4-Chloro-l-methyl- 5-(trifluoromethyl)-lH-pyrazol-3-yl]-9-fluoro-5H-pyrazino[l,2,3-de]-l,4-benzoxazine- 3,6(2H, 7H)-dione (1-13), 8-[4-Chloro-5-(difluoromethoxy)-l-methyl-lH-pyrazole-3-yl)- 9-fluoro-5H-pyrazino[l,2,3-de]-l,4-benzoxazine-3,6(2H)
  • the compound of the formula (I) can be produced, for example, by the following methods A to D:
  • the reactive derivative of R ⁇ 2 (R ⁇ 3 )C(Cl)COOH may, for example, be a compound selected from the group consisting of an alkyl halide, alkyl acid halide, aryl acid halide, alkyl acid anhydride, aryl acid anhydride, alkylhaloformate, alkyl isocyanate, aryl isocyanate, alkyl dihalide, aliphatic aldehyde, aliphatic ketone, aromatic aldehyde, and aromatic ketone.
  • the reaction is conducted usually in the presence of a solvent, if necessary, in the presence of a base.
  • the solvent may, for example, be an aromatic hydrocarbon such as benzene or toluene; an ether such as diethyl ether, tetrahydrofuran or dioxane; a halogenated hydrocarbon such as methylene chloride or chloroform; an aprotic polar solvent such as acetonitrile, dimethylformamide or pyridine.
  • the base may, for example, be a tertiary amine such as trimethylamine, triethylamine; a pyridine; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkali metal carbonate such as sodium carbonate or potassium carbonate; or an alkali metal alkoxide such as sodium methoxide or sodium ethoxide.
  • a tertiary amine such as trimethylamine, triethylamine
  • a pyridine an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide
  • an alkali metal carbonate such as sodium carbonate or potassium carbonate
  • an alkali metal alkoxide such as sodium methoxide or sodium ethoxide.
  • the reaction temperature is usually from 50° to +150°C, preferably from 0° to 100°C.
  • the reaction time is form 0.1 to 24 hours.
  • the cyclization reaction is carried out usually in a solvent under anhydrous conditions in the presence of a base.
  • the solvent may, for example, be an aromatic hydrocarbon such as benzene or toluene; an ether such as diethyl ether, tetrahydrofuran or dioxane; a halogenated hydrocarbon such as methylene chloride or chloroform; an aprotic polar solvent such as acetonitrile, dimethylformamide or pyridine.
  • the base may, for example, be a tertiary amine such as trimethylamine, triethylamine, N,N- diisopropylethylamine; a pyridine; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal alkoxide such as sodium methoxide or sodium ethoxide, or an alkali metal hydride such as sodium hydride or potassium hydride.
  • Alkali metal halides such as sodium iodide, potassium iodide may be used as catalysts.
  • nitric acid or fuming nitric acid which may be mixed with sulfuric acid or acetic acid.
  • the amount of nitric acid is usually from 1 to 100 moles per one mole of the compound of the formula (VIII).
  • the reaction temperature is usually from 0° to 100°C.
  • the reaction time is form 0.1 to 24 hours.
  • the above reduction reaction is carried out by treatment with iron in acetic acid or ethanolic hydrochloric acid, or by hydrogenation using palladium on carbon or platinum oxide as catalyst.
  • the reaction temperature is usually from 0° to 50°C.
  • the reaction time is from 0.1 to 24 hours.
  • the reaction for the formation of X from XI is carried out in a solvent such as dimethylsulfoxide, tetrahydrofuran, or dioxane in the presence of a base such as hydrazine.
  • a solvent such as dimethylsulfoxide, tetrahydrofuran, or dioxane
  • the reaction temperature is usually from 0° to 100°C.
  • the reaction time is from 0.1 to 24 hours.
  • EXAMPLE 8 Preparation of 7-Fluoro-6-[4-chloro-l-methyl-5-(trifluoromethyl)-lH- pyrazol-3-yl]-2-R-methyl-2H- 1 ,4-benzoxazine-3(4H)-one.
  • Methyl-2-R-[4-[4-chloro- 1 -methyl-5-(trifluoromethyl)- lH-pyrazol-3-yl]-5-fluoro- 2-nitrophenoxy]propanoate (6.0 g. 14.09 mmol) was dissolved in glacial acetic acid (140 ml) and reduced iron powder (3.94 g, 70.45 mmol) was added.
  • Table 4 lists some of the characterization data for a few representative compounds of this invention.
  • the compounds of the present invention exhibit excellent herbicidal effects when used as an active ingredient of a herbicide.
  • the herbicide can be used for a wide range of applications, for example on crop lands such as paddy fields, upland farms, orchards and mulberry fields, and non-crop lands such as forests, farm roads, playgrounds, and factory sites.
