WO1994003454A1 - Herbicidal triazinones - Google Patents
Herbicidal triazinones Download PDFInfo
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- WO1994003454A1 WO1994003454A1 PCT/US1993/006132 US9306132W WO9403454A1 WO 1994003454 A1 WO1994003454 A1 WO 1994003454A1 US 9306132 W US9306132 W US 9306132W WO 9403454 A1 WO9403454 A1 WO 9403454A1
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- Prior art keywords
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- haloalkyl
- halogen
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Classifications
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- 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 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 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 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
- R 1 is H, C 1 -C 8 alkyl (optionally substituted by
- halogen, CN, OH and/or C 1 -C 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 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxy, NO 2 and/or CF 3 ), or a heterocyclic hydrocarbon residue;
- R 2 , R 3 and R 4 are H, C 1 -C 6 alkyl (optionally
- 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 C 1 -C 4 alkyl, C 1 -C 4
- B is selected from the group C 1 -C 4 alkyl, C 2 -C 4
- haloalkyl C 3 -C 4 alkenyl and C 3 -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 2 CH 2 and
- Z is selected from the group CHR 22 , CH 2 CH 2 ,
- CR 22 CR 23 , NR 21 , O and S(O) 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 1 -C 3 alkyl and halogen
- R 5 is selected from the group H, C 1 -C 3 alkyl
- halogen C 1 -C 3 haloalkyl, cyclopropyl, C 2 alkenyl, C 2 alkynyl, CN, C(O)R 29 , CO 2 R 29 ,
- R 6 is selected from the group C 1 -C 6 alkyl, C 1 -C 8 haloalkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 alkenyl and
- R 7 is selected from the group C 1 -C 8 alkyl; C 3 -C 8 cycloalkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 1 -C 8 haloalkyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 alkoxyalkoxyalkyl;
- C 4 -C 8 haloalkynoxyalkyl C 6 -C 8 cycloalkylthioalkyl; C 4 -C 8 alkenylthioalkyl; C 4 -C 8 alkynylthioalkyl; C 1 -C 4 alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with a member selected from the group halogen, C 1 -C 3 alkyl and C 1 -C 3 haloalkyl; C 4 -C 8
- trialkylsilylalkyl C 3 -C 8 cyanoalkyl; C 3 -C 8 halocycloalkyl; C 3 -C 8 haloalkenyl; C 5 -C 8 alkoxyalkenyl; C 5 -C 8 haloalkoxyalkenyl; C 5 -C 8 alkylthioalkenyl; C 3 -C 8 haloalkynyl; C 5 -C 8 alkoxyalkynyl; C 5 -C 8 haloalkoxyalkynyl; C 5 -C 8 alkylthioalkynyl; C 2 -C 8 alkyl carbonyl; benzyl optionally substituted with a member selected from the group halogen, C 1 -C 3 alkyl and C 1 -C 3 haloalkyl; CHR 14 COR 8 ; CHR 14 P(O)(OR 8 ) 2 ;
- 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
- 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 1 -C 3 alkyl and C 1 -C 3 haloalkyl; R 9 and R 10 can be taken together as -(CH 2 ) 5 -,
- 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 4 alkyl and C 1 -C 4 haloalkyl;
- R 14 is selected from the group H and C 1 -C 4 alkyl
- R 16 is selected from the group C 1 -C 4 alkyl and C 1 -C 4 haloalkyl
- R 17 , R 18 , R 19 , R 20 , R 22 and R 23 are independently
- R 21 is selected from the group H, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;
- R 24 is selected from the group H and C 1 -C 4 alkyl
- R 25 is selected from the group H, C 1 -C 6 alkyl, C 3 -C 6 alkenyl and C 3 -C 6 alkynyl;
- R 26 is selected from the group H and C 1 -C 4 alkyl;
- R 27 is selected from the group C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, OCH 3 , SCH 3 , OCHF 2 , halogen, CN and NO 2 ;
- R 28 is selected from the group H, C 1 -C 4 alkyl and halogen
- R 29 , R 30 , R 31 and R 32 are independently selected
- R 33 is selected from the group H and C 1 -C 4 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 -C 6 alkynyl; and W is selected from the group O and S;
- R 7 is CHR 33 CO 2 R 34 or CO 2 R 34 then R 34 is other than C 2 haloalkyl; 3) when X is CHR 17 , Y is CHR 19 and Z is CHR 22 then at least one of R 17 , R 19 and R 22 is halogen;
- 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 CHFCl.
- Compounds of Formula I may exist as one or more stereoisomers.
- the various stereoisomers include enantiomers, diastereomers and geometric isomers.
- One skilled in the art will appreciate that one
- stereoisomer may be the more active.
