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WO1995006642A1 - 1,3,5-triazin-diamines substituees par malodinitrile a effet herbicide - Google Patents

1,3,5-triazin-diamines substituees par malodinitrile a effet herbicide Download PDF

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Publication number
WO1995006642A1
WO1995006642A1 PCT/EP1994/002790 EP9402790W WO9506642A1 WO 1995006642 A1 WO1995006642 A1 WO 1995006642A1 EP 9402790 W EP9402790 W EP 9402790W WO 9506642 A1 WO9506642 A1 WO 9506642A1
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Prior art keywords
alkyl
formula
substituted
halogen
malodinitrile
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PCT/EP1994/002790
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German (de)
English (en)
Inventor
Gunther Beck
Helmut Heitzer
Bernd Baasner
Markus Dollinger
Hans-Joachim Santel
Original Assignee
Bayer Aktiengesellschaft
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Filing date
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Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU75366/94A priority Critical patent/AU7536694A/en
Publication of WO1995006642A1 publication Critical patent/WO1995006642A1/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
    • A01N43/64—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
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms

Definitions

  • the invention relates to the new malodinitrile-substituted 1,3,5-triazine diamines, several processes and new intermediates for their preparation and their use as herbicides.
  • 1,3,5-triazine derivatives can be used as herbicides.
  • 6-chloro-N-ethyl-N , -isopropyl- [1,3,5] triazine-2,4-diamine (atrazine) which is known to be used for weed control in maize crops, has gained particular practical importance (See, for example, "Chemistry of Plant Protection Products and Pest Control", Volume 5 - Herbicides, edited by R. Wegler, Springer-Verlag Berlin, Heidelberg, New York, 1977, pages 336-352).
  • Atrazine is against millet-like grasses, e.g. Echinochloa, Digitaria, Setaria etc. not or not fully effective.
  • R 1 and R ⁇ are the same or different and represent alkyl, cycloalkyl, alkoxyalkyl, cyanoalkyl, haloalkyl or phenylalkyl optionally substituted by halogen or alkyl and Z represents a saturated or unsaturated aliphatic radical, phenylalkyl optionally substituted by halogen or phenyl optionally substituted by halogen
  • R2 has the meaning given above
  • Rl and Z have the meaning given above, with the approximately equimolar amount of an amine of the formula (V)
  • R2 has the meaning given above
  • the active compounds according to the invention have a better selective action and a broader spectrum of action than the previously known 1,3,5-triazine diamines.
  • the active compounds according to the invention are considerably more effective against certain harmful grasses than the previously known atrazine.
  • Rl and R- are the same or different and for C j -Cg-alkyl, C3-C6-cycloalkyl, C ⁇ - C4-alkoxy-C2-C4-alkyl, cyano-C ⁇ -C4-alkyl, fluoro-C2-Cg- alkyl with 1 to 9 F-
  • Z is Ci-Cg-alkyl, C2-Cg-alkenyl, C2-Cg-alkynyl, optionally halogen-substituted phenyl -CC-C4-alkyl or optionally halogen-substituted phenyl.
  • R * and R2 are identical or different and for C1-C4-alkyl, C3-C4-cycloalkyl, C ⁇ -
  • Z stands for Cj-Cg-alkyl, C2-C6-alkenyl, C2-C (5-alkynyl, optionally chlorine-substituted phenyl -CC-C2-alkyl or optionally chlorine-substituted phenyl.
  • Rl and R2 are the same or different and are C1-C4-alkyl, C3-C4-cycloalkyl or fluoro-C2-C4-alkyl having 1 to 4 F atoms and
  • Z represents C1-C4-alkyl
  • halogen-1,3,5-triazine diamines of the formula (II) used as starting compounds in process A are known and / or can be prepared by known processes (cf., for example, DE-A-32 18 966; DE-A- 39 00300; EP-A-73 974).