  • the application method may be suitably selected for soil treatment application and foliar application.
  • the compounds of the present invention are capable of controlling noxious weeds including grass (gramineae) such as barnyardgrass (Echinochloa crus-galli), large crabgrass (Digitaria sanguinalis), green foxtail (Setaria viridis), goosegrass (Eleusine indica L.), wild oat (Avena fatua L.), Johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), alexandergrass (Brachiaria plantaginea), paragrass (Panicum purpurascen), sprangletop (Leptochloa chinensis) and red sprangletop (Leptochloa panicea); sedges (or Cyperaceae) such as rice flatsedge (Cyperus iria L.), purple nutsedge (Cyperus rotundus L.), Japanese bulrush (Scirpus Juncoides), flatsedge (Cyperus serotinus), small-flower umbrella
  • a crop plant such as corn (Zea mays L.), soybean (Glycine max Merr.), cotton (Gossypium spp.), wheat (Triticum spp.), rice (Oryza sativa L.), barley (Hordeum vulgare L.), oat (Avena sativa L.), sorgo (Sorghum bicolor Moench), rape (Brassica napus L.), sunflower (Helianthus annuus L.), sugar beet (Beta vulgaris L.), sugar cane (Saccharum ojficinarum L.), Japanese lawngrass (Zoysia Japonica stend), peanut (Arachis hypogaea L.) or flax (Linum usitatissimum L.).
  • the active ingredients of this invention are formulated into herbicidal compositions by mixing herbicidally active amounts with inert ingredients known to the art to facilitate either the suspension, dissolution or emulsification of the active ingredient for the desired use.
  • the type of formulation prepared recognizes the facts that formulation, crop and use pattern all can influence the activity and utility of the active ingredient in a particular use.
  • the present herbicidal compounds may be formulated as water dispersible granules, granules for direct application to soils, water soluble concentrates, wettable powders, dusts, solutions, emulsifiable concentrates (EC), microemulsion, suspoemulsion, invert emulsion or other types of formulations, depending on the desired weed targets, crops and application methods.
  • herbicidal formulations may be applied to the target area (where suppression of unwanted vegetation is the objective) as dusts, granules or water or solvent diluted sprays. These formulation may contain as little as 0.1% to as much as 97% active ingredient by weight.
  • Dusts are admixtures of the active ingredient with finely ground materials such as clays (some examples include kaolin and montmorillonite clays), talc, granite dust or other organic or inorganic solids which act as dispersants and carriers for the active ingredient; these finely ground materials have an average particle size of less than 50 microns.
  • a typical dust formulation will contain 1 % active ingredient and 99% carrier.
  • Wettable powders are composed of finely ground particles which disperse rapidly in water or other spray carriers.
  • Typical carriers include kaolin clays, Fullers earth, silicas and other absorbent, wettable inorganic materials. Wettable powders can be prepared to contain from 1 to 90% active ingredient, depending on the desired use pattern and the absorbability of the carrier. Wettable powders typically contain wetting or dispersing agents to assist dispersion in water or other carriers.
  • Water dispersible granules are granulated solids that freely disperse when mixed in water. This formulation typically consists of the active ingredient (0.1% to 95% active ingredient), a wetting agent (1-15% by weight), a dispersing agent (1 to 15% by weight) and an inert carrier (1-95% by weight).
  • Water dispersible granules can be formed by mixing the ingredients intimately then adding a small amount of water on a rotating disc (said mechanism is commercially available) and collecting the agglomerated granules.
  • the mixture of ingredients may be mixed with an optimal amount of liquid (water or other liquid) and passed through an extruder (said mechanism is commercially available) equipped with passages which allow for the formation of small extruded granules.
  • the mixture of ingredients can be granulated using a high speed mixer (said mechanism is commercially available) by adding a small amount of liquid and mixing at high speeds to affect agglomeration.
