EP0804077A1 - Herbizide zusammensetzung - Google Patents

Herbizide zusammensetzung

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Publication number
EP0804077A1
EP0804077A1 EP96900566A EP96900566A EP0804077A1 EP 0804077 A1 EP0804077 A1 EP 0804077A1 EP 96900566 A EP96900566 A EP 96900566A EP 96900566 A EP96900566 A EP 96900566A EP 0804077 A1 EP0804077 A1 EP 0804077A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
halogen
substituted
hydrogen
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP96900566A
Other languages
English (en)
French (fr)
Inventor
Jutta Glock
Elmar Kerber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Novartis AG
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 Ciba Geigy AG, Novartis AG filed Critical Ciba Geigy AG
Publication of EP0804077A1 publication Critical patent/EP0804077A1/de
Withdrawn legal-status Critical Current

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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
    • A01N43/48—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

Definitions

  • the present invention relates to a selective-herbicidal composition for controlling grasses and broad-leaved weeds in crops of useful plants, in particular in crops of maize and cereals such as rye, barley, oats and, in particular, wheat, which composition comprises a herbicide and a safener (counteracting agent, antidote) and which safeguards the useful plants, but not the weeds, against the phytotoxic effect of the herbicide, and to the use of this composition for weed control in crops of useful plants.
  • a herbicide and a safener counteracting agent, antidote
  • safeners which are capable of antagonizing the damaging effect of the herbicide on the crop plant, i.e. of protecting the crop plant from this effect while causing virtually no impairment of the herbicidal effect on the weeds to be controlled.
  • the safeners proposed often have a very specific action both with regard to the crop plants and with regard to the herbicide and in some cases, in addition, depending on the mode of application; in other words, a particular safener is often suitable only for a specific crop plant and a specific class of herbicidal substance, or a specific herbicide.
  • a selective-herbicidal composition which comprises, in addition to customary inert formulation auxiliaries such as carriers, solvents and wetting agents, an active substance comprising a mixture of
  • Z is C r C 10 alkyl, C r C 10 alkyl substituted by halogen, C 3 -C 8 cycloalkyl, R 7 O-, R 7 S(O) n -,
  • R 7 R 8 N-, R 8 CO-, R 9 ON CR 8 -, (CH 3 ) 3 Si-, -CN or oxiranyl, CV alkenyl, C 2 -C 8 alkenyl substituted by halogen, phenyl, phenyl substituted by halogen, C r C 6 alkyl,
  • R 8 CO- or R 9 ON CR 8 -, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyl substituted by halogen, C C j ⁇ alkyl, phenyl, phenyl substituted by halogen, C r C 6 alkyl, C r C 6 haloalkyl,
  • R 7 is hydrogen, C r Cj 0 alkyl, C 2 -C 8 alkenyl, C -C 8 alkynyl, phenyl or phenyl substituted by halogen, Cj-Cgalkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy or C r C 6 -alkoxy- carbonyl, n is 0, 1 or 2,
