EP0652876A1 - Triazinones herbicides - Google Patents

Triazinones herbicides

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Publication number
EP0652876A1
EP0652876A1 EP93916806A EP93916806A EP0652876A1 EP 0652876 A1 EP0652876 A1 EP 0652876A1 EP 93916806 A EP93916806 A EP 93916806A EP 93916806 A EP93916806 A EP 93916806A EP 0652876 A1 EP0652876 A1 EP 0652876A1
Authority
EP
European Patent Office
Prior art keywords
group
alkyl
chr
haloalkyl
halogen
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.)
Withdrawn
Application number
EP93916806A
Other languages
German (de)
English (en)
Inventor
Eric Deguyon Taylor
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 EP0652876A1 publication Critical patent/EP0652876A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • 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
    • C07D487/04—Ortho-condensed systems

Definitions

  • This invention relates to certain substituted fused heterocyclic compounds which are useful as herbicides and their agriculturally suitable compositions as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant 0 growth regulants.
  • New compounds effective for controlling the growth of undesired vegetation are in constant demand.
  • such compounds are sought to selectively control the growth of weeds in useful crops 5 such as cotton, rice, corn, wheat, citrus and soybeans, to name a few.
  • Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer.
  • herbicides 0 are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these 5 purposes, but the search continues for products which are more effective, less costly and environmentally safe.
  • R-i is H, C -Cg alkyl (optionally substituted by halogen, CN, OH and/or ⁇ -0 4 alkoxy) , C 3 -C 8 cycloalkyl (optionally substituted by alkyl, halogen and/or phenyl) , an aromatic or aromatic-aliphatic residue (optionally substituted by C- L -C 4 alkyl, halogen, C !
  • R 2 , 3 and R are H, ⁇ -Cg alkyl (optionally substituted by halogen) or aryl (optionally substituted by ⁇ -Cg alkyl, halogen, C 3. -C 4 alkoxy, N0 2 and/or CF 3 ) .
  • This invention comprises novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergent and/or postemergent herbicides and/or plant growth regulants.
  • the compounds of Formula I are:
  • Q is selected from the group:
  • A is selected from the group ⁇ 4 alkyl, C 1 -C haloalkyl, C 2 -C alkenyl, C 2 -C 4 alkynyl, OR 16 ,
  • B is selected from the group ⁇ 4 alkyl, C 2 -C 4 haloalkyl, C3-C 4 alkenyl and C3-C 4 alkynyl; A and B can be taken together as X-Y-Z to form a fused ring such that X is connected to nitrogen and Z is connected to carbon; X is selected from the group CHR 17 , CH CH 2 and
  • CHR 19 CHR 20 , NR 21 , 0 and S(0) n ; Z is selected from the group CHR 22 , CH 2 CH 2 ,
  • CR 22 CR 23 , NR 21 , 0 and S(0) n ;
  • R 1 is halogen;
  • R 3 is selected from the group C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, OCH 3 , SCH 3 , OCHF 2 , halogen, CN and
  • R 4 is selected from the group H, C ⁇ - ⁇ alkyl and halogen
  • R 5 is selected from the group H, C 1 -C 3 alkyl, halogen, ⁇ - ⁇ haloalkyl, cyclopropyl, C 2 alkenyl, C 2 alkynyl, CN, C(0)R 29 , C0 2 R 29 , CONR 29 R 30 , CR 31 R 32 C(0)R 29 , CR 31 R 32 C0 2 R 29 ,
  • R 6 is selected from the group ⁇ -Cg alkyl, C ⁇ Cg haloalkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 alkenyl and
  • R 7 is selected from the group ⁇ -Cg alkyl; C 3 -C 8 cycloalkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; Ci-Cg haloalkyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkyl- thioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 alkoxyalkoxyalkyl;
  • R 8 is selected from the group C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl;
  • R 9 and R 11 are independently selected from the group H and C- -C ⁇ alkyl;
  • R 10 and R 12 are independently selected from the group C 1 -C 4 alkyl and phenyl optionally substituted with a member selected from the group halogen, C ⁇ - ⁇ alkyl and C x -C 3 haloalkyl;
  • R 9 and R 10 can be taken together as -(CH ) 5 -,
  • each ring optionally and independently substituted with one or more members selected from the group
  • R 11 and R 12 can be taken together with the carbon to which they are attached to form C 3 -C 8 cycloalkyl;
  • R 13 is selected from the group C 1 -C alkyl and C 1 -C 4 haloalkyl;
  • R 14 is selected from the group H and C -C 4 alkyl;
