CN1032005A - Weedicide - Google Patents
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- CN1032005A CN1032005A CN87105742A CN87105742A CN1032005A CN 1032005 A CN1032005 A CN 1032005A CN 87105742 A CN87105742 A CN 87105742A CN 87105742 A CN87105742 A CN 87105742A CN 1032005 A CN1032005 A CN 1032005A
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Herbicidal compound, for encircling substituted aryloxy phenoxy group triazolone, for example structural formula is:
Compound, R wherein
2For, C for example
2H
5OCO-CH (CH
3)-O-or CH
3SO
2-NH-CO-CH (CH
3)-O-.
Description
The present invention relates to control the undesired plants growth, as the new weedicide of control weeds in the field of narrow leaf and width leaf weed at agricultural, gardening and other.This data also relates to the intermediate for this weedicide of preparation.
An effective especially aspect of the present invention relates to structural formula and is:
Herbicidal compound, wherein Q-Ar-be a kind of replacement phenyl group (for example, structural formula is:
Wherein substituting group Q is in No. 5 positions (on position nitrogen between described structural formula I); Q is:
Z can be O, S, NH or alkylamino (as low-grade alkyl amino, for example methylamino-).
R
4Can be H or CH
3, and R
3Can be OH, alkoxyl group (for example lower alkoxy such as methoxy or ethoxy), rudimentary alkenyloxy or alkynyloxy group (for example allyloxy or alkynes propoxy-), amino, virtue amino (for example phenyl amino), alkylamino (low-grade alkyl amino for example, as methylamino-or dimethylamino), alkenyl amino (for example diallyl amino), alkoxy amino (lower alkoxy amino for example, as methoxyl group amino) or alkyl-, haloalkyl-or structural formula be-NHSO
2R
5Or-N(SO
2R
5) SO
2R
6Arlysulfonylamino.
R
5And R
6Can be independently alkyl (low alkyl group for example, as methyl, ethyl or propyl group), haloalkyl (for example junior alkyl halides, as trifluoromethyl) or aryl, as the phenyl of phenyl or replacement, (for example, phenyl alkoxyl group-replacement and/or halo-replacement).
" n " can be 1 or 2, and " m " can be 0 or 1.
R
1Can be H, alkyl (for example low alkyl group, as methyl), halogen, as Cl, Br or F, (low-grade halogenated alkyl for example is as CF for haloalkyl
3, CH
2F or CHF
2), nitro, NH
2, lower alkoxy or alkylthio (OCH for example
3Or SCH
3) or cyano group.Many R are arranged on same phenyl ring
1Substituting group.
In the structural formula I, (carrying out) selects R in the above
aAnd R
b, making when Q is methoxyl group or alkynes propoxy-(Q of the structural formula that replacement provides above having), compound is a kind of weedicide.For convenience's sake, be the Q in the structural formula I compound of methoxyl group or alkynes propoxy-here, be referred to as the methoxyl group analogue and the alkynes propoxy-analogue of the new compound of being applied for.This methoxyl group analogue and alkynes propoxy-analogue are many in this field usedly to be known.For example, the compound 1-7 of this application, the methoxyl group analogue of 26-72 and 88-91 (referring to tabulating 1 down) is the compound 1-(4-chloro-2-fluoro-5-p-methoxy-phenyl in the embodiment 1D of the world (patent) of announcement on October 10th, 1985 application WO85/04307)-3-methyl-4-difluoromethyl-△
2-1,2,4-triazoline-5-ketone, and the described 1-7 that is numbered, the alkynes propoxy-analogue of the compound of 26-72 and 88-91 is the compound among the embodiment 2 of the same world (patent) application, and compound 82 and 92 methoxyl group and alkynes propoxy-analogue simultaneously are as United States Patent (USP) 4, described in 398,943.
Substituent R on triazol inone ring
aAnd R
bFor this reason in the field known any one.For example, each can be independently low alkyl group or low-grade halogenated alkyl (for example fluoroalkyl); R
aAnd R
bSubstituent some embodiment is shown in Table 1.
" Ar " has a kind of substituting group (just not being H) on No. 2 positions of phenyl group or No. 4 positions, being preferably on No. 2 positions and No. 4 positions all has.
X can be H, and halogen, as Cl, Br or F(are preferably F), alkyl (for example, low alkyl group such as methyl), (low-grade halogenated alkyl for example is as CF for haloalkyl
3, CH
2F or CHF
2) or nitro; And
Y can be H, and halogen, as Cl, Br or F(are preferably Br or Cl), alkyl (for example, low alkyl group such as methyl), alkoxyl group (for example, lower alkoxy such as methoxyl group), the halogen hazel ɡ stifled shellfish hazel silk ribbon attached to an official seal or a medal hazel SOCF of figure that relaxes
3Or halogenated lower alkoxy is as-OCHF
2X preferably at present, the Y substituting group is: 2-F, 4-Cl; 2-F, 4-Br; 2,4-Cl; 2-Br, 4-Cl; And 2F, 4-CF
3
A major aspect of the present invention relates to structural formula and is:
Herbicidal compound, wherein Q ' (generally including Q) is:
R wherein
2Can be H, halogen (as Cl, Br or F), alkyl (as low alkyl group, for example, methyl), haloalkyl (as junior alkyl halides, CF for example
3, CHF
2C
2F
5Or CH
2F), alkoxyl group (as lower alkoxy, for example methoxyl group), halogenated alkoxy (as halogenated lower alkoxy, OCHF for example
2And OCF
3), nitro, amino, alkylthio (as the low alkyl group sulfo-, for example methyl sulfo-) ,-COOH ,-CONHSO
2R
5,-CONH
2,-CONHR
5-CONHOR
7(R wherein
7Be low alkyl group, as methyl) ,-COOH(R
4) COOR
3,-NHSO
2R
7,-N (SO
2R
7) ,-SCH(R
4) COR
3Or-NHCH(R
4) COR
3Or R
3[CO-CH(R
4)-O] n or NCCH(R
4) O-[CO-CH(R
4)-O] m, and M is CH or N.