  • the mixture of ingredients can be dispersed in water and dried by spraying the dispersion through a heated nozzle in a process known as spray drying (spray drying equipment is commercially available). After granulation the moisture content of granules is adjusted to an optimal level (generally less than 5%) and the product is sized to the desired mesh size.
  • spray drying spray drying equipment is commercially available.
  • Granules are granulated solids that do not disperse readily in water, but instead maintain their physical structure when applied to the soil using a dry granule applicator. These granulated solids may be made of clay, vegetable material such as corn cob grits, agglomerated silicas or other agglomerated organic or inorganic materials or compounds such as calcium sulfate.
  • the formulation typically consists of the active ingredient (1 to 20%) dispersed on or absorbed into the granule.
  • the granule may be produced by intimately mixing the active ingredient with the granules with or without a sticking agent to facilitate adhesion of the active ingredient to the granule surface, or by dissolving the active ingredient in a solvent, spraying the dissolved active ingredient and solvent onto the granule then drying to remove the solvent.
  • Granular formulations are useful where in- furrow or banded application is desired.
  • Emulsifiable concentrates are homogeneous liquids composed of a solvent or mixture of solvents such as xylenes, heavy aromatic naphthas, isophorone or other proprietary commercial compositions derived from petroleum distillates, the active ingredient and an emulsifying agent or agents.
  • a solvent or mixture of solvents such as xylenes, heavy aromatic naphthas, isophorone or other proprietary commercial compositions derived from petroleum distillates, the active ingredient and an emulsifying agent or agents.
  • the EC is added to water (or other spray carrier) and applied as a spray to the target area.
  • the composition of an EC formulation can contain 0.1% to 95% active ingredient, 5 to 95% solvent or solvent mixture and 1 to 20% emulsifying agent or mixture of emulsifying agents.
  • Suspension concentrate also known as flowable formulations are liquid formulations consisting of a finely ground suspension of the active ingredient in a carrier, typically water or a non-aqueous carrier such as an oil.
  • Suspension concentrates typically contain the active ingredient (5 to 50% by weight), carrier, wetting agent, dispersing agent, anti-freeze, viscosity modifiers and pH modifiers.
  • suspension concentrates are typically diluted with water and sprayed on the target area.
  • Solution concentrates are solutions of the active ingredient (1 to 70%) in solvents which have sufficient solvency to dissolve the desired amount of active ingredient. Because they are simple solutions without other inert ingredients such as wetting agents, additional additives are usually added to the spray tank mix before spraying to facilitate proper application.
  • Microemulsions are solutions consisting of the active ingredient (1 to 30%) dissolved in a surfactant or emulsifier, without any additional solvents. There are no additional solvents added to this formulation. Microemulsions are particularly useful when a low odor formulation is required such as in residential turfgrass applications.
  • Suspoemulsions are combinations of two active ingredients.
  • One active ingredient is made as a suspension concentrate (1-50% active ingredient) and the second active is made as a emulsifiable concentrate (0.1 to 20%).
  • a reason for making this kind of formulation is the inability to make an EC formulation of the first ingredient due to poor solubility in organic solvents.
  • the suspoemulsion formulation allows for the combination of the two active ingredients to be packaged in one container, thereby minimizing packaging waste and giving greater convenience to the product user.
  • the herbicidal compounds of this invention may be formulated or applied with insecticides, fungicides, acaricides, nematicides, fertilizers, plant growth regulators or other agricultural chemicals.