- One skilled in the art knows how to separate said enantiomers, diastereomers and geometric isomers. Accordingly, the present invention comprises racemic mixtures,
- 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 2 is selected from the group H, C 1 -C 8 alkyl, Ci-Cs haloalkyl, halogen, OR 7 , S(O) n R 7 , COR 7 , CO 2 R 7 , C(O)SR 7 , C(O)NR 9 R 10 , CHO,
- R 5 is selected from the group H, C 1 -C 3 alkyl and halogen
- R 7 is selected from the group C 1 -C 8 alkyl; C 3 -C 8 cycloalkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 1 -C 8 haloalkyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 alkoxyalkoxyalkyl; C 4 -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 haloalkoxyalkyl;
- R 17 , R 19 , R 20 and R 22 are selected from the
- group H halogen and C 1 -C 4 alkyl; provided that only one of R 17 , R 19 , R 20 and R 22 is other than hydrogen .
- 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 CO 2 R 7 ;
- R 3 is selected from the group halogen and CN.
- Q is selected from the group Q-1, 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 C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 2 -C 4 alkoxyalkyl, C 1 -C 4 haloalkyl, C 3 -C 4 haloalkenyl and C 3 -C 4 haloalkynyl.
- X is CHR 17 ;
- Y is CHR 19 ;
- Z is CHR 22 .
- R 17 , R 19 , and R 22 are independently selected
- R 2 is selected from the group H, OR 7 , SR 7 and
- R 3 is selected from the group halogen and CN.
- Q is selected from the group Q-1, 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
- R 7 is selected from the group C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 2 -C 4 alkoxyalkyl,
- compounds of Formula I can be synthesized by reacting an ⁇ -ketoacid or ⁇ -ketoacid derivative of Formula II with a compound of
- thiosemicarbazide of Formula V cyclizing to form the heterocycle VI, and treating VI with an alkylating agent (R 16 -L, where L is a leaving group) in the presence of a base, or with a halogenating agent such as thionyl chloride, phosphorous oxychloride, or the like.
- an alkylating agent R 16 -L, where L is a leaving group
- a halogenating agent such as thionyl chloride, phosphorous oxychloride, or the like.
- 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 .
- reaction mixture was allowed to warm slowly to 0°C, then it was poured into a mixture of ice (300 g) and 1N aqueous hydrochloric acid (300 mL) and extracted into diethyl ether (200 mL, then 2 times with 100 mL). The combined organic layers were washed with water (200 mL), then brine (200 mL), then dried over MgSO 4 , filtered and the solvent removed under vacuum.
- Neat ⁇ -valerolactam (4.0 g, 40 mmol) was added to a suspension of trimethyloxonium tetrafluoroborate
- Step C 3-( 2 ,4-Dichlorophenyl)-6,7,8,9-tetrahydro-4H- pyrido[2,1-c][1,2,4]triazin-4(6H)-one
- Step B The product of Step B (1.24 g, 11 mmol) was dissolved in ethanol (5 mL), then 95% hydrazine
- 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. Flash chromatography yielded a residue, which was triturated with hexanes-chlorobutane to afford the title compound of Step C (0.17 g, 5.7%) as a light yellow powder, m.p. 119-123°C; 1 H NMR: ⁇ 1.9-2.2 (m,4H), 3.10 (t,2H), 3.99 (t,2H), 7.3-7.45 (m, 2H), 7.51 (d,1H).
- Step B 3-(2 ,4-Dichlorophenyl)-7,8,9,10- tetrahydro[1.2.4]triazino[4,3-a]-azepin-4(6H)- one
- Step A 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.
- Step B 3-(4-Chloro-2.5-difluorophenyl)-6,7,8,9- tetrahydro-4H-pyrido[2 ,1-c] [1 , 2 , 4 ]-triazin- 4(6H)-one
- Step A (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.
- the reaction mixture was filtered and solvent removed from the filtrate under vacuum. Flash chromatography yielded a residue, which was triturated with hexanes-chlorobutane to afford the title compound of Step B (1.01 g, 34%) as a pale yellow powder, m.p.
- Step B 3-(4-Chloro-2-fluorophenyl)-4H-pyrido-[2,1- C][1,2,4]-triazin-4(6H)-one
- Step C 3-(4-Chloro-2-fluorophenyl)-6,7,8,9-tetrahydro- 4H-pyrido[2,1-c][.2.4]-triazin-4(6H)-one
- the product of Step B (0.55 g, 2.0 mmol) was dissolved in acetic acid (30 mL), platinum oxide
- 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
- 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
- formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
- 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.
- Granules and pellets can be made by
- 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%.
- 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 hirsutum) , 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
- the compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides or fungicides.
- the following list is a list of commercial herbicides, insecticides or fungicides.