Z, R
1, R
3, R
4, R
5And R
6(and Ar, R
a, R
b, X and Y) and (carry out) selecting Ar, R as previously described
aAnd R
b, making methoxyl group analogue or alkynes propoxy-analogue (wherein Q ' is methoxyl group or alkynes propoxy-, replaces above-mentioned Q ') is a kind of weedicide.
In compound preferably of the present invention, (carrying out) selects R
a, R
bWith Ar(or X and Y), make the methoxyl group analogue or the alkynes propoxy-analogue of this compound preferably have tangible herbicidal properties, to at least a following plants kind, when using at least a following manner and ratio and be 0.5 kg/ha, this analogue shows at least 50% kill ratio, and when application percentage is 0.1 kg/ha, show this 50% kill ratio better:
Kind: velvetleaf (Abutilon theophrasti), Herba Setariae Viridis (Setaria Viridis); Mode: before the bud, behind the bud.The available method what follows of the test of this weeding activity is carried out (under title " weeding activity ").
Exemplary compounds of the present invention (comprising some intermediate) is listed in table 1.
By common described step or method similar with it or identical and that in this field, know in the utilization document, can prepare compound of the present invention.In the following example 1, starting material is the hydroxy analogs (this hydroxy analogs can obtain by handling corresponding methoxyl group analogue, described in the embodiment 1E of the world (patent) of having announced application WO85/04307) of compound.Handle this hydroxy analogs to form nitrophenyl ether, handle it then to form hydroxy phenyl ether, the more suitable part of etherificate.Other method is as described below.In method B, a kind of compound of this process, wherein " M " is N, replaced C H describes; In that method, by using BBr
3Handle methoxypyridine base ether and prepare hydroxy-pyridyl ether.In method C, the first step is that etherificate is to introduce R
2Group reduces (on the Ar group) to form a kind of amino group by nitro substituent then, is converted into a kind of chlorine substituent then.Method D and E relate to manufacturing Q '-Ar-NH
2Compound, its NH
2Group can be converted into the Triazolinones part with a kind of method of routine then.In method D, NH
2Group by acidylate so that in each reaction process, protect it.In method E, by nitrated, NH is introduced in reduction then
2Group.When particularly use through selecting reagent with the product that forms embodiment 1 (or, in method B, when the corresponding pyridine compound) describing these methods, the those of skill in the art in this area will understand that similar reactant can be used for forming other compound disclosed herein.
Method B:1-(4-chloro-2-fluoro-5-hydroxy phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2,4-triazole-5(1H)-ketone earlier with sodium hydride [for example at N, dinethylformamide (" DMF ")] reaction, then with a kind of suitably substituted 5-methoxypyridine (for example 2-fluoro-or 2-chloro-5-methoxypyridine) to form 1-[4-chloro-2-fluoro-5-(5-methoxypyridine-2-yl) the oxo phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2, the 4-triazole-5(1H)-ketone.Handle (for example in methylene dichloride) with boron tribromide then, react to form corresponding 2-[5-[2-chloro-4-fluoro-5-(4-difluoromethyl-4 with a kind of 2 bromopropionic acid alkyl (for example ethyl) ester (for example in the presence of salt of wormwood and acetone) again, 5-dihydro-3-methyl-5-oxo-1H-1,2, the 4-triazol-1-yl) phenoxy group] pyridine-2-yl] the hydroxy-propionic acid alkyl ester.
Method C: at a kind of alkali (as at N, sodium hydride in the dinethylformamide) exists down, 1-(2,5-two fluoro-4-nitrophenyls)-and 4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2,4-triazole-5(1H)-ketone and a kind of 2-(4-hydroxyphenoxy) reaction of propionic acid alkyl (for example ethyl) ester is to form 2-[4-fluoro-2-nitro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2, the 4-triazol-1-yl) phenoxy group] phenoxy group] alkyl propionates.By redox nitryl group (for example in the ethanol of platinum oxide) with catalytic amount to form 2-[4-[2-amino-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2, the 4-triazol-1-yl) phenoxy group] phenoxy group] alkyl propionates.Handle then (as using Sodium Nitrite and hydrochloric acid, use cupric chloride (I) to form corresponding 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4 then, 5-dihydro-3-methyl-5-oxo-1H-1,2, the 4-triazol-1-yl) phenoxy group]-phenoxy group] alkyl propionates.
Method D:4-chloro-2-fluoro-5-hydroxyacetanilide and the reaction of 4-fluoronitrobenzene (for example at a kind of alkali, having heating down as sodium hydride and DMF) are to form 4-chloro-2-fluoro-5-(4-nitro-phenoxy) Acetanilide.Reductive NO
2Group (as by hydrogenation in the ethanol of the platinum oxide with catalytic amount) is to form the 5-(4-amino-benzene oxygen)-4-chloro-2-fluoro Acetanilide.Handle latter's (for example use Sodium Nitrite and sulfuric acid, use copper sulfate (II) then) to form 4-chloro-2-fluoro-5-(4-hydroxyphenoxy) Acetanilide.With alkylogen, react to form 4-chloro-2-fluoro-5-(4-methoxyl group phenoxy group then as methyl-iodide (for example in the presence of salt of wormwood and acetone)) Acetanilide.The hydrolysis latter (as using hydrochloric acid) to be to form corresponding aniline, for example 4-chloro-2-fluoro-5-(4-methoxyl group phenoxy group) aniline.
Method E:2,5-difluoro nitrobenzene and the reaction of 4-methoxyphenol (for example at a kind of alkali, existing down as sodium hydride and DMF) are to form 5-fluoro-2-(4-methoxyl group phenoxy group) oil of mirbane.Reduction nitryl group (as by hydrogenation in the ethanol of the platinum oxide with catalytic amount) is to form 5-fluoro-2-(4-methoxyl group phenoxy group) aniline.The nitrated latter (as using nitric acid and sulfuric acid) is to form 5-fluoro-2-(4-methoxyl group phenoxy group)-the 4-N-methyl-p-nitroaniline.Handle latter's (for example, using cupric chloride (I) then) to form 4-chloro-2-fluoro-5-(4-methoxyl group phenoxy group earlier with SODIUMNITRATE and hydrochloric acid) oil of mirbane.Reduction nitryl group (for example by hydrogenation in the ethanol of the platinum oxide with catalytic amount) is to form corresponding 4-chloro-2-fluoro-5-(4-methoxyl group phenoxy group) aniline.