  • R 16 is selected from the group C 1 -C alkyl and C ⁇ - ⁇ haloalkyl;
  • R 17 , R 18 , R 19 , R 20 , R 22 and R 23 are independently selected from the group H, halogen, C 1 -C alkyl and C 1 -C haloalkyl;
  • R 21 is selected from the group H, C 2 -C 4 alkyl and c ⁇ c 4 haloalkyl;
  • R 24 is selected from the group H and C- - . ⁇ alkyl
  • R 25 is selected from the group H, Ci-Cg alkyl, C 3 -C 6 alkenyl and C 3 -Cg alkynyl
  • R 26 is selected from the group H and ( ⁇ 4 alkyl
  • R 27 is selected from the group ⁇ - ⁇ alkyl, C 2 -C 2 haloalkyl, OCH 3 , SCH 3 , OCHF 2 , halogen, CN and N0 2
  • R 28 is selected from the group H, ⁇ 4 alkyl and halogen
  • R 29 , R 30 , R 31 and R 32 are independently selected from the group H and C- L -C3 alkyl
  • R 33 is selected from the group H and C__-C_ alkyl
  • R 34 is selected from the group C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -
  • R 2 is OR 7 and R 7 is C 3 -C 8 alkynyl.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
  • Alkoxy includes methoxy, ethoxy, n-propyloxy, isopropyloxy, the different butoxy isomers, etc.
  • Alkenyl and alkynyl include straight chain or branched alkenes and alkynes, e.g.,
  • Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • halogen either alone or in compound words such as “haloalkyl”, means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl” said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFC1.
  • Compounds of Formula I may exist as one or more stereoisomers .
  • the various stereoisomers include enantiomers, diastereomers and geometric isomers.
  • one stereoisomer may be the more active.
  • the present invention comprises racemic mixtures, individual stereoisomers, and optically active mixtures. Preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are:
  • X is CHR 17 or CH 2 CH 2 ;
  • Y is CHR 19 or CHR 19 CHR 20 ;
  • Z is CHR 22 or CH 2 CH 2 ;
  • R 5 is selected from the group H, C 1 -C 3 alkyl and halogen
  • R 7 is selected from the group C-L-CS alkyl; C 3 -C f cycloalkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C- ⁇ -C Q haloalkyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C -C 8 alkoxy- alkoxyalkyl; C -C 8 cycloalkylalkyl; C 4 -C 8 alkenoxyalkyl; C 4 -C 8 alkynoxyalkyl; C 6 -C 8 cycloalkoxyalkyl; C 4 -C 8 alkenyloxyalkyl; C 4 -C 8 alkynyloxyalkyl; C 3 -C 8 haloalkoxy- alkyl;
  • R 17 , R 19 , R 20 and R 22 are selected from the group H, halogen and 0 -0 alkyl; provided that only one of R 17 , R 19 , R 20 and R 22 is other than hydrogen. 2) Compounds of Formula I wherein X is CHR 17 ; Y is CHR 19 CHR 20 ; Z is CHR 22 .
  • R 2 is selected from the group H, OR 7 , SR 7 and C0 2 R 7 ;
  • R 3 is selected from the group halogen and CN.
  • Q is selected from the group Q-l, Q-2, Q-4 and
  • a and B are taken together as X-Y-Z;
  • R 17 , R 18 , R 19 , R 20 , R 22 and R 23 are independently selected from the group H and F;
  • R 7 is selected from the group 0 -0 4 alkyl, C 3 -C 4 alkenyl, C3-C 4 alkynyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkyl, C3-C 4 haloalkenyl and C 3 -C 4 haloalkynyl .
  • R 17 , R 19 , and R 22 are independently selected from the group H, F, CH 3 and CF 3 .
  • R 3 is selected from the group halogen and CN.
  • Q is selected from the group Q-l, Q-2, Q-4 and Q-5;
  • a and B are taken together as X-Y-Z;
  • R 17 , R 19 , and R 22 are independently selected from the group H and F;
  • R 7 is selected from the group C 2 -C alkyl, C3-C 4 alkenyl, C 3 -C alkynyl, C 2 -C alkoxyalkyl,
  • compounds of Formula I can be synthesized by reacting an ⁇ -ketoacid or ⁇ -ketoacid derivative of Formula II with a compound of Formula Ilia or Formula Illb, which are amidrazones or are formally derivatives of semicarbazides or thiosemicarbazides .
  • Compounds of Formula Ilia and Illb are generally known in the art and can either be isolated or prepared in situ, as described in Justus Liebigs Ann . Chem . 755, 101 (1972), or in a similar manner.
  • R 16 -L where L is a leaving group
  • a transition metal catalyst such as platinum oxide
  • MCPBA meta-chloroperoxybenzoic acid
  • aryl halides QG can be synthesized via diazotization of known arylamines using conditions such as those described by Furniss, et al. in "Vogel's Textbook of Practical Organic Chemistry", Fifth Edition, Longman Scientific and Technical, Essex, England, pp 922-946. Iodine can also be incorporated into aromatic molecules by other known methods such as those described in Synthesis 1988, 923.
