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WO1998031226A1 - Agent herbicide - Google Patents

Agent herbicide Download PDF

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Publication number
WO1998031226A1
WO1998031226A1 PCT/EP1998/000163 EP9800163W WO9831226A1 WO 1998031226 A1 WO1998031226 A1 WO 1998031226A1 EP 9800163 W EP9800163 W EP 9800163W WO 9831226 A1 WO9831226 A1 WO 9831226A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
halogen
hydrogen
substituted
alkenyl
Prior art date
Application number
PCT/EP1998/000163
Other languages
German (de)
English (en)
Inventor
Jutta Glock
Elmar Kerber
Willy Rüegg
Original Assignee
Novartis Ag
Novartis-Erfindungen Verwaltungsgesellschaft Mbh
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 Novartis Ag, Novartis-Erfindungen Verwaltungsgesellschaft Mbh filed Critical Novartis Ag
Priority to AU62090/98A priority Critical patent/AU6209098A/en
Publication of WO1998031226A1 publication Critical patent/WO1998031226A1/fr

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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 new selective herbicidal compositions for controlling grasses and weeds in crops of useful plants, in particular in crops of cereals, maize,
  • the invention thus proposes a selective herbicidal composition which is characterized in that, in addition to customary inert formulation auxiliaries such as carriers, solvents and wetting agents, it is a mixture of active ingredients
  • X is the group -C (Q 1 ) (Q 2 ) -;
  • Y represents the group -C (0) -A
  • A is hydrogen, hydroxy, O " M + , OR 2 , NR 28 R 29 or together with Q 2 -O-;
  • R 22 and R 23 independently of one another hydrogen, halogen, CC 5 -alkyl, trifluoromethyl, -O-
  • R 22 and R 2 together form a butadienylene chain which is substituted by halogen, methyl, methoxy,
  • trifluoromethyl or trifluoromethoxy may be substituted and fused at positions 3 and 4;
  • R 59 and R 6 o independently of one another are hydrogen, halogen, CC 5 -alkyl, trifluoromethyl, -O-
  • Cycloalkyl nitro, amino, cyano, -COO-Q- alkyl, -NH-C C 5 alkyl, N (-C 5 alkyl) 2 , C 3 -
  • R 64 is hydrogen, -0- (C 1 -C 5 ) alkyl, -O- - -alkenyl, -O- - -alkynyl, CC 3 -haloalkoxy or Ci-Cs-alkyl;
  • R 65 C, -C 3 -alkyl, C 3 -C 5 -cycloalkyl, -0- (C) -alkyl, -OQQ-alkenyl, -OQQ-alkinyi, Q-
  • R JS is hydrogen, -0- (QC 5 ) alkyl, -OQQ-alkenyl, -OQQ-alkynyl, C, -C 5 -haloalkoxy or QQ-alkyl;
  • R 26 QQ-alkyl, C 3 -C 5 cycloalkyl, -0- (QQ) alkyl, -0-C 3 -C 5 alkenyl, -O- - -alkynyl, Q-
  • R 58 QQ alkyl, QQ alkenyl, C 3 -C 5 cycloalkyl, halogen or trifluoromethyl;
  • R 27 CC 8 alkyl, C -C 8 cycloalkyl, QQ alkenyl, QQ alkynyl, benzyl, C 1 -C 5 haloalkyl,
  • R 2g is hydrogen, -CC-alkyl, QQ-alkenyl or QQ-alkynyl;
  • R 29 is hydrogen, QQ-alkyl, QQ-alkenyl, QQ-alkynyl, or by halogen, cyano,