Certainly, the substituting group that is present in the final product can import in each stage.For example in method D and E, methoxyl group can be converted into a kind of Q group in a follow-up phase of this process, for example a C
2H
5O-CO-CH(CH
3)-O-group, or latter's group can be imported into earlier, as by in method D, replace methyl-iodide with the 2 bromopropionic acid ethyl ester or by in method E, use the 2-(4-hydroxyphenoxy) ethyl propionate replacement 4-methoxyphenol.
Embodiment 1
2-[4-[(2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2, the 4-triazol-1-yl) phenoxy group] phenoxy group] the ethyl propionate steps A: phenyl 1-[4-chloro-2-fluoro-5-(4-nitro-phenoxy)]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2, the 4-triazole-5(1H)-ketone
To at 30 milliliters of N, drip lentamente at 30 milliliters of N in a kind of the stirring the mixture of the gram of 0.91 in the dinethylformamide (0.019 mole) sodium hydride, in the dinethylformamide 5.50 gram (0.019 mole) 1-[4-chloro-2-fluoro-5-hydroxy phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2, a kind of solution of 4-triazole-5(1H)-ketone.In this mixture, add 2.68 gram (0.019 mole) 4-fluoronitrobenzenes.At room temperature stirred this gained mixture about 18 hours, and heated 1 hour down at 80 ℃ then.Cool off this mixture, and it is poured in the frozen water.Extract this aqueous mixture with diethyl ether.The extraction liquid anhydrous magnesium sulfate drying, and filter.Vapourisation under reduced pressure filtrate, receive 6.0 gram 1-[4-chloro-2-fluoro-5-(4-nitro-phenoxies) phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2,4-triazole-5(1H)-ketone is a kind of solid, fusing point 115-117 ℃, the compound 4 in the table 1.
Nuclear magnetic resonance spectrum is consistent with the structure that is proposed.
Step B:1-[5-(4-amino-benzene oxygen)-4-chloro-2-fluorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2, the 4-triazole-5(1H)-ketone
In the presence of the platinum oxide that catalytic amount (0.30 gram) arranged, hydrogenation is dissolved in the gram of 5.80 in 100 milliliters of ethanol (0.015 mole) 1-[4-chloro-2-fluoro-5-(4-nitro-phenoxy) phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2, the 4-triazole-5(1H)-ketone, produce 4.6 gram 1-[5-(4-amino-benzene oxygens)-4-chloro-2-fluorophenyl]-4-difluoro-methoxy-4,5-dihydro-3-methyl isophthalic acid, 2, the 4-triazole-5(1H)-ketone, be a kind of solid, the compound 3 in the fusing point 133-135 ℃ table 1.
Nuclear magnetic resonance spectrum is consistent with the structure that is proposed
Step C:1-[4-chloro-2-fluoro-5-(4-hydroxyphenoxy) phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2, the 4-triazole-5(1H)-ketone
When keeping 20～25 ℃ of temperature, with 4.4 gram (0.011 mole) 1-[5-(4-amino-benzene oxygens)-4-chloro-2-fluorophenyl]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2,4-triazole-5(1H)-ketone is incorporated in the vitriol oil of 4.0 milliliters of stirrings.To wherein adding a kind of solution that is dissolved in the gram of 0.89 in 6.0 ml waters (0.13 mole) Sodium Nitrite, continue simultaneously to keep temperature to be about 20 ℃.After adding, stirred this mixture 30 minutes down at 20 ℃.By a Glass tubing this mixture is joined 32.0 gram (0.13 mole) copper sulfate (II) chloroazotic acid compounds, 80 ml waters and a kind of stirring of 30 milliliters of dimethylbenzene, the bottom of backflow mixture.After adding, this mixture 1 hour refluxes.Cool off this mixture, and make organic phase and aqueous phase separation.Extract this organic phase with a kind of aqueous sodium hydroxide solution (being dissolved in the gram of 6.0 in 250 ml waters sodium hydroxide ball).With concentrated hydrochloric acid this alkaline extraction liquid that neutralizes, form a kind of precipitation.By solid collected by filtration, receive 2.3 gram 1-[4-chloro-2-fluoro-5-(4-hydroxyphenoxies) phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2,4-triazole-5(1H)-ketone, fusing point 162-165 ℃, the compound 2 in the table 1.
Step D:2-[4-[(2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl) phenoxy group] phenoxy group] ethyl propionate
0.60 gram (0.0015 mole) 1-[4-chloro-2-fluoro-5-(4-hydroxyphenoxy that will be in 30 milliliters of acetone) phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, 2,4-triazole-5(1H)-ketone, 0.54(0.0030 mole) 2 bromopropionic acid ethyl ester and 0.32 gram (0.0023 mole) salt of wormwood reflux 6 days.Cool off this mixture, and filter.Vapourisation under reduced pressure filtrate stays a kind of resistates.This resistates is by the silicagel column chromatography purifying with the methylene dichloride wash-out, produce 0.43 gram 1-[4-[(2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2, the 4-triazol-1-yl) phenoxy group] phenoxy group] ethyl propionate, be a kind of solid, 128～129 ℃ of fusing points, the compound 5 in the table 1.
Nuclear magnetic resonance spectrum is consistent with the structure that is proposed.
Embodiment 2
N-methylsulfonyl-2-[4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl) phenoxy group] phenoxy group]
Propionic acid amide
With with embodiment 1 in the identical method of step D; make 0.60 gram (0.0015 mole) 1-[4-chloro-2-fluoro-5-(4-hydroxyphenoxy in 20 milliliters of acetone) phenyl]-4-difluoromethyl-4; 5-dihydro-3-methyl isophthalic acid; 2; the 4-triazole-5(1H)-ketone; 0.32 gram (0.0014 mole) N-methylsulfonyl-2-bromine propionic acid amide and 0.24 gram (0.0017 mole) salt of wormwood reaction; produce 0.3 gram N-methylsulfonyl 2-[4-[2-chloro-4-fluoro-5-(4-difluoromethyl-45-dihydro-3-methyl-5-oxo-1H-1; 2; the 4-triazol-1-yl) phenoxy group] phenoxy group] propionic acid amide; be a kind of oil, the compound 32 in the table 1.