  • R 8 is as defined for R 7 or is C C 6 alkoxy, C 3 -C 8 alkenyloxy or C 3 -C 8 alkynyloxy,
  • K is C C ⁇ alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkynyl
  • R 10 is C r C ⁇ 0 alkyl, C r C 10 alkyl substituted by halogen, R 7 O-, R 7 S(O) n -, -NR 7 R 8 or -CN,
  • R 5 is C r C 10 alkyl, C r C 10 alkyl substituted by halogen, C 3 -C 8 cycloalkyl, R 7 O-, R 7 S(O) n -,
  • R 7 R 8 N-, R 8 CO-, R 9 ON CR 8 -, (CH 3 ) 3 Si-, -CN or oxiranyl, C 2 -C 8 alkenyl, C 2 -C 8 alkenyl substituted by halogen, phenyl, phenyl substituted by halogen, C r C 6 alkyl,
  • R 6 is as defined for R 5 or is hydrogen or together with R 5 forms a C -C 7 alkylene radical, or
  • R 50 is hydrogen, halogen, -NO 2 , -CN, C ⁇ -C 4 alkyl substituted by halogen,
  • Rgo is hydrogen, halogen, -CN, -NO 2 , C C 4 alkyl, C]-C 4 alkyl substituted by halogen,
  • R 70 independently at each occurrence is hydrogen, C ] -C 4 alkyl
  • R 80 is hydrogen, C r C 4 alkyl, C ] -C 4 haloalkyl, halogen, -CO 2 R ⁇ 30 , -SO 2 NR 140 R 150 , -OSO 2 R 170 , -S(O) b R, 80 , -CN or -NO 2 , and
  • R-JO is hydrogen, C r C 4 alkyl, C r C 4 alkyl substituted by halogen or phenyl, C 2 -C 4 alkenyl, phenyl or phenyl substituted by halogen, C r C 4 alkyl, -NO , -CN or C r C 4 alkoxy, where
  • R 100 is hydrogen, C r C 4 alkyl, C r C 4 alkyl substituted by halogen or -OCH 3 ,
  • R 110 and R 12 o independently of one another are C r C 4 alkyl or R 1]0 and R 12 o together are
  • R 130 is hydrogen, C r C 4 alkyl, C r C 4 alkyl substituted by halogen, -CN, -CO 2 R 100 ,
  • R 1 0 is hydrogen or C r C 4 alkyl
  • R 1 0 is hydrogen, C r C 4 alkyl, C r C 4 alkoxy or C 2 -C 4 alkenyl, or R 140 and R 150 together are
  • R 160 is C r C 4 alkyl or C r C 4 haloalkyl
  • R 170 is Cj-C 4 alkyl or -NR- ⁇ oR- ⁇ o- in which R 140 and R 150 are as defined,
  • R 180 is C r C 4 alkyl, C r C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkenyl, C 3 -C 4 alkynyl, phenyl or phenyl substituted by halogen, C]-C 3 alkyl, C r C 3 alkoxy or C C 3 haloalkyl,
  • R 190 is C r C 4 alkyl or C r C 4 alkyl substituted by -F, -Cl or -OR 160 , q is 0 or 1,
  • G is a radical of the formula
  • R 260 is hydrogen or C--C 3 alkyl and R 270 is hydrogen, C r C 3 alkyl or C 2 -C 4 alkenyl,
  • R 2 is hydrogen, C r C 10 alkyl, - oalkyl substituted by C r C 6 alkoxy or Ci-Cgalkoxycarbonyl, C 3 -C 8 alkenyl or benzyl,
  • R 3 or R 4 together with R, form a radical -OCH 2 CH 2 (CH 2 ) m - or -(CH 2 ) m CH 2 CH 2 O-, in which m is 0 or 1 ,
  • R a is hydrogen, C C 8 alkyl, C C 8 alkyl substituted by hydroxy, C r C 8 alkoxy, phenoxy, Cj-Cgalkylthio, phenylthio, (CH 3 ) 3 Si- 1 C 3 -C 8 cycloalkyl, phenyl or di-Cj-Cgalkylamino, C 2 -C alkenyl, C 2 -C 6 alkenyl substituted by halogen, or R a is C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl substituted by C C 3 alkyl, or R a is C 3 -C 6 cycloalkenyl, phenyl, phenyl substituted by C ⁇ -C 8 alkyl, halogen, nitro, -CN, Cj- alkoxy, Cj-Cghaloalkoxy, phenoxy, -NR 7 R 8 or R
  • R a and R b together with the carbon atom to which they are attached, form a radical of the formula -CO-, and m is O or 1; and also salts and stereoisomers of the compounds of the formula I and