  • Phenyl pyridyl or benzyl; or the group in which for hydrogen,
  • QQ-alkyl QQ-alkenyl, phenyl, benzyl or QQ-alkynyl
  • R 62 for hydrogen, QQ- Alkyl, or by hydroxy, SCH 3 , SH, benzyl, indol-3-yl, 4-hydroxybenzyl, COOR ⁇ 3 ,
  • R_ 3 for hydrogen, Q-Cg-alkyl, QQ-alkenyl, QQ-alkynyl, -NH (QQ-alkyl), -N (QQ-
  • QQ-alkylthio, QC 5 -alkylsulfonyl, QQ-alkylsulfinyl, nitro, cyano or trifluoromethoxy may be substituted, morpholino or piperidino;
  • X 2 , X 3 and X 4 independently of one another oxygen or sulfur; p, q, r, s and t independently of one another 0, 1 or 2;
  • R 28 and R 2 9 together form a QQ alkylene chain which is substituted by halogen, methyl, methoxy,
  • trifluoromethyl or trifluoromethoxy may be substituted and may be interrupted by -O-, -NH- or -N (C 2 -Q-alkyl) -;
  • R 34 and R 5 0 independently of one another QQ-alkyl
  • R 34 and R 5 6 together form a C 2 -C 3 alkylene chain
  • R 57 QQ-AlkyL Q-Cg-alkoxy, Q-Cg-haloalkyl, Ci-Cg-haloalkoxy, C -C 8 cycloalkyl,
  • R 3 o, R 3 ⁇ , R 32 and R 33 independently of one another hydrogen, QQ-alkyl or QQ-alkyl substituted by hydroxy or methoxy; or
  • R 30 and R 3 ⁇ or R 30 , R 3 ⁇ and R 32 or R 30 , R 3 l , R 2 and R together form a QQ
  • Alkylene chain which can be interrupted by -O-, -NH- or -N (QQ-alkyl) - mean; and b) a herbicide-antagonistically effective amount of a safener of the formula Ha wherein Ri is hydrogen, Ci-Cg-alkyl or QQ-alkyl substituted by QQ-alkoxy or QQ-alkenyloxy and X is hydrogen or chlorine; of a safener of the formula
  • E is nitrogen or methine
  • R 3 is -CC1 3 or phenyl optionally substituted by halogen
  • R 4 and R 5 are independently hydrogen or halogen; a Formula He safener
  • R 6 and R 7 are independently hydrogen or halogen, and Rg, R9 and R 10 are independently C 1 -C 4 alkyl, a safener of the formula Ild wherein
  • R ⁇ 3 and R ⁇ independently of one another hydrogen, Ci-Cg-alkyl, C 3 -C 8 cycloalkyl, QQ-
  • R ⁇ 3 and R ⁇ 4 form together a QQ-Alkylenbrück ⁇ , which by oxygen, sulfur, SO, S0 2 , NH or -
  • N (Q-Qalkyl) - can be interrupted
  • Rn for hydrogen, halogen, cyano, trifluoromethyl, nitro, Q-Q-alkyl, Q-Q-alkoxy, Q-
  • R g for hydrogen, halogen, cyano, nitro, QQ-alkyl, QQ-haloalkyl, QQ-
  • R c represents hydrogen, halogen, nitro, QQ-alkyl or methoxy;
  • R ⁇ j for hydrogen, halogen, nitro, QQ-alkyl, QQ-alkoxy, Q-Qalkylthio, QQ-alkylsulfinyl, QQ-alkylsulfonyl, - COOR j or CONR k R m ;
  • R e for hydrogen, halogen, QQ-alkyl, -COOR J5 trifluoromethyl or methoxy, or R d and R ,, together form a QQ-alkylene bridge;
  • R f represents hydrogen, halogen or QQ alkyl;
  • R x and R y independently of one another for hydrogen, halogen, QQ-alkyl, QQ-alkoxy, Q-Q-alkylthio, -COOR 16 , trifluoromethyl, nitro or cyano;
  • R j , R and R m are independently hydrogen or QQ alkyl; or