Nuclear magnetic resonance spectrum is consistent with the structure that is proposed.
Other compound of the present invention can prepare by the method for knowing in the top method that exemplifies or this field.
Weeding activity
Comprise Gossypium (Gossypium hirsutumvar.Stoneville) in order to the plant test approaches that shows the weeding activity of demonstrate,proving compound of the present invention, soybean (Glycine max var.Williams), corn (Zea mays var.Agway 595s), wheat (Triticum aestivium var.Prodax), Oryza (Oryza sativa var.Labelle), Herba seu Flos Convolvuli arvensis (Convolvulus arvensis), (Ipomea lacunosa or Ipomea hederacea) leads a cow, velvetleaf (Abutilon theophrasti), barnyard grass (Echinochloa crus galli), Herba Setariae Viridis (Setaria viridis), stone thatch Chinese sorghum (Sorghum halepense) and charlock (Brassica raber).
With the seed of this plant test approaches or stem tuber be planted in be contained in the shallow seedbed of disposable cellulosic in the ditch furrow of the sandy loam of wet sterilization.The sand of equal portions and the topsoil of sandy loam (preparation) are placed each top, shallow seedbed, thick approximately 0.5 centimetre equably.
Water to the shallow seedbed that is used for the bud Pretesting, the solution with an amount of this test compounds in containing a small amount of (the as many as 0.5%v/v) acetone of Sorbitol Powder one lauric acid ester emulsifying agent/solubilizing agent and the mixture of water makes it to drench then.The concentration of change this test compounds in solution to provide an application percentage scope, is generally 8.0 kg/ha and Qi Yue amount.This shallow seedbed is placed greenhouse, and regularly watered 21 days, write down the phytotoxicity data during this period to this soil surface.
The shallow seedbed that will be used for testing behind the bud places greenhouse, and waters 8-10 days, sprays the solution of this test compounds in a kind of acetone-water that contain up to 0.5% Sorbitol Powder, one lauric acid ester then to the leaf of this test plants of having emerged.After spraying, this leaf was kept dry 24 hours, regularly watered then 21 days, and record phytotoxicity data.
Tabulate down 3 and table 4 in provided all cpds of the present invention by the application percentage of selecting under the data of weeding.These test compounds are used the numbering sign corresponding to table 1 therein.
In table 3 and table 4:
" kg/ha " is the kilogram number of per hectare, and
" %C " is the percentage inverse amplification factor.
In weeding is used, this compound by with herbicidally effective amount therewith in the field auxiliary and carrier commonly used mix, process preparation becomes the composition of weeding, using auxiliary and carrier is for required particular utility, promote the diffusion of active ingredient, this is owing to recognize that a kind of formulation of poisonous substance and application mode can be to the active influential facts of material in the given purposes.Therefore, the mode required according to application, but supply the granule of the compound process preparation one-tenth of agricultural existing weeding as larger particle size, water miscible or water dispersible granules agent, pulvis, wettable powder, missible oil, solution or any several other known formulation types.
Say that to being used for before the bud in the region of needs inhibition plant, the composition of these weedings is often with sprays, pulvis or granule form are employed.Bud rear defence to the plant-growth of field planting removes, and sprays or pulvis are the most frequently used.These formulations can contain few to 0.5% activeconstituents to as many as 95% or more multiple amount.
Pulvis is the broken solid of activeconstituents and fine powder (as talcum, natural clay, diatomite), powder (as walnut parting and cotton seed meal), and as the dispersion agent of poisonous substance and other organic and inorganic free-pouring mixture of carrier; The broken solid average particle size particle size of these fine powders is less than about 50 microns.A useful herein typical wp formula is compound and the 99.0 parts of talcums that contain 1.0 parts of weedings.
Wettable powder also is equally to the useful formulation of weeding before the bud and behind the bud, exists with the particulate form that easily is dispersed in the water or the fine powder in other dispersion agent is broken.This wettable powder is applied in the soil mainly as dry powder doses or the emulsion form in water or in other liquid.The carrier of typical wettable powder comprise Fuller's earth, kaolin, silica and other high-absorbable, easy moistening inorganic diluents.According to the absorptivity of carrier, generally prepare wettable powder and comprise about 5～80% activeconstituentss, and also comprise a spot of wetting agent, dispersion agent or emulsifying agent usually to promote dispersion.For example, a useful wettable powder agent prescription contains the compound of 80.8 parts of weedings, 17.9 parts of Pa Ermeituo clays (Palmetto clay), and 1.0 parts of sodium lignosulfonates and 0.3 part of alpha-sulfonated fatty adoption ester as wetting agent.Usually, will in for the bucket mix formulation that use before the bud, add and replenish wetting agent and/or oil, with promote its on leaf dispersion and by plant absorbing.
Other uses useful formulation to weeding is missible oil.Missible oil is formed for the uniform liquid or the pasty state that can be dispersed in the water or in other dispersion agent, and can be made up of herbicidal compound and a kind of liquid or solid emulsifying agent fully, or also can contain a kind of liquid vehicle.As dimethylbenzene, heavy aromatics petroleum naphtha, isophorone or other nonvolatile organic solvent.When using for weeding, these enriched materials are dispersed in the water or in other liquid carrier, and are applied to pending region as sprays usually.According to application method, the percent by weight of main activeconstituents can change.But generally comprise the activeconstituents of 0.5 to 95% weight of forming by weeding.
The typical wetting agent, dispersion agent or the emulsifying agent that use in agricultural formulation comprise: for example, the sulfonate of alkyl and alkylaryl and vitriol and their sodium salt, polyvalent alcohol, and the tensio-active agent of other type, many in them can buy on market.In use, tensio-active agent generally comprises the weeding composition of 1% to 15% weight.