  • Ro j o is hydrogen, C r C 8 alkyl or C r C 8 alkyl which is substituted by C r C 6 alkoxy or
  • X 2 is hydrogen or chlorine, of a compound of the formula Ilbj
  • E is nitrogen or methine
  • Rn is -CC1 3 or unsubstituted or halogen-substituted phenyl
  • R 12 and R 13 independently of one another are hydrogen or halogen
  • R 14 is C r C 4 alkyl, of a compound of the formula IIb
  • R 12 and R 13 are as defined above, and
  • R 66 , R ⁇ -; and R 68 independently of one another are C r C 4 alkyl, of a compound of the formula He
  • R* 25 and R 26 independenriy of one another are hydrogen, Cj-Cgalkyl, C 3 -C 8 cycloalkyl,
  • R 1 and R 2 together form a C -Cgalkylene bridge which can be interrupted by oxygen, sulfur, SO, SO 2 , NH or -N ⁇ - alkyl)-,
  • R 27 is hydrogen or - alkyl
  • R ⁇ is hydrogen, halogen, cyano, trifluoromethyl, nitro, C ⁇ -C alkyl, C ⁇ -C 4 alkoxy,
  • R g is hydrogen, halogen, cyano, nitro, C r C alkyl, C r C 4 haloalkyl, C r C alkylthio,
  • R bb and R h independently of one another are hydrogen, halogen, C C 4 alkyl, trifluoromethyl, C r C 6 alkoxy, C r C 6 alkylthio or -COORJ;
  • R c is hydrogen, halogen, nitro, C--C alkyl or methoxy;
  • R d is hydrogen, halogen, nitro,
  • R e is hydrogen, halogen, C r C 4 alkyl, -COOR j , trifluoromethyl or methoxy, or R d and R e together form a C 3 -C 4 alkylene bridge;
  • R f is hydrogen, halogen or C r C 4 alkyl
  • R x and R y independently of one another are hydrogen, halogen, Cj-C 4 alkyl, C r C 4 alkoxy,
  • R j , R k and R m independently of one another are hydrogen or or
  • R k and R m together form a C 4 -C 6 alkylene bridge, which can be interrupted by oxygen, NH or -N(C r C 4 alkyl)-;
  • R_ is Cj-C 4 alkyl, phenyl, or phenyl which is substituted by halogen, C r C alkyl, methoxy, nitro or trifluoromethyl;
  • R 28 is hydrogen, C r C 10 alkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C r C 4 alkylthio-C r C 4 alkyl, di-
  • C 3 -C 7 cycloalkylcarbonyl benzoyl which is unsubstituted or is substituted on the phenyl ring by up to three identical or different substituents consisting of halogen, C r C 4 alkyl, halo-C r C alkyl, halo-C r C 4 alkoxy or C r C alkoxy; or furoyl, thienyl; or C r C 4 alkyl substituted by phenyl, halophenyl, C r C alkylphenyl, C r C alkoxyphenyl, halo-C r C 4 - alkylphenyl, halo-C r C 4 alkoxyphenyl, C ] -C 6 alkoxycarbonyl, C r C alkoxy-C 1 -C 8 - alkoxycarbonyl, C 3 -C 8 alkenyloxycarbonyl, C 3 -C 8 alkynyloxycarbon
  • R 33 and R 34 independently of one another are C r C 6 alkyl or C 2 -C 6 alkenyl; or R 33 and R-
  • R 35 and R 36 independently of one another are hydrogen or C r C 6 alkyl
  • R 39 ⁇ or R 33 and R ⁇ together are °
  • R 37 and R 38 independently of one another are C C 4 alkyl, or R 37 and R 38 together are -(CH 2 ) 5 - ;
  • R 39 is hydrogen, C r C 4 alkyl or (T il
  • R-40 R4I' R42' R 3' R44' R45' R46' R 7' R48' R49' ⁇ 5 ⁇ »
  • R5I' R52' R53' R54 and R55 independently of one another are hydrogen or C C 4 alkyl; of a compound of the formula Ilf
  • R 63 is hydrogen or chlorine and R 4 is cyano or trifluoromethyl, or of a compound of the formula Ilg
  • R 65 is hydrogen or methyl.
