+

WO1992010484A1 - Herbicides - Google Patents

Herbicides Download PDF

Info

Publication number
WO1992010484A1
WO1992010484A1 PCT/GB1991/002167 GB9102167W WO9210484A1 WO 1992010484 A1 WO1992010484 A1 WO 1992010484A1 GB 9102167 W GB9102167 W GB 9102167W WO 9210484 A1 WO9210484 A1 WO 9210484A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
group
acetic acid
substituted
acid derivatives
Prior art date
Application number
PCT/GB1991/002167
Other languages
English (en)
Inventor
Christoph Harde
Gabriele KRÜGER
Gerhard Tarara
Nikolaus Heinrich
Klaus-Peter Gerbling
Richard Rees
Gerhard Johann
Graham Peter Jones
Original Assignee
Schering Agrochemicals Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Schering Agrochemicals Limited filed Critical Schering Agrochemicals Limited
Publication of WO1992010484A1 publication Critical patent/WO1992010484A1/fr

Links

Classifications

    • 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
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms

Definitions

  • This invention concerns new pyrimidinyloxy, pyrimidinylthio, triazinyloxy and triazinylthio acetic acid derivatives having herbicidal activity, processes for their preparation and compositions containing them.
  • the invention provides the acetic acid derivatives of the formula:
  • R is a group -COjR 1 , -CH 2 0H, -C0NHS0 2 R* or - C0NHS0 2 NR"R b , where R 1 is hydrogen or a salt- or ester- forming group, R* is alkyl or aryl, and R b is hydrogen. alkyl or aryl;
  • R 2 and R 3 which may be the same or different, are each halogen, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino;
  • A is a substituted or unsubstituted aryl, heterocyclyl or benzoheterocyclyl group, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl group;
  • X is oxygen or sulfur
  • Z is oxygen or sulfur; and salts thereof.
  • R 1 is an ester-forming group, it may for example be a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl group. It is preferably an unsubstituted group, especially an unsubstituted alkyl group.
  • R* and R b are each preferably methyl, ethyl, n- propyl, isopropyl or phenyl.
  • R 2 or R 3 is halogen, it is preferably chlorine.
  • R 2 and R 3 are each preferably alkyl or alkoxy, and both are preferably the same.
  • the group A is preferably a substituted or unsubstituted phenyl, pyridyl, naphthyl, furyl, thienyl, pyrrolyl, benzofuranyl , benzothiophenyl, indolyl, oxazolyl, thiazolyl or imidazolyl group, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl group.
  • A is a substituted phenyl, heterocyclyl or benzoheterocyclyl group
  • the substituent groups thereon are each preferably alkyl, alkoxy, amino, dialkylamino, nitro, halogen, trifluoromethyl or phenyl.
  • Any alkyl group in the compounds of the invention is preferably of 1 to 10, especially 1 to 4, carbon atoms, for example methyl, ethyl, n-propyl, isopropyl or t- butyl.
  • Any alkenyl or alkynyl group in the compounds of the invention is preferably of 2 to 10, especially 2 to 4 carbon atoms, for example vinyl, allyl or propargyl.
  • Any cycloalkyl group in the compounds of the invention is preferably of 3 to 8 carbon atoms, for example cyclopentyl or cyclohexyl.
  • Any cycloalkenyl group in the compounds of the invention is preferably of 4 to 8 carbon atoms, for example cyclopentenyl or cyclohexenyl.
  • alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl group present When any alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl group present is substituted, it may, for example, be substituted by one or more alkoxy, alkylthio, amino, alkylamino, dialkylamino, nitro, halogen or phenyl groups. Any cycloalkyl or cycloalkenyl group present may additionally be substituted by one or more alkyl groups.
  • R 1 is preferably hydrogen, methyl or ethyl.
  • R 2 and R 3 are preferably each methoxy or each methyl.
  • A is preferably alkyl of 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, or phenyl substituted by a methyl group or by one or two chlorine atoms.
  • X is preferably sulfur.
  • Z is preferably sulfur.
  • Specific preferred compounds of formula I are those of the Examples provided hereinafter. Particular mention may be made, however, of methyl 2-(4,6-dimethoxy- pyrimidin-2-ylthio)-2-(phenylthio)acetate.
  • the compounds of formula I where R is other than CH 2 OH may be prepared by a process in which a substituted pyrimidine or triazine of the formula: Q
  • XH where X is as defined hereinbefore, and the other being a leaving group, to give the desired compound.
  • the leaving group may be any convenient such group, for example a halogen atom, an alkylsulfinyl group, a phenylsulfinyl group, and alkylsulfonyl group or a phenylsulfonyl group.
  • the reaction is conveniently effected in a suitable solvent medium, eg an aromatic hydrocarbon, eg benzene, toluene, xylene, halogenated hydrocarbon solvents such as methylene chloride or chloroform, alcohols such as methanol, ethanol or isopropanol, ethers such as diethyl ether, di-isopropyl ether, tetrahydrofuran or 1,4- dioxane, ketones such as acetone or methyl ethyl ketone, esters such as methyl acetate or ethyl acetate, polar aprotic solvents such as dimethylformamide, dimethyl acetamide or dimethylsulfoxide, or nitriles, eg acetonitrile, or in water.
  • a suitable solvent medium eg an aromatic hydrocarbon, eg benzene, toluene, xylene, halogenated hydrocarbon solvents such as methylene
  • the base employed may be any convenient base, for example an alkali-metal or alkaline earth metal hydride.
  • hydroxide or carbonate eg sodium hydride, potassium hydride, calcium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate.
  • the reaction temperature employed may be from 0°C to the boiling point of the reaction mixture, eg from 0 to 100°C.
  • the compounds of formula I in which R represents a group CH 2 OH may be prepared by reduction of the corresponding compounds of formula I in which R represents -COOR 1 .
  • the reduction may be achieved for example by means of borane-dimethyl sulfide complex under conventional conditions for the use thereof.