  • Certain tank mix additives such as spreader stickers, penetration aids, wetting agents, surfactants, emulsifiers, humectants and UV protectants may be added in amounts of 0.01% to 5% to enhance the biological activity, stability, wetting, spreading on foliage or uptake of the active ingredients on the target area or to improve the suspensibility, dispersion, redispersion, emulsifiability, UV stability or other physical or physico-chemical property of the active ingredient in the spray tank, spray system or target area.
  • compositions of the present invention may be used in admixture with or in combination with other agricultural chemicals, fertilizers, adjuvants, surfactants, emulsifiers, oils, polymers or phytotoxicity-reducing agents such as herbicide safeners. In such a case, they may exhibit even better effects or activities.
  • other agricultural chemicals herbicides, fungicides, antibiotics, plant hormones, plant growth regulators, insecticides, or acaricides may, for example, be mentioned.
  • herbicidal compositions having the compounds of the present invention used in admixture with or in combination with one or more active ingredients of other herbicides it is possible to improve the herbicidal activities, the range of application time(s) and the range of applicable weed types.
  • the compounds of the present invention and an active ingredient of another herbicide may be separately formulated so they may be mixed for use at the time of application, or both may be formulated together.
  • the present invention covers such herbicidal compositions.
  • the blend ratio of the compounds of the present invention with the active ingredient of other herbicides can not generally be defined, since it varies depending on the time and method of application, weather conditions, soil type and type of formulation.
  • one active ingredient of other herbicide may be incorporated usually in an amount of 0.01 to 100 parts by weight , per one part by weight of the compounds of the present invention.
  • the total dose of all of the active ingredients is usually from 1 to 10000 g/ha, preferably from 5 to 500 g/ha.
  • the present invention covers such herbicidal compositions.
  • Herbicidal compositions having the compounds of the present invention used in combination with other herbicides may occasionally exhibit a synergistic effect.
  • auxin activities of plants including a phenoxy acetic acid type such as 2,4-D, 2,4-DB, 2,4-DP, MCPA, MCPP, MCPB or naproanilide (including the free acids, esters or salts thereof), an aromatic carboxylic type such as 2,3,6 TBA, dicamba, dichlobenil, a pyridine type such as picloram (including free acids and salts thereof), triclopyr or clopyralid and others such as naptalam, benazolin, quinclorac, quinmerac or diflufenzopyr (BAS 654H).
  • a phenoxy acetic acid type such as 2,4-D, 2,4-DB, 2,4-DP, MCPA, MCPP, MCPB or naproanilide (including the free acids, esters or salts thereof)
  • an aromatic carboxylic type such as 2,3,6 TBA, dicamba, dichlobenil
  • a pyridine type such as picloram (including
  • urea type such as diuron, linuron, isoproturon, chlorotoluron, metobenzuron, tebuthiuron or fluometuron
  • a triazine type such as simazine , atrazine, cyanazine, terbuthylazine, atraton, hexazinone, metribuzin, simetryn, ametryn, prometryn, dimethametryn or triaziflam
  • a uracil type such as bromacil, terbacil or lenacil
  • an anilide type such as propanil or cypromid
  • carbamate type such as desmedipham or phenmedipham
  • a hydroxybenzonitrile type such as bromoxynil or ioxynil
  • others such as pyridate, bentazon and methazole.
  • a quaternary ammonium salt type such as paraquat, diquat or difenzoquat, which is believed to be converted to free radicals by itself to form active oxygen in the plant and thus to exhibit quick herbicidal effects.
  • photsensitizing substance including a diphenyl ether type such as nitrofen, lactofen, acifluorfen-sodium, oxyfluorfen, fomesafen, bifenox, or chlomethoxyfen, a cyclic imide type such as chlorphthalim, flumioxazin, cinidon-ethyl, or flumiclorac-pentyl, and others such as oxadiazon, sulfentrazone, thidiazimin, azafenidin, carfentrazone, isopropazole, fluthiacet-methyl, pentoxazone, pyrafluf en-ethyl and oxadiargyl.
  • a diphenyl ether type such as nitrofen, lactofen, acifluorfen-sodium, oxyfluorfen, fomesafen, bifenox, or chlomethoxyfen