  • R k and R m together form a Q-alkylene bridge which can be interrupted by oxygen, NH or -N (Q-Q-alkyl);
  • R n is QQ-alkyl, phenyl, or phenyl substituted by halogen, QQ-alkyl, methoxy, nitro or trifluoromethyl;
  • R 16 for hydrogen, Q-Qo-alkyl, QQ-alkoxy-QQ-alkyl, QQ-alkylthio-QQ-alkyl, di-QQ-alkylamino-QQ-alkyl, halogen-QQ-alkyl, C 2 -C 8 alkenyl , Halogen-C 2 -Cg-alkenyl, C 3 -C 8 -alkynyl, QQ-cycloalkyl, halogen-C -C 7 -cycloalkyl, Ci-Cg-alkylcarbonyl, allylcarbonyl, C 3 -C 7 -cycloalkylcarbonyl, benzoyl, the is unsubstituted or substituted on the phenyl ring, identically or differently, up to three times by halogen, QQ-alkyl, halogen-QQ-alkyl, halogen-QQ-alkoxy or QQ-alkoxy; or furoy
  • R 17 and R 18 are independently QQ alkyl or QQ alkenyl; or R- 17 and R ⁇ 8
  • R 3 and R 36 are independently hydrogen or QQ alkyl
  • R 37 and R 8 independently of one another for QQ-alkyl, or R 37 and R 38 together - (CH 2 ) r;
  • R 9 for hydrogen, QQ-alkyl or or R 7 and rig together for
  • R 20 is hydrogen or chlorine and R 19 is cyano or trifluoromethyl, or a safener of the formula Hg
  • R 2] is hydrogen or methyl.
  • the pictorial representation of the groups W , W and W 3 should be understood in such a way that the point of attachment to the substituent Y is always the upper free valence.
  • the linkage point to the substituent Y is in the ortho position to the substituent R 59 .
  • alkyl groups occurring in the substituent definitions are, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl and their branched Isomers.
  • Alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned.
  • the alkenyl and alkynyl radicals can be mono- or polyunsaturated.
  • Suitable cycloalkyl substituents contain 3 to 6 carbon atoms and are e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Halogen usually means fluorine, chlorine, bromine or iodine.
  • Haloalkyl and haloalkoxy groups can be substituted one or more times, with fluorine being preferred as halogen.
  • substituents such as -N (QQ-alkyl) 2 the alkyl radicals can be the same or different. They preferably have the same meaning.
  • R 62 is different from hydrogen, the group has a through *
  • labeled chiral center which particularly preferably has the configuration ⁇ S> of the naturally occurring L-amino acids.
  • A is hydrogen, hydroxy, O ' M ", OR 27 , NR 28 R 2 or together with Q 2 -O-;
  • R 22 and R 23 independently of one another hydrogen, halogen, QQ-alkyl, trifluoromethyl, -O-
  • -S (0) r CH trifluoromethyl or trifluoromethoxy may be substituted and fused at positions 3 and 4;
  • R 59 and R 60 independently of one another are hydrogen, halogen, QQ-alkyl, trifluoromethyl, -0- (QQ) -alkyl or QQ-cycloalkyl;
  • R 25 is hydrogen, -0- (QQ) -alkyl, -OQQ-alkenyl, -OQQ-alkynyl, difluoromethoxy or
  • R 26 QQ-alkyl, QQ-cycloalkyl, -0- (GQ) -alkyl, -OQQ-alkenyl, -OQQ-alkynyl,