  • the compounds of formula I may also be prepared by a method in which a compound of the formula:
  • the reaction is conveniently effected in a suitable solvent medium, eg an aprotic solvent such as benzene, toluene, xylene, tetrahydrofuran, diethyl ether, hexane, dimethylformamide or dimethyl sufoxide, and at a temperature of from -78°C to the boiling point of the reaction mixture, eg 0°C to 100°C.
  • a suitable solvent medium eg an aprotic solvent such as benzene, toluene, xylene, tetrahydrofuran, diethyl ether, hexane, dimethylformamide or dimethyl sufoxide
  • a suitable solvent medium eg an aprotic solvent such as benzene, toluene, xylene, tetrahydrofuran, diethyl ether, hexane, dimethylformamide or dimethyl sufoxide
  • the base employed may be any convenient base, for example sodium
  • the compounds of formula IV may themselves be prepared by a process in which a compound of the formula:
  • R, R 2 , R 3 , X and Y are as defined hereinbefore, is reacted in a suitable solvent with a halogenating agent to give the desired compound.
  • Suitable halogenating agents include in particular the N-halosuccinimides, especially N-bromosuccinimide.
  • the compounds of formula I may be interconverted into further compounds of formula I by • methods known per se.
  • alkali-metal, alkaline earth metal, ammonium and substituted ammonium salts of the compounds may be prepared by reaction of the compounds, particularly those where R represents -COOH, with a suitable alkali-metal, alkaline earth metal, or ammonium-containing base in a suitable polar solvent medium, and such salts may if desired be hydrolysed by the action of an appropriate acid to give the corresponding compounds in which R represents -COOH.
  • the compounds of formula I are herbicidally-active against a wide range of broad-leaved and grassy weeds. but are comparatively safe to certain crop species. They may thus be of use as herbicides, and especially as selective herbicides, particularly in the control of a range of weeds in cereals or other crops, eg wheat, rice, barley, maize, soya beans, oilseed rape, cotton or sugar beet.
  • One very important weed combated particularly well by the compounds of the present invention is cleavers ⁇ Galium aparine..
  • this invention provides a herbicidal composition which comprises one or more compounds of formula I in association with a suitable carrier and/or surface active agent.
  • compositions of the invention usually contain from 0.01 to 99% by weight of the present compounds, and are normally produced initially as concentrates containing from 0.5 to 99%, preferably from 0.5 to 85%, and especially from 10 to 50% by weight thereof. Such concentrates are diluted if necessary before application to the locus to be treated such that the active ingredient comprises from 0.01 to 5% by weight of the formulation applied.
  • the carrier may be water, in which case an organic solvent may also be present, though this is not usually employed.
  • a flowable suspension concentrate may be formed by grinding the compound with water, a wetting agent and a suspending agent,eg xanthan gum.
  • the carrier may alternatively be a water immiscible organic solvent, eg a hydrocarbon which boils within the range 130-270C, eg xylene, in which the compound is dissolved or suspended.
  • An emulsifiable concentrate containing a water immiscible solvent may be formed with a surface active agent so that the concentrate acts as a self-emulsifiable oil on admixture with water.
  • the carrier may alternatively be a water-miscible organic solvent eg 2-methoxy ethanol, methanol, propylene glycol, diethylene glycol, diethylene glycol monoethyl ether, methylformamide or dimethylformamide.
  • a water-miscible organic solvent eg 2-methoxy ethanol, methanol, propylene glycol, diethylene glycol, diethylene glycol monoethyl ether, methylformamide or dimethylformamide.
  • the carrier may alternatively be a solid, which may be finely divided or granular.
  • suitable solids are limestone, clays, sand, mica, chalk, attapulgite, diatomite, perlite, sepiolite, silicas, silicates, lignosulfonates and solid fertilizers.
  • the carrier can be of natural or synthetic origin or can be modified natural material. Wettable powders soluble or dispersible in water may be formed by admixing the compound in particulate form with a particulate carrier or spraying molten compound on to the particulate carrier, admixing a wetting agent and a dispersing agent and finely grinding the mixture.
  • An aerosol composition may be formed by admixing the compound with a propellant, eg a polyhalogenated alkane such as dichlorofluoromethane, and suitably also with a solvent.
  • 'surface active agent' is used in the broad sense to include materials variously called emulsifying agents, dispersing agents and wetting agents. Such agents are well known in the art.
  • the surface active agents used may comprise anionic surface active agents, for example mono- or di-esters of phosphoric acid with a fatty alcohol ethoxylate, or salts of such esters, fatty alcohol sulfates such as sodium dodecyl sulfate, ethoxylated fatty alcohol sulfates, ethoxylated alkylphenol sulfates, lignin sulfates, petroleum sulfonates, alkylaryl sulfonates such as alkyl-benzene sulfonates or lower alkylnaphthalene sulfonates, salts of sulfonated naphthaleneformaldehyde condensates, salts of sulfonated phenolformaldehyde condensates, or more complex sulfonates such as the amide sulfonates, eg the sulfonated condensation product of oleic acid and N-methyl taurine or
  • the surface active agents may also comprise non-ionic agents, for example condensation products or fatty acid esters, fatty alcohols, fatty acid amides or alkyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers eg sorbitan fatty acid esters, condensation products of such esters with ethylene oxide eg polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5- dec ⁇ n-4,7-diol, or ethoxylated acetylenic glycols.