Other is used useful formulation to weeding and comprises: (for example acetone, alkylated naphthalene, dimethylbenzene or other organic solvent) activeconstituents is pressed the consoluet simple solution of desired concn in a kind of solvent.Particle formulation, its toxicity are loaded on the thicker particle, particularly are beneficial to the infiltration of aerial application or nurse crop canopy.Also available pressurized spray agent is typically aerosol, and wherein activeconstituents is to be dispersed into the broken form of fine powder, and this is because the result of the evaporation of lower boiling dispersion agent solvent carrier (as fluorine Lyons).It also is useful formulation that water miscible or water dispersible granules agent is used the weeding of compound of the present invention.This particle formulation is free-pouring, dustless, and soluble in water or water is mixable.United States Patent (USP) 3,920, the soluble or easy dispersed particles formulation described in No. 442 is effective with herbicidal compound of the present invention wherein.
Active herbicidal compound of the present invention can be with sterilant, sterilant, nematocides, plant-growth regulator, fertilizer or other agricultural chemical process preparation and/or application, and on agricultural, both can be used as effective soil disinfectant, also can be used as weedicide selectively.When using compound of the present invention, no matter be independent process preparation or with other agricultural chemical hybrid process preparation, certainly all will be with the active compound of certain significant quantity and concentration; This amount can be low to moderate, 2 gram/hectares or lower for example, and for example about 1～250 gram/hectare is preferably about 4～30 gram/hectares.
Active herbicidal compound of the present invention can be used for and other combinations of herbicides, for example, they can mix with equivalent or relatively large known weedicide, for example chloroacetanilide weedicide such as 2-chloro-N-(2,6-diethyl phenyl)-and the N-(methoxymethyl) ethanamide (alachlor), 2-chloro-N-(2-ethyl-6-aminomethyl phenyl)-N-(2-methoxyl group-1-methylethyl) ethanamide [methoxy-DDT metolachlor)], and N-chloracetyl-N-(2,6-diethyl phenyl) glycine [diethyl phenyl ethyl (diethatyl-ethyl)]; The benzothiadiazine herbicides is as the 3-(1-methylethyl)-(1H)-2,1, the 3-benzothiadiazine-4-(3H)-ketone-2,2-dioxide (bentazon); Triazine herbicides is as 6-chloro-N-ethyl-N-(1-methylethyl)-1,3,5-triazines-2,4-diamines (G-30027), and 2-[4-chloro-6-(ethylamino)-1,3,5-triazines-2-yl] amino-2-methyl propionitrile (bladex; Dinitraniline (dinitrolaniline) weedicide, as 2,6-dinitrobenzene-N, N-dipropyl-4-(trifluoromethyl) aniline (trifluralin); And the aryl carbamide weedicide, as N '-(3, the 4-dichlorophenyl)-N, N-dimethyl urea (Diuron Tech) and N, N-dimethyl-N '-[the 3-(trifluoromethyl) phenyl] urea (fluometuron).
The formulation of obvious compound of the present invention and application can have various variations, and without prejudice to the inventive concept described in the claim of this paper.
Table 1
Compound
Numbering R
aR
bR
2R
1X Y
1 CHF
2CH
34-NO
23-CN F Cl
2 CHF
2CH
34-OH H F Cl
3 CHF
2CH
34-NH
2H F Cl
4 CHF
2CH
34-NO
2H F Cl
5 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F Cl
6 CHF
2CH
34-OCH
2C＝CH H F Cl
7 CHF
2CH
34-OCH（CH
3）CO
2CH
3H F Cl
8 CH
3CH
34-OCH（CH
3）CO
2CH
3H F Cl
9 CH（CH
3）
2CH
34-OCH（CH
3）CO
2CH
3H F Cl
10 C
2H
5CH
34-OCH（CH
3）CO
2CH
3H F Cl
11 CH
2CH
2CH
2F CH
34-OCH（CH
3）CO
2CH
3H F Cl
Table 1(is continuous)
Compound
Numbering R
aR
bR
2R
1X Y
12 CH
2CH
2F CH
34-OCH（CH
3）CO
2CH
3H F Cl
13 CH
2CH
2CH
3CH
34-OCH（CH
3）CO
2CH
3H F Cl
14 CH
2CH＝CH
2CH
34-OCH（CH
3）CO
2CH
3H F Cl
15 CH
2C＝CH CH
34-OCH（CH
3）CO
2CH
3H F Cl
16 CHF
2Cl 4-OCH（CH
3）CO
2CH
3H F Cl
17 CHF
2Br 4-OCH（CH
3）CO
2CH
3H F Cl
18 CHF
2F 4-OCH（CH
3）CO
2CH
3H F Cl
19 CHF
2CH（CH
3）
24-OCH（CH
3）CO
2CH
3H F Cl
20 CHF
2SCH
34-OCH（CH
3）CO
2CH
3H F Cl
21 CHF
2SO