  • carotenoids including a pyridazinone type such as norflurazon, chloridazon or metflurazon, a pyrazol type such as pyrazolate, pyrazoxyfen or benzofenap, and others such as fluridone, fluramone, diflufencam, methoxyphenone, clomazone, amitrole, s
  • aryloxyphenoxypropionic acid type such as diclofop-methyl, pyrofenop-sodium, fluazifop butyl or fluazifop-p-butyl, haloxyfop-methyl, quizalofop p-ethyl, quizalafop p-tefuryl, fenoxaprop ethyl or fenoxaprop-p-ethyl, flamprop-M-methyl or flamprop-m-isopropyl or cyhalofop-butyl and a cyclohexanedione type such as alloxydim-sodium, sethoxydim, clethodim, tepraloxydim or tralkoxydim.
  • an aryloxyphenoxypropionic acid type such as diclofop-methyl, pyrofenop-sodium, fluazifop butyl or fluazifop
  • sulfonylurea type such as chlorimuron-ethyl, nicosulfuron, metsulfuron-methyl, triasulfuron, primisulfuron, tribenuron-methyl, chlorosulfuron, bensulfuron-methyl, sulfometuron-methyl, prosulfuron, halosulfuron or halosulfuron-methyl, thifensulfuron-methyl, rimsulfuron, azimsulfuron, flazasulfuron, l-mazosulfuron, cyclosulfamuron, flupyrsulfuron, lodosulfuron, ethoxysulfuron, flucarbazone, sulfosulfuron, oxasulfuron a t ⁇ azolopy ⁇ midinesulfonamide type such as flumetsulam.
  • a sulfonylurea type such as chlorimuron-ethyl, nic
  • metosulam, chloransulam or chloransulam-methyl an lmidazolinone type such as imazapyr, imazethapyr, lmazaquin, imazamox, imazameth, imazamethabenz methyl, a py ⁇ midinesalicyhc acid type such as pyrthiobac-sodium, bispy ⁇ bac-sodium, py ⁇ minobac-methyl or py ⁇ benzoxim (LGC-40863), and others such as glyphosate, glyphosate-ammon m, glyphosate-isopropylamine or sulfosate.
  • an lmidazolinone type such as imazapyr, imazethapyr, lmazaquin, imazamox, imazameth, imazamethabenz methyl
  • a py ⁇ midinesalicyhc acid type such as pyrthiobac-sodium, bispy ⁇ bac-sodium,
  • Those which are believed to exhibit herbicidal effects by inhibiting cell division of plant cells including a dinitroaniline type such as trifluralin, oryzalin, nitrahn, pendamethalin, ethafluralin, benefm and prodiamine, an amide type such as bensulide, napronamide, and pronamide, a carbamate type such as propham, chlorpropham, barban, and asulam, an organophosphorous type such as amiprofos-methyl or butamifos and others such as DCPA and dithiopyr.
  • a dinitroaniline type such as trifluralin, oryzalin, nitrahn, pendamethalin, ethafluralin, benefm and prodiamine
  • an amide type such as bensulide, napronamide, and pronamide
  • a carbamate type such as propham, chlorpropham, barban, and asulam
  • chloroacetanilide type such as alachlor, metolachor
  • acetochlor including combinations with herbicide safeners such as dichlo ⁇ nid or MON 4660 or resolved isomeric mixtures of acetochlor containing safeners such as dichlormid or MON 4660
  • propisochlor or dimethenamid or an oxyacetamide type such as flufenacet.
  • Emulsifier 2.5 surfactant blend Toximul D-A Calcium sulfonate and nomonic Stepan Co.
  • Rhodopol 23 Xanthan gum Rhone-Poulenc Suspending Aid 0.25
  • a standard greenhouse herbicide activity screening system was used to evaluate the herbicidal efficacy and crop safety of these test compounds.
  • Seven broadleaf weed species including redroot pigweed (Amaranthus retroflexus, AMR), velvetleaf (Abutilon theophras ⁇ , ABT), sicklepod (Cassia obtusifolia, CAO), ivyleaf morningglory (Ipomoea hederacea, IPH), lambsquarters (Chenopodium album, CHA), common ragweed ( Ambrosia artemisiifolia L., AML), and cocklebur (Xanthium strumarium, XAS) were used as test species.
  • grass weed species including green foxtail (Setaria viridis, SEV), barnyardgrass (Echinochloa crus-galli, ECC), johnsongrass (Sorghum halepense, SOH), and large crabgrass (Digitaria sanguinalis, DIS) were also used.
  • field corn Zea mays L., var. Dekalb 535, CORN
  • soybean Glycine max L., var. Pella 86, SOY
  • upland rice Oryza sp., var.Tebonnet, RICE
  • wheat Triticum aestivum
  • test compounds were planted one day prior to application of the test compounds . All test compounds were dissolved in acetone and applied to the test pots in a volume of 187 1/ha. Test materials were applied at rates ranging from 8 g ai/ha to 1000 g ai/ha using a track sprayer equipped with a TJ8001E even flow flat fan spray nozzle. This application simulates a typical commercial field herbicide application.