  • non-ionic agents for example condensation products or fatty acid esters, fatty alcohols, fatty acid amides or alkyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers eg sorbitan fatty acid esters, condensation products of such esters with ethylene oxide
  • the surface active agents may also comprise cationic agents, for example alkyl- and/or aryl-substituted quaternary ammonium compounds such as cetyl trimethylammonium bromide, or ethoxylated tertiary fatty amines.
  • cationic agents for example alkyl- and/or aryl-substituted quaternary ammonium compounds such as cetyl trimethylammonium bromide, or ethoxylated tertiary fatty amines.
  • Preferred surface active agents include ethoxylated fatty alcohol sulfates, lignin sulfonates, alkyl-aryl sulfonates,salts of sulfonated naphthaleneformaldehyde condensates, salts of sulfonated phenolformaldehyde condensates, sodium oleoyl N-methyltauride, dialkyl sulfosuccinates, alkyl phenol ethoxylates, and fatty alkyl ethoxylates.
  • the present active compounds may be admixed with another pesticide, eg a herbicide, fungicide or insecticide, or a plant growth regulator, particularly another herbicide.
  • Suitable further herbicides include trietazine, linuron, CPA, dichlorprop, isoxaben, diflufenican, metolachlor, fluometuron, oxyfluorfen, fomesafen, bentazone, prometryne, norflurazon, chlomazone, EPTC, imazaquin, and especially isoproturon, methabenzthiazuron, trifluralin, ioxynil, bromoxynil, benazolin, mecoprop, fluroxypyr, alachlor, acifluorfen, lactofen, metribuzin, pendimethalin, ethofumesate, benfuresate, phenmedipham, benzophenap, butachlor, chlomethox fen, dimepiperate, mefenacet, molinate, naproanilide, oxadiazon, piperophos, pro etryne, pyraz
  • the invention provides a method of combating weeds at a locus infested or liable to be infested therewith which comprises applying to said locus an effective amount of one or more compounds of formula I.
  • the present compound may be applied to plants, the soil, land or aquatic areas, and particularly to a locus at which a crop is growing.
  • the compounds are active pre-emergence but particularly post-emergence, and especially at rates of application of from 0.005 to 1 kg/ha, more particularly from 0.01 to 0.5 kg/ha, especially 0.03 to 0.2 kg/ha.
  • Methyl (phenylthio)acetate (5g) , N-bromosuccinimide (5.8g) and benzoyl peroxide (O.lg) were suspended in carbon tetrachloride (150ml) , and the mixture was refluxed for 45 minutes. It was then cooled to 5°C and filtered, and the yellow solution was concentrated in a rotary evaporator. The oil obtained (7.1g) was dissolved in dimethylformamide (50ml) and was dripped into a suspension of 2-mercapto- ,6-dimethoxypyrimidine (4.68g) and potassium carbonate (1.87g) in dimethylformamide (50ml) .
  • Example 3 Example 3
  • Ethyl 2-ethoxy-2-hydroxyacetate (6.4g) was dissolved in dimethylformamide (50ml) and potassium carbonate (2.5g) was added. After stirring for 20 minutes, 4,6- dimethoxy-2-methylsulfonylpyrimidine (8.0g) was added, and the mixture was heated for 12 hours at 90°C. It was then poured into ice/water (100ml) and was extracted three times with ethyl acetate. The ester phases were washed with water, dried over sodium sulfate and evaporated.
  • Methyl phenoxyacetate (log) , N-bromosuccinimide (12.8g) and benzoyl peroxide (O.lg) were suspended in carbon tetrachloride (300ml) and the mixture was refluxed for 45 minutes. It was then cooled to 5°C and filtered, and the yellow solution was concentrated in a rotary evaporator. The oil obtained (14.7g) was dissolved in dimethylformamide (100ml) , and was dripped into a suspension of 2-mercapto-4,6-dimethoxypyrimidine (10.3g) and potassium carbonate (4.1g) in dimethylformamide (150ml) .
  • N-bromosuccinimide (17.8g) was added to a stirred solution of the product of stage (a) in carbon tetrachloride (250ml) , and the resulting suspension was gently refluxed over a 500W lamp for 3% hours. The solid was filtered off, and the filtrate was stripped to give a yellow liquid which was purified by flash chromatography (5% diethyl ether in hexane) to give 28.5g of the desired product.
  • stage (b) (1.7g) in dimethylformamide (5ml) was added to a stirred solution/suspension of ethanethiol (0.31g) and potassium carbonate (0.76g) in dimethylformamide (15ml) , and the resulting suspension was stirred at room temperature for 2 hours.
  • the mixture was poured into water (80ml) , and was extracted with ether (2 x 80ml) .
  • the combined extracts were washed with saturated sodium chloride solution, dried and stripped to give a colourless oil, which was purified by flash chromatography (5% diethyl ether in hexane) to give 0.41g of the desired product, identical to that of Example 12.
  • Example 27
  • Seeds of the test species listed below were each sown in 8.5cm square pots filled to within 2cm of the top with sterile loam, and were covered with a 2-5mm layer of loam.
  • the pots were watered, and then treated with the compounds of the Examples listed below formulated as a solution/suspension in 3:1 by volume of acetone and the wetting agent polyoxyethylene (20 mols) monolaurate solution (10 g per litre) by application to the soil surface in a spray cabinet.
  • the concentration of each test compound and volume of application were calculated to give the desired rate of application of the compound in 200 litres per hectare.
  • the plant species listed below were grown in 8.5cm square pots containing sterile loam in a glasshouse (minimum temperature 16°C, 16 hours per day photoperiod) , and were treated in a spray cabinet at the 2-3 leaf stage with the compounds of the Examples listed below formulated as a solution/suspension in 3:1 by volume of acetone and the wetting agent polyoxyethylene (20 mols) monolaurate solution (10 g per litre) . The concentration of each test compound and volume of application were calculated to give the desired rate of application of the compound in 200 litres per hectare.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