2CH
34-OCH（CH
3）CO
2CH
3H F Cl
22 CHF
2SCF
34-OCH（CH
3）CO
2CH
3H F Cl
Table 1(is continuous)
Compound
Numbering R
aR
bR
2R
1X Y
23 CHF
2SO
2CF
34-OCH（CH
3）CO
2CH
3H F Cl
24 CHF
2C
2H
54-OCH（CH
3）CO
2CH
3H F Cl
25 CHF
2H 4-OCH（CH
3）CO
2CH
3H F Cl
26 CHF
2CH
34-OCH（CH
3）CO
2H H F Cl
27 CHF
2CH
34-OCH（CH
3）CONH
2H F Cl
28 CHF
2CH
34-OCH（CH
3）CONHCH
3H F Cl
29 CHF
2CH
34-OCH（CH
3）CON（CH
3）
2H F Cl
30 CHF
2CH
34-OCH（CH
3）CON（CH
3）OCH
3H F Cl
31 CHF
2CH
34-OCH（CH
3）CON（CH
2CH＝CH
2）
2H F Cl
32 CHF
2CH
34-OCH（CH
3）CONHSO
2CH
3H F Cl
33 CHF
2CH
34-OCH（CH
3）CON（CH
3）SO
2CH
3H F Cl
Table 1(is continuous)
Compound
Numbering R
aR
bR
2R
1X Y
34 CHF
2CH
34-OCH（CH
3）CON（C
2H
5）SO
2CH
3H F Cl
35 CHF
2CH
34-OCH（CH
3）CONHSO
2CH
3H F Cl
36 CHF
2CH
34-OCH（CH
3）CON（CH
3）SO
2CF
3H F Cl
37 CHF
2CH
34-OCH（CH
3）CONHSO
2C
2H
5H F Cl
38 CHF
2CH
34-OCH（CH
3）CONHSO
2C
3H
7H F Cl
39 CHF
2CH
34-OCH（CH
3）CONHSO
2C
6H
5H F Cl
40 CHF
2CH
34-OCH（CH
3）CONHSO
2（4-ClC
6H
4） H F Cl
41 CHF
2CH
34-OCH（CH
3）CONHSO
2（4-CH
3OC
6H
4） H F Cl
42 CHF
2CH
34-OCH
2CONHSO
2CH
3H F Cl
43 CHF
2CH
34-OCH
2CO
2H H F Cl
44 CHF
2CH
34-OCH
2CO
2C
2H
5H F Cl
Table 1(is continuous)
Compound
Numbering R
aR
bR
2R
1X Y
45 CHF
2CH
34-OCH
2C＝N H F Cl
46 CHF
2CH
34-OCH（CH
3）CN H F Cl
47 CHF
2CH
34-OCH（CH
3）CO
2CH（CH
3）C＝CH H F Cl
48 CHF
2CH
34-OCH
2COCH
3H F Cl
49 CHF
2CH
33-OCH（CH
3）CO
2C
2H
5H F Cl
50 CHF
2CH
33-OCH（CH
3）CO
2H H F Cl
51 CHF
2CH
33-OCH（CH
3）CONH
2H F Cl
52 CHF
2CF
33-OCH（CH
3）COHSO
2CH
3H F Cl
53 CHF
2CH
33-OCH（CH
3）CONHSO
2C
6H
5H F Cl
54 CHF
2CH
34-OCH（CH
3）CO
2C
2H
52-Cl F Cl
55 CHF
2CH
34-OCH（CH
3）CO
2C
2H
52-F F Cl
Table 1(is continuous)
Compound
Numbering R
aR
bR
2R
1X Y
56 CHF
2CH
34-OCH（CH
3）CO
2C
2H
53-Cl F Cl
57 CHF
2CH
34-OCH（CH
3）CO
2C
2H
53-F F Cl
58 CHF
2CH
34-OCH（CH
3）CO
2C
2H
52-CH
3F Cl
59 CHF
2CH
34-OCH（CH
3）CO
2C
2H
53-CH
3F Cl
60 CHF
2CH
34-OCH（CH
3）CO
2C
2H
52-OCH
3F Cl
61 CHF
2CH
34-OCH（CH
3）CO
2C
2H
53-OCH
3F Cl
62 CHF
2CH
34-OCH（CH
3）CO
2C
2H
52-NO
2F Cl
63 CHF
2CH
34-OCH（CH
3）CO
2C
2H
53-NO
2F Cl
64 CHF
2CH
34-OCH（CH
3）CO
2C
2H
52，6-F
2F Cl
65 CHF
2CH
34-OCH（CH
3）CO
2C
2H
52，3-F
2F Cl
66 CHF
2CH
33-OCH（CH
3）CO
2C
2H
54-NO
2F Cl
Table 1(is continuous)
Compound
Numbering R
aR
bR
2R
1X Y
67 CHF
2CH
33-OCH（CH
3）CO
2C
2H
54-Cl F Cl
68 CHF
2CH
33-OCH（CH
3）CO
2C
2H
54-Br F Cl
69 CHF
2CH
33-OCH（CH
3）CO
2C
2H
54-F F Cl
70 CHF
2CH
33-OCH（CH
3）CO
2C
2H
56-F F Cl
71 CHF
2CH
33-OCH（CH
3）CO
2C
2H
54-CN F Cl
72 CHF
2CH
33-OCH（CH
3）CO
2C
2H
54-OCH
3F Cl
73 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H H H
74 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F Br
75 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F CH
3
76 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F NO
2
77 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F OCH
Table 1(is continuous)
Compound
Numbering R
aR
bR
2R
1X Y
78 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F CF
3
79 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F F
80 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F SCH
3
81 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H H Cl
82 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H Cl Cl
83 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H Br Cl
84 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H CH
3Cl
85 CHF
2CH
34-OCH（CH
3）CO
2C
2H
5H F H
86 CHF
2CH
33-OCH（CH
3）CO
2C
2H
52，4-Cl
2H H
87 CHF
2CH
33-OCH（CH
3）CO
2C
2H
52F，4Cl H H
Table 1(is continuous)
Compound
Numbering R
aR
bR
2R
1X Y
88 CHF
2CH
34-OCH（CH
3）CO
2Na H F Cl
89 CHF
2CH
34-OCH（CH
3）CO
2K H F Cl
90 CHF
2CH
34-OCH（CH
3）CO
2N
+（C
2H
5）
4H F Cl
91 CHF
2CH
34-OCH（CH
3）CO
2CH（CH
3）
2H F Cl
92 CHF
2CH
34-NO
2H Cl Cl
Other exemplary compounds compound 1-92 with the front respectively is the same, just has R
2Substituent aromatic nucleus is that structural formula is
A kind of pyridine ring, with respect to the free valency among the compound 1-92 as described (being connected to 0), have R
2And R
1On same position; Referring to the compound that for example produces by top method B.