  • the invention also relates to a process for the selective control of weeds in crops of useful plants, which comprises treating the useful plants, their seeds or seedlings or their cultivation area, simultaneously or separately, with a herbicidally effective quantity of a herbicide of the formula I and a herbicide-antagonistically effective quantity of a safener of one of the formulae Ha to Ilg.
  • crops which can be protected by the safeners of the formulae Ila to Ilg against the damaging effect of the abovementioned herbicides
  • maize and cereals such as rye, barley, oats and, in particular, wheat are particularly suitable.
  • crops should also be understood as referring to those which have been made tolerant to herbicides or classes of herbicide by means of conventional breeding or genetic manipulation methods.
  • the weeds to be controlled may be both monocotyledon and dicotyledon weeds.
  • the areas regarded as cultivation areas are the soil areas on which the crop plants are already growing, or soil areas sown with the seed of these crop plants, and also the areas intended for cultivation with these crop plants.
  • alkyl groups mentioned in the definitions of substituents of the compounds of the formulae I and Ha to Ilg can be straight-chain or branched and are for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and also pentyl, hexyl, heptyl, octyl, nonyl, decyl and branched isomers thereof.
  • Suitable alkoxy, thioalkyl, haloalkyl and haloalkoxy groups are derived from the alkyl groups mentioned.
  • Examples of unsaturated substituent groups are ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl and isomers, which differ in the different position of the unsaturated bond or bonds in the molecule, isomers which include branching points, and cis and trans isomers in the case of the alkenes.
  • chlorine-substituted propenyl can exist in the two forms
  • substituted compounds of the formula I also constitute isomers which can be obtained and/or employed in pure form or as a mixture.
  • alkenyloxy, alkynyloxy, haloalkenyl and haloalkenyloxy groups can be derived from the alkyl groups mentioned.
  • Cycloalkyl groups comprise, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Corresponding cycloalkenes can be mono- or polyunsaturated.
  • substituted refers, where possible in the corresponding group, not only to monosubstitution but also to polysubstitution.
  • the invention likewise embraces agriculturally compatible salts which the compounds of the formula I can form, for example, with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
  • alkali metal and alkaline earth metal hydroxides as salt formers, particular emphasis should be placed on the hydroxides of lithium, sodium, potassium, magnesium or calcium, but especially on those of sodium or potassium.
  • amines suitable for forming ammonium salts are not only ammonia but also primary, secondary and tertiary C--C 18 alkylamines, C r C 4 hydroxyalkylamines and C 2 -C alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, eth
  • compositions according to the present invention comprise as herbicide a compound of the formula I in which R 3 and R are methoxy.
  • compositions comprise as herbicide a compound of the formula I in which R 3 and R 4 are methoxy and Z is Cj-Cjoalkyl, C 2 -C 8 alkenyl or C 2 -C 8 haloalkenyl.
  • compositions comprise as safener as compound of the formula Ha, Hb j , ⁇ b 2 or He.
  • Safeners which arc particularly suitable for use in the compositions according to the invention arc listed in the following tables.
  • a safener of the formulae Ila to Ilg can be used for pretreating the seed of the crop plant (dressing of the seed or of the seedlings), or placed in the soil before or after sowing. It can, however, also be applied, on its own or together with the herbicide, following the emergence of the plants.
  • the treatment of the plants or of the seed with the safener can therefore, in principle, take place independenriy of the point in time of the application of the herbicide.
  • the plant treatment can also be carried out by simultaneous application of herbicide and safener (for example as a tank mix).
  • the application rate of safener to herbicide to be applied depends largely on the method of application.
  • the ratio of herbicide to safener is in general from 1: 100 to 1:1 , preferably from 1 :50 to 1:5.