  • the triflates QG can be prepared from the corresponding phenols QOH by known methods. If required, ⁇ -ketoesters and ⁇ -ketoacids II can be interconverted by methods that will be apparent to one skilled in the art.
  • trifluoromethanesulfonates Ic can be converted to esters, thioesters, amides, and aldehydes Id by reaction with carbon monoxide and a nucleophile (Nuc) under conditions such as those described in Chem . Comm . 1987, 904, to alkenes Ie by reaction with an alkene under conditions such as those described in Heterocycles 26, 355 (1987), to ketones If by reaction with enol ethers under conditions such as those described in J. Org. Chem .
  • Step A Flash chromatography afforded the title compound of Step A (11.04 g, 44.7%) as an oil; 1 H NMR: ⁇ 1.40 (t,3H), 4.42 (q,2H), 7.39 (d,lH), 7.48 (s,lH), 7.73 (d,lH); IR (inter alia) : 1736, 1698 cm" 1 .
  • Step B 2.3.4.5-Tetrahydro-6-methoxypyridine
  • Neat 5-valerolactam (4.0 g, 40 mmol) was added to a suspension of trimethyloxonium tetrafluoroborate
  • Step C 3- ( 2 r -Dichlorophenyl1-6.7.8.9-tetrahydro-4H- pyridor2.1-cl r1.2.41 riazin-4 (6H -one
  • the product of Step B (1.24 g, 11 mmol) was dissolved in ethanol (5 mL) , then 95% hydrazine (0.33 mL, 10 mmol) was added and the solution was stirred 2 hours at room temperature.
  • the product of Step A (2.47 g, 10 mmol) dissolved in ethanol (1 mL) was added to the solution and the mixture was stirred overnight at room temperature. The reaction mixture was filtered and solvent removed from the filtrate under vacuum.
  • Step B 3- (2 .4-Dichlorophenyl)-7.8.9.10- tetrahydror1.2.41triazino ⁇ A.3-al-azepin-4 (6H)- one
  • the product of Step A (1.40 g, 9.8 mmol) was dissolved in ethanol (5 mL) , then 95% hydrazine (0.30 mL, 9.1 mmol) was added and the solution stirred 2 h at room temperature.
  • the product of Step A of Synthesis Example 1 (2.47 g, 10 mmol), dissolved in ethanol (5 mL) , was added to the solution and the mixture was stirred overnight at room temperature. Solvents were removed under vacuum.
  • Step B 3-(4-Chloro-2.5-difluorophenyl)-6, 7.8 r 9- tetrahydro-4H-pyrid ⁇ , l-cl l , 2 , 4 ]-triazin- 4 (6H)-one
  • the product of Step B of Synthesis Example 1 (1.24 g, 11 mmol) was dissolved in methanol (5 mL) , then 95% hydrazine (0.33 mL, 10 mmol) was added and the solution was stirred 2 h at room temperature.
  • the product of Step A (2.58 g, 11 mmol) of Example 3 was added to the solution and the mixture was stirred overnight at room temperature.
  • Step B 3-(4-Chloro-2-fluorophenyl)-4H-pyrido-r2.1- Cl ri.2.41-triazin-4 (6H)-one
  • Step B The residue was dissolved in 1,2-dichlorobenzene (12 mL) and the mixture was heated at reflux overnight, then volatiles were removed under vacuum. Flash chromatography yielded a residue, which was triturated with hexanes-chlorobutane to afford the title compound of Step B (0.78 g, 42%) as a tan powder, m.p. 209-211°C; ⁇ NMR: ⁇ 7.2-7.35 (m, 3H) , 7.71 (t, IH) , 7.86 (t, IH) , 7.96 (d, IH) , 8.95 (d, IH) .
  • Step C 3-(4-Chloro-2-fluorophenyl)-6 f 7,8,9-tetrahydro- 4H-pyridor2.1-cl ⁇ .2.41-triazin-4 (6H)-one
  • the product of Step B (0.55 g, 2.0 mmol) was dissolved in acetic acid (30 mL) , platinum oxide (25 mg, 0.11 mmol) was added and the mixture was treated with hydrogen gas (2.8 x 10 5 - 3.4 x 10 5 Pa) for 1.5 h.
  • An additional quantity of platinum oxide (25 mg, 0.11 mmol) was added and the mixture was treated with hydrogen gas (2.8 x 10 5 - 3.4 x 10 5 Pa) overnight.
  • the mixture was filtered, then volatiles were removed under vacuum.
  • Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • Use formulations include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.
  • compositions Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents and solvents are described in arsden, Solvents Guide, 2Nd Ed., Interscience, New
  • Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill.
  • Water-dispersible granules can be produced be agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., (1988), pp 251-259.
  • Suspensions are prepared by wet-milling; see, for example, U.S. 3,060,084.
  • Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4,
  • Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.
  • Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
  • Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Example C Granule Compound 1 10.0% attapulgite granules (low volative matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
  • Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • the compounds of the present invention are active postemergence and preemergence herbicides.
  • Several compounds of this invention are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops such as, but not limited to, corn ( Zea mays) , cotton ( Gossypium hirsutu ) , rice ( Oryza sativa) , soybean ( Glycine max) , wheat ⁇ Tritium aestivum) , barley (Hordeum vulgare) and plantation crops.
  • compounds of this invention can be used in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highways and railroad structures and in fence rows.
  • effective application rates for the compounds of this invention are 0.001 to 20 kg/ha with a preferred rate range of 0.004 to 0.25 kg/ha.
  • Effective rates of application for this invention are determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. One skilled in the art can select the effective rates for a given situation.
  • the 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.
  • a combination of a compound from this invention with one or more of the following herbicides may be particularly useful for weed control in plantation crops.
  • Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides.
  • a mixture of one or more of the following herbicides with a compound of this invention can be particularly useful for weed control: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benefin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid,
  • Plant response ratings summarized in Table A, 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.
  • Plants ranged in height from two to eighteen cm and were in the two to three leaf stage for the postemergence treatment.
  • Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury.
  • Plant response ratings, summarized in Table B, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results.
  • preemergence application to water that covered the soil surface (flood application) , and to plants that were in the one-to-four leaf stage (postemergence application) .
  • a sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.
  • Plant species in the preemergence and postemergence tests consisted of barley ⁇ Hordeum vulgare) , bedstraw ⁇ Galium aparine) , blackgrass ⁇ Alopecurus myosuroides) , chickweed ⁇ Stellaria media) , corn ⁇ Zea mays) , cotton ⁇ Gossypium hirsutum) , crabgrass ⁇ Digitaria sanguinalis) , downy brome ⁇ Bromus tectorum) , giant foxtail ⁇ Setaria faberii) , lambsquarters ⁇ Chenopodium album) , morningglory ⁇ Ipomoea hederacea) , pigweed ⁇ Amaranthusretroflexus) , rape ⁇ Brassica napus) , ryegrass ⁇ Lolium multiflorum) , sorghum ⁇ Sorghum bicolor) , soybean ⁇ Glycine max) , speedwell ⁇ Veronica persica) , sugar be
  • Plant species in the flood test consisted of rice (Oryza sativa) , umbrella sedge ( Cyperus difformis) , duck salad (Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli ) grown to the 1 and 2 leaf stage for testing. All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response ratings, summarized in Table C, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
  • alfalfa Medicago sativa
  • annual bluegrass Pieris annua
  • Plant response ratings are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response means no test result.
  • Test compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to-four leaf stage (postemergence application) .
  • a sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test.
  • Test compounds were applied within approximately one day after planting seeds for the preemergence test.
  • Crop and weed species include winter barley (Hordeum vulgare cv. 'Igri 1 ), blackgrass (Alopecurus myosuroides) , chickweed (Stellaria media) , downy brome (Bromus tectorum) , field violet (Viola arvensis) , galium (Galium aparine) , green foxtail (Setaria viridis) , kochia (Kochia scoparia) , lambsquarters (Chenopodium album) , speedwell (Veronica persica) , rape (Brassica napus) , ryegrass (Lolium multiflorum) , sugar beet (Beta vulgaris cv.
  • Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table E, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result.