Table 2
Qualitation
The compound ultimate analysis
The numbering fusing point (℃) empirical formula C H N
1 164-165.5 C
17H
9ClF
3N
5O
4C 46.43 2.06 15.93
F 46.60 2.28 15.84
2 162-165 C
16H
11ClF
3N
3O
3
3 133-135 C
16H
12ClF
3N
4O
2
4 115-117 C
16H
10ClF
3N
4O
4
5 128-129 C
21H
19ClF
3N
3O
5C 51.91 3.94 8.65
F 51.81 3.69 8.79
6 86-88 C
19H
13ClF
3N
3O
3C 53.84 3.09 9.91
F 53.43 3.07 9.80
7 136-138 C
20H
17ClF
3N
3O
5C 50.89 3.64 8.91
F 50.58 3.53 8.78
32 oily C
20H
18ClF
3N
4O
6S
91 113.5-115 C
22H
21ClF
3N
3O
5
92 viscous crude C
16H
10Cl
2F
2N
4O
4
Table 3
Weeding activity before the bud
Compound number 1234
Ratio (kg/ha) 8.0 4.0 4.0 4.0
%C %C %C %C
Kind
Cotton 10 70 10 0
Soybean 10 100 80 10
Corn 50 85 60 20
Rice 0 95 60 20
Wheat 20 100 60 10
Lead a cow 20 90 70 10
Charlock-100 100 70
Velvetleaf 80 100 100 80
Barnyard grass 90 100 95 30
Herba Setariae Viridis 50 100 100 70
Stone thatch Chinese sorghum 0 85 100 70
Compound number 567
Ratio (kg/ha) 4.0 0.5 0.5
%C %C %C
Kind
Cotton 70 10 50
Soybean 70 30 90
Corn 60 10 95
Rice 70 10 80
Wheat 80 10 95
Lead a cow 100 40 100
Charlock 100 40 100
Velvetleaf 100 80 100
Barnyard grass 100 95 95
Herba Setariae Viridis 100 100 100
Stone thatch Chinese sorghum 100 40 95
Table 4
Weeding activity behind the bud
Compound number 1234
Ratio (kg/ha) 8.0 4.0 4.0 4.0
%C %C %C %C
Kind
Cotton 60 100 95 70
Soybean 60 95 70 50
Corn 50 95 100 60
Rice 30 95 70 20
Wheat 20 100 95 20
Lead a cow 60 100 100 90
Charlock-70 95 70
Velvetleaf 100 100 100 100
Barnyard grass 40 100 95 30
Herba Setariae Viridis 80 95 100 30
Stone thatch Chinese sorghum 30 95 85 30
Compound number 567
Ratio (kg/ha) 4.0 0.5 0.5
%C %C %C
Kind
Cotton 100 95 100
Soybean 100 80 100
Corn 100 100 105
Rice 95 60 100
Wheat 100 95 100
Lead a cow 100 100 100
Charlock 100 95 100
Velvetleaf 100 100 100
Barnyard grass 100 90 100
Herba Setariae Viridis 100 95 100
Stone thatch Chinese sorghum 100 95 100
Claims (15)
1, a kind of compound is characterized in that structural formula is
Wherein Q ' is:
R wherein
2Be H, halogen, alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, nitro, amino, alkylthio ,-COOH ,-CONHSO
2R
5,-CONH
2,
-CONHR
5,-CONHOR
7(R wherein
7Be low alkyl group, for example methyl) ,-COOCH (R
4) COOR
3,-NHSO
2R
7,-N (SO
2R
7)
2,-SCH (R
4) COR
3,-NHCH (R
4) COR
3, R
3[CO-CH (R
4)-O]
nOr NCCH (R
4) O-[CO-CH (R
4)-O] m,
M is CH or N,
Z is O, S, and NH or alkylamino,
R
4Be H or CH
3,
R
3Be OH, alkoxyl group, alkenyloxy, alkynyloxy group, amino, virtue is amino, alkylamino, alkenyl amino, alkoxy amino, the halogenated alkyl alkyl-or structural formula be NHSO
2R
5Or-N (SO
2R
5) SO
2R
6, R wherein
5And R
6Be alkyl independently, the arlysulfonylamino of haloalkyl or aryl,
" n " is 1 or 2,
" m " is 0 or 1,
R
1Be H, alkyl, halogen, haloalkyl, nitro, alkoxyl group, alkylthio or cyano group,
Ar is a kind of phenyl ring that replaces with Ar, and (carrying out) selects R
aAnd R
bMake when Q ' be methoxyl group or alkynes propoxy-, replacement has Q ' time of the structural formula that provides above, compound is a kind of weedicide.
2, a kind of compound according to claim 1 is characterized in that wherein R
2Be R
3[CO-CH(R
4)-O] n or NCCH(R
4) O-[CO-CH(R
4)-O] m.
3, a kind of compound according to claim 2 it is characterized in that wherein n is 1, and m is 0.
4, a kind of compound according to claim 3 is characterized in that wherein M is CH.
5, a kind of compound according to claim 1 is characterized in that wherein R
2Be R
3[CO-CH(R
4)-O] n.
6, a kind of compound according to claim 5 is characterized in that wherein M is CH.
7, a kind of compound according to claim 6 is characterized in that Ar wherein is for having Q ' and having a kind of phenyl ring of halogen in its No. 2 positions and No. 4 positions, R in its No. 5 positions
bBe methyl and R
aBe difluoromethyl.
8, a kind of compound according to claim 7 is characterized in that wherein Ar has chlorine, fluorine or bromine in its No. 2 positions, and has chlorine or fluorine in its No. 4 positions.
9, a kind of compound according to claim 8 is characterized in that wherein Ar has F in its No. 2 positions.
10, a kind of weeding is formed, and it is characterized in that a kind of compound and a kind of suitable carrier of claim 1 of herbicidally effective amount mixes.
11, a kind of method of controlling undesirable plant-growth is characterized in that the composition in the claim 10 of the place of needs control application herbicidally effective amount.
12, a kind of weeding is formed, it is characterized in that a kind of herbicidally effective amount claim 5 compound and a kind of suitable carrier mix.
13, a kind of method of controlling undesirable plant-growth is characterized in that the composition in the claim 12 of the place of needs control application herbicidally effective amount.
14, a kind of weeding is formed, and it is characterized in that a kind of compound and a kind of suitable carrier of claim 9 of herbicidally effective amount mixes.