  • the application rates of herbicide are generally between 0.001 and 2 kg/ha, but preferably between 0.005 and 1 kg/ha.
  • compositions according to the invention are suitable for all application methods which are customary in agriculture, for example preemergence application, postemergence application and seed dressing.
  • safener/kg of seed In general, in seed dressing, from 0.001 to 10 kg of safener/kg of seed, preferably from 0.05 to 2 g of safener/kg of seed, are applied. If the safener is applied in liquid form shortly before sowing, accompanied by seed swelling, then it is expedient to use safener solutions which comprise the active substance in a concentration of from 1 to 10000 ppm, preferably from 100 to 1000 ppm.
  • the safeners of the formula II are advantageously processed together with the auxiliaries which are customary in the art of formulation to give particular formulations, for example emulsion concentrates, brushable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
  • the formulations are produced in a known manner, for example by intimate mixing and/or grinding of the active substances with liquid or solid formulation auxiliaries such as, for example, solvents or solid carriers.
  • surface-active compounds surfactants
  • Suitable solvents can be aromatic hydrocarbons, preferably Cg to C J2 fractions, for example xylene mixtures or substituted naphthalenes, phthalates such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols, and ethers and esters thereof, such as ethanol, diethylene glycol, 2-methoxyethanol or 2-ethoxyethanol, ketones, such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and unmodified or epoxidized vegetable oils, such as epoxidized coconut oil or soya oil; or water.
  • aromatic hydrocarbons preferably Cg to C J2 fractions, for example xylene mixtures or substituted naphthalenes, phthalates such as dibutyl or dioctyl phthalate, alipha
  • solid carriers for example for dusts and dispersible powders, use is generally made of ground natural minerals, such as calcite, talc, kaolin, montmorillonite or attapulgite.
  • ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite.
  • highly disperse silica or highly disperse absorbent polymers In order to improve the physical properties of the formulation, it is also possible to add highly disperse silica or highly disperse absorbent polymers.
  • Suitable granulated, adsorptive granule carriers are porous types, for example pumice, broken brick, sepiolite or bentonite, while suitable nonsorbent carrier materials are, for example, calcite or sand.
  • Suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. References to surfactants also include surfactant mixtures.
  • Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds.
  • Soaps which may be mentioned are the alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts of higher fatty acids (CI Q -C 2 ), for example the sodium or potassium salts or oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, for example, from coconut oil or tallow oil.
  • Other salts which can be mentioned are the fatty acid methyltaurine salts.
  • so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
  • the fatty sulfonates or fatty sulfates are generally present as alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts and have an alkyl radical of 8 to 22 carbon atoms, alkyl also including the alkyl moiety of acyl radicals, examples being the sodium or calcium salt of ligninsulfonic acid, of dodecylsulfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. Also included here arc the salts of sulfuric esters and sulfonic acids with fatty alcohol-ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid radical having 8 to 22 carbon atoms.
  • alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic acid-formaldehyde condensation product.
  • phosphates for example salts of the phosphoric ester of a p-nonylphenol-(4-14)-ethylene oxide adduct or phospholipids.
  • Suitable nonionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical, and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
  • nonionic surfactants are the water-soluble adducts, containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups, of polyethylene oxide and polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain.
  • the compounds mentioned customarily contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • nonionic surfactants which can be mentioned are nonylphenolpolyethoxy- ethanols, castor oil polyglycol ethers, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxy- ethanol.
  • fatty acid esters of polyoxyethylenesorbitan such as polyoxyethylenesorbitan trioleate .
  • the cationic surfactants are primarily quaternary ammonium salts which have, as N-substituent, at least one alkyl radical having 8 to 22 carbon atoms and, as further substituents, lower, unmodified or halogenated alkyl, benzyl or lower hydroxyalkyl radicals.