On décrit des dérivés d'acide acétique herbicides de formule (I) dans laquelle: R représente un groupe -CO2R1, -CH2OH, -CONHSO2Ra ou -CONHSO¿2? -NR?aRb¿, dans lequel R1 est de l'hydrogène ou représente un groupe formant un sel ou un ester, Ra est un alkyle ou un aryle, et Rb est de l'hydrogène, un alkyle ou un aryle; R2 et R3, qui peuvent être identiques ou différents, sont chacun un halogène, un alkyle, un alcoxy, un alkylthio, un alkylamino ou un dialkylamino; A est un aryle substitué ou non, un hétérocyclyle ou représente un groupe hétérocyclyle ou benzohétérocyclyle, ou un alkyle, un alcényle, un alcynyle, un cycloalkyle substitué ou non ou un groupe cycloalcényle; X est de l'oxygène ou du soufre; Y est -CH= ou -N=; et Z est de l'oxygène ou du soufre; ainsi que des sels desdits dérivés, des compositions herbicides contenant ceux-ci et des procédés de préparation et d'utilisation de ceux-ci.
PCT/GB1991/002167 1990-12-13 1991-12-06 Herbicides WO1992010484A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19904040118 DE4040118A1 (de) 1990-12-13 1990-12-13 Substituierte (alpha)-pyrimidinyloxy(thio)- und (alpha)-triazinyloxy(thio)essigsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung
DEP4040118.9 1990-12-13