15, a kind of method of controlling undesirable plant-growth is characterized in that the composition in the claim 14 of the place of needs control application herbicidally effective amount.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89845386A | 1986-08-20 | 1986-08-20 | |
| US898,453 | 1986-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1032005A true CN1032005A (en) | 1989-03-29 |
Family
ID=25409480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN87105742A Pending CN1032005A (en) | 1986-08-20 | 1987-08-20 | Weedicide |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0322413A4 (en) |
| JP (1) | JPH02500271A (en) |
| KR (1) | KR880701527A (en) |
| CN (1) | CN1032005A (en) |
| BR (1) | BR8707779A (en) |
| HU (1) | HUT48799A (en) |
| WO (1) | WO1988001133A1 (en) |
| ZA (1) | ZA876179B (en) |
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|---|---|---|---|---|
| CN110072853A (en) * | 2016-12-16 | 2019-07-30 | 巴斯夫欧洲公司 | The benz triazolinone of weeding |
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| US5262390A (en) * | 1992-08-26 | 1993-11-16 | Fmc Corporation | Herbicical 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates |
| ID24479A (en) | 1997-03-14 | 2000-07-20 | Isk Americas Inc | DIARIL ETERS AND THE PROCESS OF MAKING HERBICIDE COMPOSITIONS AND DRYER CONTAINING ETER DIARIL |
| DE19901846A1 (en) * | 1999-01-19 | 2000-07-20 | Bayer Ag | New aryl-substituted aza-heterocyclic compounds, useful as pre- or post-emergence, total or selective herbicides, show defoliant, dessicant and especially weed-killing activity |
| EP2590951B1 (en) | 2010-07-09 | 2015-01-07 | Pfizer Limited | Benzenesulfonamides useful as sodium channel inhibitors |
| WO2012007883A1 (en) | 2010-07-12 | 2012-01-19 | Pfizer Limited | Sulfonamide derivatives as nav1.7 inhibitors for the treatment of pain |
| US8772343B2 (en) | 2010-07-12 | 2014-07-08 | Pfizer Limited | Chemical compounds |
| ES2525581T3 (en) | 2010-07-12 | 2014-12-26 | Pfizer Limited | N-sulfonylbenzamide derivatives useful as voltage-dependent sodium channel inhibitors |
| JP2013532185A (en) | 2010-07-12 | 2013-08-15 | ファイザー・リミテッド | Compound |
| US9102621B2 (en) | 2010-07-12 | 2015-08-11 | Pfizer Limited | Acyl sulfonamide compounds |
| AU2018373436C1 (en) | 2017-11-23 | 2023-10-19 | Basf Se | Herbicidal pyridylethers |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2846038A1 (en) * | 1978-10-23 | 1980-05-08 | Basf Ag | 1,2,4-TRIAZOLE DERIVATIVES, THEIR PRODUCTION AND USE |
| US4318731A (en) * | 1979-08-25 | 1982-03-09 | Nihon Nohyaku Co., Ltd. | Δ2 -1,2,4-triazolin-5-one derivatives and herbicidal usage thereof |
| US4404019A (en) * | 1980-12-24 | 1983-09-13 | Sumitomo Chemical Company, Limited | 3-Chloro-1-phenyl-1,2,4-triazolin-5-ones and their use as herbicides |
| CH651029A5 (en) * | 1980-12-25 | 1985-08-30 | Nihon Nohyaku Co Ltd | TRIAZOLINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND HERBICIDES CONTAINING IT. |
| US4636514A (en) * | 1982-08-13 | 1987-01-13 | The Dow Chemical Company | Aryl(aryloxy or arylthio)azolomethanes |
| DK348883A (en) * | 1982-08-13 | 1984-02-14 | Dow Chemical Co | ARYL (ARYLOXY OR ARYLTHIO) AZOLOMETHANES, THEIR PREPARATION AND USE |
| PH18938A (en) * | 1982-09-28 | 1985-11-11 | Sumitomo Chemical Co | 2-substituted phenyl-4,5,6,7-tetrahydro-2h-indazoles and their use |
| JPS59148785A (en) * | 1983-02-15 | 1984-08-25 | Sumitomo Chem Co Ltd | Pyridotriazolium derivative, its preparation and herbicide containing the same as an active ingredient |
| EP0177553A4 (en) * | 1984-03-29 | 1986-08-21 | Fmc Corp | Herbicidal 1-aryl-delta 2-1,2,4-triazolin-5-ones. |
| JPS62265275A (en) * | 1986-05-13 | 1987-11-18 | Nippon Nohyaku Co Ltd | Production of 1,2,4-triazolin-5-one derivative |
| JPS6330475A (en) * | 1986-07-25 | 1988-02-09 | Nippon Nohyaku Co Ltd | 1,2,4-triazolin-5-one derivative and use thereof |
-
1987
- 1987-08-05 BR BR8707779A patent/BR8707779A/en unknown
- 1987-08-05 WO PCT/US1987/001928 patent/WO1988001133A1/en not_active Application Discontinuation
- 1987-08-05 JP JP62505029A patent/JPH02500271A/en active Pending
- 1987-08-05 EP EP19870905518 patent/EP0322413A4/en not_active Withdrawn
- 1987-08-05 HU HU874354A patent/HUT48799A/en unknown
- 1987-08-20 CN CN87105742A patent/CN1032005A/en active Pending
- 1987-08-20 ZA ZA876179A patent/ZA876179B/en unknown
-
1988
- 1988-04-19 KR KR1019880700414A patent/KR880701527A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110072853A (en) * | 2016-12-16 | 2019-07-30 | 巴斯夫欧洲公司 | The benz triazolinone of weeding |
| CN110072853B (en) * | 2016-12-16 | 2023-07-25 | 巴斯夫欧洲公司 | Herbicidal phenyltriazolinones |
Also Published As
| Publication number | Publication date |
|---|---|
| HUT48799A (en) | 1989-07-28 |
| ZA876179B (en) | 1988-02-23 |
| EP0322413A4 (en) | 1989-10-04 |
| EP0322413A1 (en) | 1989-07-05 |
| WO1988001133A1 (en) | 1988-02-25 |
| KR880701527A (en) | 1988-11-03 |
| BR8707779A (en) | 1989-08-15 |
| JPH02500271A (en) | 1990-02-01 |
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