Abstract

L'invention concerne des nouveaux composés tricycliques condensés représentés dans la formule (I). Q, Y, -L-X-, A, A', B, E, D, n et m sont tels que décrits dans la présente invention. En outre, l'invention concerne des procédés de fabrication de ces composés ainsi que des compositions, convenant à l'agriculture, contenant ces ingrédients actifs utiles comme herbicides pour la régulation générale ou sélective de pré-levée ou de postlevée d'espèces végétales indésirables.
PCT/US2000/008745 1999-06-02 2000-04-21 Composes tricycliques condenses, procede de preparation associe, et compositions d'herbicides contenant ces composes WO2000073277A1 (fr)

Priority Applications (2)

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US09/980,398 US6770596B1 (en) 2000-04-21 2000-04-21 Fused tricyclic compounds, process for their preparation, and herbicidal compositions containing them
AU46414/00A AU4641400A (en) 1999-06-02 2000-04-21 Fused tricyclic compounds, process for their preparation, and herbicidal compositions containing them

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US32382399A 1999-06-02 1999-06-02
US09/323,823 1999-06-02

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WO2000073277A1 true WO2000073277A1 (fr) 2000-12-07

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7998986B2 (en) 2001-12-21 2011-08-16 Exelixis Patent Company Llc Modulators of LXR
US8013001B2 (en) 2001-12-21 2011-09-06 Exelixis, Inc. Modulators of LXR

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0406993A2 (fr) * 1989-07-07 1991-01-09 Schering Aktiengesellschaft Dérivés de benzoxazolinone et benzoxazinone substituées, leur procédé de préparation et leur utilisation comme agent à activité herbicide
US5364856A (en) * 1991-03-28 1994-11-15 Eli Lilly And Company 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0406993A2 (fr) * 1989-07-07 1991-01-09 Schering Aktiengesellschaft Dérivés de benzoxazolinone et benzoxazinone substituées, leur procédé de préparation et leur utilisation comme agent à activité herbicide
US5364856A (en) * 1991-03-28 1994-11-15 Eli Lilly And Company 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles

Non-Patent Citations (1)

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Title
KOST A.N.: "Nitration of lilolidenes", AKAD. NAUK. LATV. SSR,, vol. 1, January 1996 (1996-01-01), pages 39 - 45, XP002930316 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7998986B2 (en) 2001-12-21 2011-08-16 Exelixis Patent Company Llc Modulators of LXR
US8013001B2 (en) 2001-12-21 2011-09-06 Exelixis, Inc. Modulators of LXR

Also Published As

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AU4641400A (en) 2000-12-18
AR039553A1 (es) 2005-02-23

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