  • R 58 independently of one another are QQ-alkyl, QQ-cycloalkyl, -0- (QQ) -alkyl, -OQQ-alkenyl, -OQQ-alkynyl, halogen or trifluoromethyl; or R_ 6 and Ei together -CH 2 -CH 2 -;
  • R 27 Ci-Cg-alkyl, QQ-cycloalkyl, QQ-alkenyl, QQ-alkynyl, benzyl, QQ-haloalkyl, Q -Q-haloalkenyl,
  • R 28 is hydrogen, QC 5 alkyl, QQ alkenyl or QQ alkynyl;
  • R 29 is hydrogen, Q-Cg-alkyl, QQ-alkenyl, QQ-alkynyl, or by halogen, -X 2 - (QQ-alkyl), hydroxy, amino, -NH (QQ-alkyl), N (QQ-alkyl) 2 or -CH (X 3 R 34 ) (X 4 R 5 6) substituted Q-Cg-alkyl, QQ-alkenyl or QQ-alkynyl; Phenyl, pyridyl or benzyl or phenyl, pyridyl or benzyl substituted by halogen, QQ-alkyl, QQ-haloalkyl, -S (0) p -QQ-alkyl, nitro, cyano or trifluoromethoxy; or the group
  • R ⁇ 1 is hydrogen, Q-Cg-alkyl, QQ-alkenyl or QQ-
  • R 62 for hydrogen, QQ-alkyl, or QC substituted by hydroxy, SCH 3 , SH, benzyl, indol-3-yl, 4-hydroxybenzyl, COOR, C (0) NH 2 , amino or imidazol-5-yl 5 alkyl; and R 63 represents hydrogen, Ci-Cg-alkyl, QQ-alkenyl or QQ-alkynyl; X 2 , X 3 and X4 independently of one another oxygen or sulfur; p, r, s and t independently of one another 0, 1 or 2;
  • R 28 and R 29 together form a QQ alkylene chain which can be substituted by halogen, methyl, methoxy, -S (0) s CH, trifluoromethyl or trifluoromethoxy and by -O-, -NH- or -N (QQ-alkyl) - can be interrupted;
  • R 34 and R 56 are independently QQ alkyl; or R 34 and R 56 together form a QQ alkylene chain; R 57 QQ-alkyl, QQ-cycloalkyl, QQ-alkenyl, QQ-alkynyl, phenyl or benzyl or substituted by halogen, QQ-alkyl, QQ-haloalkyl, -S (0) t -QQ-alkyl, nitro, cyano or trifluoromethoxy Phenyl or benzyl;
  • R 30 , R 3 ⁇ , R and R 33 independently of one another hydrogen, QQ-alkyl or QQ-alkyl substituted by hydroxy or methoxy; or R 30 and R 3] or R 30 , R 3 ⁇ and R 32 or R 30 , 3 ⁇ , 3 2 and R 33 together form a QQ alkylene chain which can be replaced by -O-, -NH- or -N (QQ- Alkyl) - can be interrupted.
  • W stands for W
  • R 5 9 is hydrogen, fluorine, chlorine or methoxy
  • R 50 is hydrogen, fluorine, or chlorine
  • Qi is hydrogen, hydroxy, OR 58 or -OC (0) -R 57 , and
  • R57 QQ-alkyl 5 QQ-alkenyl or QQ-alkynyl mean.
  • R 28 is hydrogen or methyl and R 29 is QQ-alkyl, QQ-alkenyl, QQ-alkynyl, or by halogen, -X 2 - (QQ-alkyl), hydroxy, Amino, -NH (QQ-alkyl), N (QQ-alkyl) 2 or
  • R ⁇ i is hydrogen, Q-Q-alkyl, Q-Q-alkenyl or Q-
  • R 62 for hydrogen, QQ-alkyl, or QQ substituted by hydroxy, SCH 3 , SH, benzyl, indol-3-yl, 4-hydroxybenzyl, CO0R 63 , C (0) NH 2 , amino, or imidazol-5-yl - alkyl; and R 6 represents hydrogen, QQ-alkyl, QQ-alkenyl or QQ-alkynyl; or b) R 5S is chlorine; R ⁇ o hydrogen; AO ' M + or together with Q 2 -O-; Qi is hydrogen, hydroxy or -OC (O) - Q-Cg-alkyl; and
  • M is Li + , Na + , K + , NH 3 + C-Cg-alkyl or NH 2 + (C 1 -C 8 alkyl) 2 .