  • the salts arc preferably in the form of halides, methyl sulfates or ethyl sulfates, for example the stearyltrimethylammonium chloride or the benzyldi(2-chloroethyl)ethyl- ammonium bromide.
  • the agrochemical formulations generally contain from 0.1 to 99 per cent by weight, in particular from 0.1 to 95 % by weight, of safener or safener/herbicide active-substance mixture, from 1 to 99.9 % by weight, in particular from 5 to 99.8 % by weight, of a solid or liquid formulation auxiliary, and from 0 to 25 % by weight, in particular from 0.1 to 25 % by weight, of a surfactant.
  • While the preferred commercial product usually comprises concentrated compositions, the end user generally employs dilute compositions.
  • compositions can also comprise further additives, such as stabilizers, defoamers, viscosity regulators, binders, adhesives and fertilizers or other active substances.
  • Seed dressing a) The seeds are dressed by shaking them, in a vessel, together with an active substance of the formulae Ha to Ilg formulated as a wettable powder, until the active ingredient is distributed uniformly on the seed surface (dry seed dressing). In this case from about 1 to 500 g of active substance of the formulae Ha to Ilg (4 g to 2 kg of wettable powder) are used per 100 kg of seed.
  • the seeds are dressed by immersing them into a liquor containing 100-1000 ppm of active substance of the formulae Ha to Ilg for from 1 to 72 hours and then, if desired, by drying the seeds (seed soaking).
  • the dressing of the seed and the treatment of the seedling which has begun to germinate are of course the preferred methods of application, since the treatment with the active substance is directed entirely towards the target crop.
  • a liquid preparation of a mixture of antidote and herbicide (mutual quantitative ratio between 10:1 and 1:100) is used, the application rate of herbicide being from 0.005 to 5.0 kg per hectare.
  • Such tank mixes are applied before or after sowing.
  • the safener is introduced into the open seed drill, containing seed, as an emulsion concentrate, wettable powder or in the form of granules. After the seed drill has been covered over, the herbicide is applied preemergence in a customary manner.
  • the active substance of the formulae Ila to Ilg is applied in solution to mineral granule carriers or polymerized granules (urea/formaldehyde), which are then dried. If desired, a coating can be applied (coated granules), which enables the release of the active substance in regulated amounts over a defined period.
  • Active substance mixture 5 % 10 % 25 % 50 %
  • Active substance mixture 5 % 10 % 50 % 90 % l-Methoxy-3-(3-methoxypropoxy)- propane 20 % 20 %
  • Aromatic hydrocarbon mixture 75 % 60 %
  • the active substance is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. Wettable powders are obtained which can be diluted with water to give suspensions of any desired concentration.
  • Active substance mixture 0.1 % 5 % 15
  • the active substance is dissolved in methylene chloride, the solution is sprayed onto the carrier, and the solvent is subsequently evaporated off in vacuo.
  • the finely ground active substance is applied uniformly in a mixer to the carrier material which has been wetted with polyethylene glycol. Dust-frce coated granules are obtained in this way.
  • Active substance mixture 0.1 % 3 % 5 % 15 %
  • the active substance is mixed with the additives, and the mixture is ground and wetted with water. This mixture is extruded and subsequently dried in a stream of air.
  • Kaolin Ready-to-use dusts are obtained by mixing the active substance with the carriers and grinding the mixture in a suitable mill.
  • the finely ground active substance is intimately mixed with the additives.
  • a suspension concentrate is obtained from which, by dilution with water, suspensions of any desired concentration can be produced.
  • Example B 1 Postemergence applications of mixtures of a herbicide of the formula I with a safener of the formulae Ila to Ilg to cereals
  • Example B2 Postemergence applications of mixtures of a herbicide of the formula I with a safener of the formulae Ila to Ilg to maize
  • Table B5 Herbicidal action of the compounds of the formula I and a mixture thereof with the safeners of the formula 11 in maize S .