Publications (1)

Publication Number Publication Date
WO1992010484A1 true WO1992010484A1 (fr) 1992-06-25

Family

ID=6420420

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1991/002167 WO1992010484A1 (fr) 1990-12-13 1991-12-06 Herbicides

Country Status (3)

Country Link
AU (1) AU9069391A (fr)
DE (1) DE4040118A1 (fr)
WO (1) WO1992010484A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0347811A1 (fr) * 1988-06-20 1989-12-27 Kumiai Chemical Industry Co., Ltd. Dérivés d'acides alcanoiques et compositions herbicides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0347811A1 (fr) * 1988-06-20 1989-12-27 Kumiai Chemical Industry Co., Ltd. Dérivés d'acides alcanoiques et compositions herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, , no. 115, 1991, Columbus, Ohio, US; abstract no. 280053N, page 1020 ;column 1 ; *

Also Published As

Publication number Publication date
DE4040118A1 (de) 1992-06-17
AU9069391A (en) 1992-07-08

Similar Documents

Publication Publication Date Title
EP0625970B1 (fr) Herbicides contenant des sulfonamides
EP0410590B1 (fr) Herbicides dérivés de pyrimidines
EP0244948A2 (fr) Herbicides de triazolopyrimidine
US5317005A (en) Pyrimidinyl and triazinyl herbicides
US5024693A (en) Herbicides
AU2945892A (en) Azole derivative herbicides and fungicides
AU1410292A (en) Herbicides
WO1992010484A1 (fr) Herbicides
US5604181A (en) Pyrimidine derivatives herbicides
US5502028A (en) Herbicidal pyrimidinyl or triazinyl haloacetic acid derivatives
KR940005023B1 (ko) 벤즈알데하이드 아세탈 화합물 및 이의 제조방법과 활성성분으로서 이를 포함하는 제초제 조성물
US5401710A (en) Herbicides

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BG BR CA CS FI HU JP KR PL RO SD SU US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE BF BJ CF CG CH CI CM DE DK ES FR GA GB GN GR IT LU MC ML MR NL SE SN TD TG

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载