  • Particularly preferred agents according to the invention contain a safener of the formula Ha, wherein Xi very particularly preferably represents chlorine and Ri represents -CH (CH 3 ) QHn (n).
  • the invention also relates to a process for the selective control of weeds in crops, which consists in that the crops, their seeds or cuttings or their cultivated area are treated simultaneously or separately with a herbicidally active amount of the herbicide of the formula I and a herbicidally antagonistically effective amount of the safener of the formulas Ha to Hg.
  • Cereals, maize, soybeans and rice, preferably cereals are particularly suitable as crop plants which can be protected against the damaging action of the herbicides mentioned by the safeners of the formulas Ha to Ilg. Cultures are also to be understood as those which have been made tolerant to herbicides or classes of herbicides by means of conventional breeding or genetic engineering methods.
  • the weeds to be combated can be both monocot and dicot weeds, such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
  • Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sid
  • the cultivated areas are the soil areas already overgrown with the crop plants or filled with the seeds of these crop plants, as well as the soils intended for cultivation with these crop plants.
  • a safener of the formula II can be used for the pretreatment of the seed of the crop (dressing the seed or the cuttings) or can be added to the soil before or after the seed. However, it can also be applied on its own or together with the herbicide after the plants have emerged.
  • the treatment of the plants or the seed with the safener can therefore in principle be carried out independently of the time of application of the herbicide. However, the treatment of the plant 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 largely depends on the type of application.
  • the ratio of herbicide to safener is generally from 100: 1 to 1:10, in particular from 10: 1 to 1: 1, preferably 5: 1 to 1: 1.
  • 0.001 to 5.0 kg of safener / ha are applied in the field treatment.
  • the application rates of herbicide are generally between 0.001 to 4 kg / ha, but preferably between 0.005 to 1 kg / ha.
  • the agents according to the invention are suitable for all application methods customary in agriculture, e.g. preemergent application, postemergent application and seed dressing suitable.
  • safener solutions which contain the active compound in a concentration of 1 to 10,000, preferably 100 to 1000 ppm.
  • the safeners of the formula II or combinations of these safeners with the herbicides of the formula I are expediently processed together with the auxiliaries customary in formulation technology, for example to emulsion concentrates, spreadable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
  • the formulations are prepared in a known manner, e.g. by intimately mixing and / or grinding the active ingredients with liquid or solid formulation auxiliaries, e.g. Solvents or solid carriers.
  • surface-active compounds surfactants
  • surfactants can also be used in the preparation of the formulations.
  • Aromatic hydrocarbons preferably the fractions Cg to Q 2 , such as xylene mixtures or substituted naphthalenes, phthalic acid esters such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols, and their ethers and esters such as ethanol Ethylene glycol Ethylene glycol monomethyl or ethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or N, N-dimethylformamide, and optionally epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; or water.
  • Aromatic hydrocarbons preferably the fractions Cg to Q 2 , such as xylene mixtures or substituted naphthalenes, phthalic acid esters such as dibutyl or dioctyl
  • solid carriers e.g. natural dust, such as calcite, talc, kaolin, montmorillonite or attapulgite
  • solid carriers e.g. natural dust, such as calcite, talc, kaolin, montmorillonite or attapulgite
  • highly disperse silica or highly disperse absorbent polymers e.g. Pumice stone, broken brick, sepiolite or bentonite, as non-sorptive carrier materials e.g. Calcite or sand in question.
  • a large number of pregranulated materials of inorganic or organic nature such as in particular dolomite or comminuted plant residues, can be used.
  • nonionic, cationic and / or anionic surfactants and surfactant mixtures with good emulsifying, dispersing and wetting properties are suitable as surface-active compounds.
  • Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.
  • the soaps are the alkali, alkaline earth or optionally substituted ammonium salts of higher fatty acids (Qo-C 22 ), such as the Na or K salts of oleic or stearic acid, or of natural fatty acid mixtures, for example from coconut or Tallow oil can be extracted.