Abstract

Triazinones substituées de la formule (I) dans laquelle Q est choisi dans le groupe Q-1, Q-2, Q-3, Q-4, Q-5 et Q-6; A est choisi parmi alkyle, haloalkyle, alcényle, alcynyle, OR16 SR16 et halogène; B est choisi parmi alkyle, haloalkyle, alcényle et alcynyle; A et B peuvent être pris ensemble en tant que X-Y-Z pour former une combinaison cyclique condensée de telle sorte que X soit lié à de l'azote et Z soit lié à du carbone; X est choisi dans le groupe CHR17, CH2CH2 et CR17=CR18; Y est choisi dans le groupe CHR?19, CR19=CR20, CHR19CHR20; NR21¿, O et S(O)¿n?; n est 0, 1 ou 2 et R?1¿ est halogène. Lesdits triazinones sont utiles en tant qu'herbicides et/ou régulateurs de la croissance des plantes.
EP93916806A 1992-07-29 1993-07-01 Triazinones herbicides Withdrawn EP0652876A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US92182292A 1992-07-29 1992-07-29
US921822 1992-07-29
US136993A 1993-01-07 1993-01-07
US1369 1993-01-07
PCT/US1993/006132 WO1994003454A1 (fr) 1992-07-29 1993-07-01 Triazinones herbicides

Publications (1)

Publication Number Publication Date
EP0652876A1 true EP0652876A1 (fr) 1995-05-17

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Country Status (3)

Country Link
EP (1) EP0652876A1 (fr)
AU (1) AU4653693A (fr)
WO (1) WO1994003454A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0862571B1 (fr) * 1995-10-25 2003-01-15 Degussa AG Sulfonamides herbicides
AU4362999A (en) * 1998-05-20 1999-12-06 Basf Aktiengesellschaft Substituted 6-aryl-3-thioxo-5-(thi)oxo-2,3,4,5-tetrahydro-1, 2,4-triazines
DE19835943A1 (de) * 1998-08-08 2000-02-10 Bayer Ag Substituierte Triazinone
DE10028165A1 (de) 2000-06-09 2001-12-13 Ex Cell O Gmbh Kaltwalzmaschine
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