  • Example B3 Postemergence applications of mixtures of a herbicide of the formula I with a safener of t e formulae Ila to Ilg to rice
  • test plants Under greenhouse conditions, the test plants are sown or planted in plastic troughs in standard soil. Water is then introduced up to the surface of the soil. After 3 days, the water level is elevated by 2 cm and the herbicide is applied as an aqueous suspension (Example F7) on its own and in a tank mix with the safeners.
  • the application rates for the herbicide can be seen from Table B6.
  • the application rate for the safener is 125 g/ha. Cultivation of the test plants is then continued in the greenhouse under optimum conditions. 13 days after application, the test is evaluated using a percentage scale. 100 % denotes that the test plant has died, while 0 % denotes no phytotoxic effect. The results obtained show that, with the safeners of the formulae Ha to Ug, the damage caused to rice by the herbicide of the formula I can be substantially reduced.
  • Table B6 Herbicidal action of the compounds of the formula I and a mixture thereof with the safeners of the formula II in rice

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  • 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)
EP96900566A 1995-01-19 1996-01-05 Herbizide zusammensetzung Withdrawn EP0804077A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH14595 1995-01-19
CH145/95 1995-01-19
PCT/EP1996/000032 WO1996022022A1 (en) 1995-01-19 1996-01-05 Herbicidal composition

Publications (1)

Publication Number Publication Date
EP0804077A1 true EP0804077A1 (de) 1997-11-05

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EP96900566A Withdrawn EP0804077A1 (de) 1995-01-19 1996-01-05 Herbizide zusammensetzung

Country Status (10)

Country Link
EP (1) EP0804077A1 (de)
JP (1) JPH10512272A (de)
AR (1) AR000734A1 (de)
AU (1) AU4437296A (de)
BR (1) BR9607487A (de)
CA (1) CA2209902A1 (de)
IL (1) IL116797A0 (de)
PL (1) PL321244A1 (de)
WO (1) WO1996022022A1 (de)
ZA (1) ZA96400B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998031226A1 (de) * 1997-01-15 1998-07-23 Novartis Ag Herbizides mittel
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CA3019380A1 (en) 2016-03-31 2017-10-05 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
CN109803962B (zh) 2016-09-30 2022-04-29 弗特克斯药品有限公司 囊性纤维化跨膜传导调控蛋白的调节剂、以及药物组合物
MD3551622T2 (ro) 2016-12-09 2021-03-31 Vertex Pharma Modulator al regulatorului conductanței transmembranare în fibroză chistică, compoziții farmaceutice, metode de tratament și procedeu pentru fabricarea modulatorului
US11253509B2 (en) 2017-06-08 2022-02-22 Vertex Pharmaceuticals Incorporated Methods of treatment for cystic fibrosis
MA49631A (fr) 2017-07-17 2020-05-27 Vertex Pharma Méthodes de traitement de la fibrose kystique
JP7121794B2 (ja) 2017-08-02 2022-08-18 バーテックス ファーマシューティカルズ インコーポレイテッド ピロリジン化合物を調製するためのプロセス
WO2019079760A1 (en) 2017-10-19 2019-04-25 Vertex Pharmaceuticals Incorporated CRYSTALLINE FORMS AND COMPOSITIONS OF CFTR MODULATORS
EP3720849A2 (de) 2017-12-08 2020-10-14 Vertex Pharmaceuticals Incorporated Verfahren zur herstellung von cftr-regulatoren
TWI810243B (zh) 2018-02-05 2023-08-01 美商維泰克斯製藥公司 用於治療囊腫纖化症之醫藥組合物
EP3774825A1 (de) 2018-04-13 2021-02-17 Vertex Pharmaceuticals Incorporated Modulatoren des transmembranleitfähigkeitsreglers von zystischer fibrose, pharmazeutische zusammensetzungen, behandlungsverfahren und verfahren zur herstellung des modulators

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