  • Qo-C 22 the alkali, alkaline earth or optionally substituted ammonium salts of higher fatty acids
  • the soaps are the alkali, alkaline earth or optionally substituted ammonium salts of higher fatty acids (Qo-C 22 ), such as the Na or K salts of oleic or stearic acid, or of natural fatty acid mixtures, for example
  • the fatty alcohol sulfonates or sulfates are generally present as alkali, alkaline earth or optionally substituted ammonium salts and have an alkyl radical with 8 to 22 C atoms, alkyl also including the alkyl part of acyl radicals, for example the Na or Ca salt lignin sulfonic acid, dodecyl sulfuric acid ester or a fatty alcohol sulfate mixture made from natural fatty acids.
  • This subheading also includes the salts of sulfuric acid esters and sulphonic acids from fatty alcohol-ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid residue with 8-22 carbon atoms.
  • Alkylarylsulfonates are, for example, the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or a naphthalenesulfonic acid / formaldehyde condensation product.
  • Corresponding phosphates such as e.g. Salts of the phosphoric acid ester of a p-nonylphenol (4-14) ethylene oxide adduct or phospholipids in question.
  • Suitable nonionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylene phenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 10 carbon atoms in the alkyl radical of the alkylphenols.
  • nonionic surfactants are the water-soluble polyethylene oxide adducts containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups on polypropylene glycol, ethylene diaminopolypropylene glycol and alkyl polypropylene glycol with 1 to 10 carbon atoms in the alkyl chain.
  • the compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • nonionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • Fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate, are also suitable.
  • the cationic surfactants are primarily quaternary ammonium salts which contain at least one alkyl radical having 8 to 22 carbon atoms as N substituents and have low, optionally halogenated alkyl, benzyl or low hydroxyalkyl radicals as further substituents.
  • the salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyl trimethyl ammonium chloride or benzyl di (2-chloroethyl) ethyl ammonium bromide.
  • the herbicidal formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active compound mixture from the compound of the formula I with the compounds of the formulas Ha, üb, He, Ild, He, Ilf or Hg 1 to 99.9% by weight of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight of a surfactant.
  • concentrated agents are usually preferred as commercial goods, the end user generally uses diluted agents.
  • the agents can also contain other additives such as stabilizers e.g. optionally epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, e.g.
  • Seed dressing a) Dressing the seeds with an active ingredient of the formula II formulated as a wettable powder by shaking in a vessel until uniform distribution on the seed surface (dry dressing). About 1 to 500 g of active ingredient of the formula Ha, üb, He, Ild, Ile, Ilf or Hg (4 g to 2 kg of wettable powder) are used per 100 kg of seed.
  • the dressing of the seeds or the treatment of the germinated seedlings are naturally the preferred methods of application because the active ingredient treatment is completely based on the Target culture is aimed.
  • 1 to 1000 g antidote, preferably 5 to 250 g antidote, are used per 100 kg of seed, depending on the method, which also allows the addition of other active substances or micronutrients, to deviate upwards or downwards from the specified limit concentrations ( Repeat stain).
  • a liquid processing of a mixture of antidote and herbicide (mutual ratio between 10: 1 and 1: 100) is used, the amount of herbicide applied being 0.005 to 5.0 kg per hectare.
  • Such tank mixes are applied before or after sowing.
  • the safener is introduced into the open seeded furrow as an emulsion concentrate, wettable powder or as granules. After covering the furrow, the herbicide is applied in the pre-emergence process in the usual way.
  • the active substance of the formula Ha, üb, He, Ild, Ile, Ilf or Hg is applied in solution to mineral granulate carriers or polymerized granules (urea / formaldehyde) and dried. If necessary, a coating can be applied (coating granules), which allows the active ingredient to be dispensed in doses over a certain period of time.