- 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,
- fluchloralin flumesulam, flumipropyn, fluometuron, fluorochloridone, fluorodifen, fluoroglycofen,
- mefenacet mefluidide, methalpropalin, methabenzthiazuron, metham, methazole, methoxuron, metolachlor, metribuzin, 1,2-dihydropyridazine-3,6-dione, molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid,
- napropamide naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate,
- pretilachlor primisulfuron, procyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynachlor,
- pyrazolate pyrazon, pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, rimsulfuron, secbumeton, sethoxydim, siduron, simazine, 1-(a,a-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor,
- nutsedge (Cyperus 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 (one to four leaf stage) for postemergence treatments.
- Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually
- 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.
- Chickweed 1 Chickweed 0
- Rate (1000 g/ha) 2 3 Rate (1000 g/ha) 2 3
- Morningglory 9 Morningglory 1 8
- Morningglory 4 9 8 Morningglory 0 10 7
- Rate (200 g/ha) 2 3 Rate (200 g/ha) 2 3
- Morningglory 6 9 Morningglory 0 3
- Rate 100 g/ha 4 5 Rate 100 g/ha 4 5
- Morningglory 9 Morningglory 4 5 Nutsedge 4 0 Nutsedge 0 0
- Rate (200 g/ha) 1 Rate (200 g/ha) 1
- Morningglory 7 Morningglory 4
- 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
- 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
- Morningglory 95 Morningglory 10 95
- Barley Igri 10 0 Barley Igri 0 0
- Giant foxtail 100 100 Giant foxtail 50 100
- Pigweed 100 100 Pigweed 70 100
- Rape 90 100 Rape 10 100
- Velvetleaf 100 100 Velvetleaf 100 95
- Wild buckwheat 100 100 Wild buckwheat 75 100
- Rate 31 g/ha 3 Rate 31 g/ha 3
- alfalfa Medicago sativa
- annual bluegrass Poa annua
- bermudagrass Ceynodon dactylon
- broadleaf signalgrass Brachiaria plantaginea
- dallisgrass Paspalum Dilatatum
- goosegrass Eleusine indica
- guineagrass Panicum maximum
- itchgrass RottboelIia exaltata
- johnsongrass (Sorghum halepense), large crabgrass (Digitaria sanguinalis) , peanuts (Arachis hypogaea) , pitted morningglory (Ipomoea lacunosa), purple nutsedge ( Cyperus rotundus), purslane (Portulaca oleracea) , ragweed (Ambrosia elatior) , sandbur ( Cenchrus
- echinatus echinatus
- smooth crabgrass Digitaria ischaemum
- Preemergence applications were made within one day of planting the seed or plant part. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm). Test chemicals were dissolved in a non-phytotoxic solvent and applied preemergence and postemergence to the plants. Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury 13 to 21 days after herbicide application. Plant response ratings, summarized in Table D, 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.
- Rate 125 g/ha 4 Rate 125 g/ha 4
- Alfalfa 0 Alfalfa 0
- Dallisgrass 0 Dallisgrass 0
- Peanuts 10 Peanuts 0 Pit Morninglory 0 Pit Morninglory 0
- 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'), blackgrass (Alopecurus myosuroides), chickweed
- Chickweed 0 Chickweed 0
- Green foxtail 0 Green foxtail 0
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU46536/93A AU4653693A (en) | 1992-07-29 | 1993-07-01 | Herbicidal triazinones |
EP93916806A EP0652876A1 (en) | 1992-07-29 | 1993-07-01 | Herbicidal triazinones |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US92182292A | 1992-07-29 | 1992-07-29 | |
US07/921,822 | 1992-07-29 | ||
US136993A | 1993-01-07 | 1993-01-07 | |
US08/001,369 | 1993-01-07 |
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WO1994003454A1 true WO1994003454A1 (en) | 1994-02-17 |
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PCT/US1993/006132 WO1994003454A1 (en) | 1992-07-29 | 1993-07-01 | Herbicidal triazinones |
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EP (1) | EP0652876A1 (en) |
AU (1) | AU4653693A (en) |
WO (1) | WO1994003454A1 (en) |
Cited By (10)