  • preferred formulations are composed as follows:
  • Emulsifiable concentrates are:
  • Active ingredient mixture 1 to 90%, preferably 5 to 20% surface-active agent: 1 to 30%, preferably 10 to 20% liquid carrier: 5 to 94%, preferably 70 to 85%
  • Active ingredient mixture 0.1 to 10%, preferably 0.1 to 5% solid carrier: 99.9 to 90%, preferably 99.9 to 99% suspension concentrates:
  • Active ingredient mixture 5 to 75%, preferably 10 to 50% Water: 94 to 24%, preferably 88 to 30% surfactant: 1 to 40%, preferably 2 to 30%
  • Active ingredient mixture 0.5 to 90%, preferably 1 to 80% surface-active agent: 0.5 to 20%, preferably 1 to 15% solid carrier material: 5 to 95%, preferably 15 to 90%
  • Active ingredient mixture 0.1 to 30%, preferably 0.1 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%
  • the solutions are suitable for use in the form of tiny drops.
  • the active ingredient is mixed well with the additives and ground well in a suitable grinder.
  • Spray powder is obtained which can be mixed with water to form any desired suspension
  • Polyethylene glycol MG 200 1.0% 2% 3%
  • the finely ground active ingredient is evenly applied in a mixer to the carrier material moistened with polyethylene glycol. In this way you get dust-free
  • the active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in an air stream.
  • Ready-to-use dusts are obtained by mixing the active ingredient with the carrier substances and grinding them in a suitable mill.
  • Active ingredient mixture I with Ea, Eb, Ec, Ed, Ee, Ef or Eg 3% 10% 25% 50% Erhylenglykol 5% 5% 5% 5% 5%
  • the finely ground active ingredient is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water. It is often more practical to individually formulate the active ingredient of formula I and the mixing partner of the formula Ea, Eb, Ec, Ed, Ee, Ef or Eg and then bring them together in the desired mixing ratio in the applicator as a "tank mixture" in water shortly before application .
  • Particularly preferred agents according to the invention contain the compound no. 3.01 as safener and a compound selected from the compounds 2,090, 2,091, 2,065, 1,020, 1,013, 1,012, 2,054, 2,120, 2,122, 1,045, 2,034 and 2,042 as herbicide.
  • Example B1 Postemergent phytotoxic effect of the herbicides of the formula I and the mixtures of the herbicides with the safeners of the formula E on wheat: Wheat is grown in plastic pots up to the 4-leaf stage under greenhouse conditions. At this stage, the herbicides alone and the mixtures of the herbicides with the safeners are applied to the test plants. Application is carried out as an aqueous suspension of the test substances according to Example F8 with 500 l of water / ha. The application rates for the herbicides are 4000, 2000, 1000 and 500 g / ha, the application rate for the safeners is 60 g / ha. A percentage scale is used 14 days after the application. 100% means test plant is dead, 0% means no phytotoxic effect. The results show that the safeners significantly reduce the damage to the crop caused by the herbicides. Examples of the reduction in the phytotoxic action of the herbicides by the safeners of the formulas Ea to Ee are given in the following Table B1:
  • the application rate of the safener in the following table is 60 g ai / ha.

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un agent herbicide sélectif pour lutter contre les graminées et les mauvaises herbes dans les cultures de plantes agricoles, contenant: (a) une quantité efficace d'un herbicide de la formule (I), et (b) une quantité à action antagoniste d'herbicide d'un phytoprotecteur de formule (IIa), d'un phytoprotecteur de formule (IIb), d'un phytoprotecteur de formule (IIc), d'un phytoprotecteur de formule (IId), d'un phytoprotecteur de formule (IIe), d'un phytoprotecteur de formule (IIf) ou bien d'un phytoprotecteur de formule (IIg), dans lesquelles les substituants ont la signification donnée dans la revendication 1.
PCT/EP1998/000163 1997-01-15 1998-01-13 Agent herbicide WO1998031226A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU62090/98A AU6209098A (en) 1997-01-15 1998-01-13 Herbicidal agent

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH6897 1997-01-15
CH68/97 1997-01-15

Publications (1)

Publication Number Publication Date
WO1998031226A1 true WO1998031226A1 (fr) 1998-07-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/000163 WO1998031226A1 (fr) 1997-01-15 1998-01-13 Agent herbicide

Country Status (2)

Country Link
AU (1) AU6209098A (fr)
WO (1) WO1998031226A1 (fr)

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US7495103B2 (en) 2004-06-24 2009-02-24 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
EP2191716A1 (fr) * 2008-11-29 2010-06-02 Bayer CropScience AG Combinaison d'herbicide-phytoprotecteur
CN102283197A (zh) * 2011-08-05 2011-12-21 湖南人文科技学院 邻羟基苯甲酸内酯类化合物缓解酰胺类除草剂对水稻毒害的用途
US8354427B2 (en) 2004-06-24 2013-01-15 Vertex Pharmaceutical Incorporated Modulators of ATP-binding cassette transporters
US8410274B2 (en) 2005-12-28 2013-04-02 Vertex Pharmaceuticals Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
US8802700B2 (en) 2010-12-10 2014-08-12 Vertex Pharmaceuticals Incorporated Modulators of ATP-Binding Cassette transporters
US9701639B2 (en) 2014-10-07 2017-07-11 Vertex Pharmaceuticals Incorporated Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator
US9751839B2 (en) 2009-03-20 2017-09-05 Vertex Pharmaceuticals Incorporated Process for making modulators of cystic fibrosis transmembrane conductance regulator
US9782408B2 (en) 2014-10-06 2017-10-10 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
US10272046B2 (en) 2012-02-27 2019-04-30 Vertex Pharmaceuticals Incorporated Pharmaceutical composition and administrations thereof
US10570115B2 (en) 2016-09-30 2020-02-25 Vertex Pharmaceuticals Incorporated Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
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US10738030B2 (en) 2016-03-31 2020-08-11 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
US10793547B2 (en) 2016-12-09 2020-10-06 Vertex Pharmaceuticals Incorporated Modulator of the cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
US11179367B2 (en) 2018-02-05 2021-11-23 Vertex Pharmaceuticals Incorporated Pharmaceutical compositions for treating cystic fibrosis
US11253509B2 (en) 2017-06-08 2022-02-22 Vertex Pharmaceuticals Incorporated Methods of treatment for cystic fibrosis
US11414439B2 (en) 2018-04-13 2022-08-16 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
US11434201B2 (en) 2017-08-02 2022-09-06 Vertex Pharmaceuticals Incorporated Processes for preparing pyrrolidine compounds
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WO1994000987A2 (fr) * 1992-07-08 1994-01-20 Ciba-Geigy Ag Composition herbicide selective
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WO1996022022A1 (fr) * 1995-01-19 1996-07-25 Novartis Ag Composition herbicide
US5561101A (en) * 1990-06-07 1996-10-01 Sandoz Ltd. Substituted phthalides and heterocyclic phthalides

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US5561101A (en) * 1990-06-07 1996-10-01 Sandoz Ltd. Substituted phthalides and heterocyclic phthalides
EP0521407A1 (fr) * 1991-06-29 1993-01-07 Hoechst Schering AgrEvo GmbH Nouveaux mélanges d'herbicides et d'antidotes
WO1994000987A2 (fr) * 1992-07-08 1994-01-20 Ciba-Geigy Ag Composition herbicide selective
DE4310220A1 (de) * 1993-03-30 1994-10-06 Basf Ag Herbizide Mittel, enthaltend einen oder mehrere herbizide Wirkstoffe aus der Gruppe der Salizylsäurederivate und ein oder mehrere antidotisierend wirkende Verbindungen
WO1996022022A1 (fr) * 1995-01-19 1996-07-25 Novartis Ag Composition herbicide

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