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WO1999059983A1 (en) * | 1998-05-20 | 1999-11-25 | Basf Aktiengesellschaft | Substituted 6-aryl-3-thioxo-5-(thi)oxo-2,3,4,5-tetrahydro-1,2,4-triazines |
WO2000008000A1 (en) * | 1998-08-08 | 2000-02-17 | Bayer Aktiengesellschaft | Use of substituted triazinones as herbicides |
US6060432A (en) * | 1995-10-25 | 2000-05-09 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
US7051565B2 (en) | 2000-06-09 | 2006-05-30 | Ex-Cell-O Gmbh | Cold forming machine |
JP2010508238A (en) * | 2006-04-10 | 2010-03-18 | シェーリング−プラウ・リミテッド | N-phenyl-1,1,1-trifluoromethanesulfonamide hydrazone derivative compounds and their use in the control of parasites |
WO2012041789A1 (en) * | 2010-10-01 | 2012-04-05 | Basf Se | Herbicidal benzoxazinones |
JP2012530098A (en) * | 2009-06-19 | 2012-11-29 | ビーエーエスエフ ソシエタス・ヨーロピア | Herbicidal benzoxazinones |
JP2013509379A (en) * | 2009-11-02 | 2013-03-14 | ビーエーエスエフ ソシエタス・ヨーロピア | Herbicide tetrahydrophthalimide |
US8916501B2 (en) | 2010-12-15 | 2014-12-23 | Basf Se | Herbicidal compositions |
CN107118168A (en) * | 2017-04-20 | 2017-09-01 | 福州大学 | A kind of method that copper catalysis synthesizes the triazineon compounds of trifluoromethyl 1,2,4 |
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FR1577658A (en) * | 1967-08-18 | 1969-08-08 | ||
DE3340026A1 (en) * | 1983-11-03 | 1985-05-15 | Schering AG, 1000 Berlin und 4709 Bergkamen | Triazinones, processes for the preparation of these compounds, and herbicidal agents containing them |
-
1993
- 1993-07-01 EP EP93916806A patent/EP0652876A1/en not_active Withdrawn
- 1993-07-01 AU AU46536/93A patent/AU4653693A/en not_active Abandoned
- 1993-07-01 WO PCT/US1993/006132 patent/WO1994003454A1/en not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1577658A (en) * | 1967-08-18 | 1969-08-08 | ||
DE3340026A1 (en) * | 1983-11-03 | 1985-05-15 | Schering AG, 1000 Berlin und 4709 Bergkamen | Triazinones, processes for the preparation of these compounds, and herbicidal agents containing them |
Cited By (17)
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US6060432A (en) * | 1995-10-25 | 2000-05-09 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
WO1999059983A1 (en) * | 1998-05-20 | 1999-11-25 | Basf Aktiengesellschaft | Substituted 6-aryl-3-thioxo-5-(thi)oxo-2,3,4,5-tetrahydro-1,2,4-triazines |
WO2000008000A1 (en) * | 1998-08-08 | 2000-02-17 | Bayer Aktiengesellschaft | Use of substituted triazinones as herbicides |
US7051565B2 (en) | 2000-06-09 | 2006-05-30 | Ex-Cell-O Gmbh | Cold forming machine |
JP2010508238A (en) * | 2006-04-10 | 2010-03-18 | シェーリング−プラウ・リミテッド | N-phenyl-1,1,1-trifluoromethanesulfonamide hydrazone derivative compounds and their use in the control of parasites |
US9066519B2 (en) | 2009-06-19 | 2015-06-30 | Basf Se | Herbicidal benzoxazinones |
JP2012530098A (en) * | 2009-06-19 | 2012-11-29 | ビーエーエスエフ ソシエタス・ヨーロピア | Herbicidal benzoxazinones |
US8754008B2 (en) | 2009-06-19 | 2014-06-17 | Basf Se | Herbicidal benzoxazinones |
US9220268B2 (en) | 2009-06-19 | 2015-12-29 | Basf Se | Herbicidal benzoxazinones |
JP2013509379A (en) * | 2009-11-02 | 2013-03-14 | ビーエーエスエフ ソシエタス・ヨーロピア | Herbicide tetrahydrophthalimide |
CN103221409A (en) * | 2010-10-01 | 2013-07-24 | 巴斯夫欧洲公司 | Herbicidal benzoxazinones |
US8669208B2 (en) | 2010-10-01 | 2014-03-11 | Basf Se | Herbicidal benzoxazinones |
WO2012041789A1 (en) * | 2010-10-01 | 2012-04-05 | Basf Se | Herbicidal benzoxazinones |
CN103221409B (en) * | 2010-10-01 | 2016-03-09 | 巴斯夫欧洲公司 | The benzo * zionoes of weeding |
US8916501B2 (en) | 2010-12-15 | 2014-12-23 | Basf Se | Herbicidal compositions |
CN107118168A (en) * | 2017-04-20 | 2017-09-01 | 福州大学 | A kind of method that copper catalysis synthesizes the triazineon compounds of trifluoromethyl 1,2,4 |
CN107118168B (en) * | 2017-04-20 | 2019-10-15 | 福州大学 | A kind of copper catalyzes and synthesizes Trifluoromethyl-1, the method for 2,4- triazineon compounds |
Also Published As
Publication number | Publication date |
---|---|
EP0652876A1 (en) | 1995-05-17 |
AU4653693A (en) | 1994-03-03 |
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