  • the 2-substituted malodinitrile derivatives of the formula (HI) used as starting compounds in process A are also known or can be prepared by methods known in principle.
  • the malodinitrile-substituted halo-1,3,5-triazine amines of the formula (IV) used as starting compounds in process B are new. They can be made by one
  • process E in the presence of an acid-binding agent and optionally in the presence of a diluent.
  • dihalogen-1,3,5-triazine amines of the formula (VII) used as starting compounds in process D are known and / or can be prepared by known processes.
  • the malodinitrile-substituted dialogen-1,3,5-triazines of the formula (VIU) used as starting compounds in process E are new. They can be prepared by using a cyanuric halide of formula (X)
  • the doubly malodi-nitrile-substituted 1,3,5-triazine-alines of formula (VI) used as starting compounds according to process C are new. They can be manufactured by:
  • Rl has the meaning given above
  • Rl has the meaning given above
  • the doubly malodi-nitrile-substituted halogen-1,3,5-triazines of the formula (XI) used as starting compounds according to process H are new. They can be prepared by using a cyanuric halide of formula (X)
  • process K in the presence of an acid-binding agent and optionally in the presence of a diluent
  • the triple malodi nitrile-substituted 1,3,5-triazines of the formula (XII) used as starting compounds according to process J are new. They can be prepared by using a cyanuric halide of formula (X)
  • process LV in the presence of an acid-binding agent and optionally in the presence of a diluent
  • X 1 is -C (CN) 2 -Z, X 2 is -NH-R 1 and X 3 is Cl or F (IV);
  • X 1 and X 2 are -C (CN) 2 -Z and X 3 is -NH-R 1 (VI);
  • X 1 is -C (CN) " Z is t and X 2 and X 3 are Cl or F (Vffl);
  • X 1 and X 2 are -C (CN) 2 -Z and X 3 is Cl or F (XI);
  • X 1 , X 2 and X 3 represent -C (CN) 2 -Z (Xu),
  • R 1 represents alkyl, cycloalkyl, alkoxyalkyl, cyanoalkyl, haloalkyl or phenylalkyl optionally substituted by halogen or alkyl and
  • Z represents a saturated or unsaturated aliphatic radical, phenylalkyl optionally substituted by halogen or phenyl optionally substituted by halogen.
  • the new production processes A to L are also the subject of the present invention. While processes B, E and H are so-called analogy processes, the other processes A, C, D, F, G, I, K and L as such should be inventive; this applies in particular to the two processes C and I, which are characterized by a novel nucleophilic exchange reaction on the triazine ring system (displacement of the malononitrile residue by primary aliphatic amines).
  • the amines of the formulas (V) and (IX) are known.
  • Suitable representatives are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, allyl and benzylamine, also cyclopropylamine, 1,1-dimethylpropin-2-ylamine, 1-phenylethylamine, 1-methyl-1-phenylethylamine, l- (4 ⁇ chlorophenyl) ethylamine, l- (2-chlorophenyl) ethylamine, l- ( 2,4,6-trimethylphenyl) ethylamine, 1-cyano-1-methylethylamine, 2-methoxyethylamine, 3-methoxypropylamine, 4-methoxybutylamine, 2-chloroethylamine, 2,2,2 Trichloroethylamine, 2,2,2-trifluoroethylamine, (
  • Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2,2-dimethylpropyl ( neopentyl), hexyl, heptyl, octyl, allyl, propinyl, benzyl , 4-chlorobenzyl, 2-chlorobenzyl, 1-phenylethyl, 2-phenylethyl, l- (4-chlorophenyl) -ethyl, l- (2-chloro-henyl) -ethyl, phenyl, 2-, 3- and 4- Chlorophenyl.
  • C 1 -C 6 -alkyl radicals are particularly preferred, and the above-mentioned C 1 -C 6 -alkyl radicals are very particularly preferred.
  • reaction temperatures In the following general information regarding the reaction temperatures, molar ratios, diluents, acid binders and working up with regard to processes A to L, in cases where the reaction conditions are practically the same, these are expediently described in the following.
  • reaction temperatures can be varied within a certain range in process A according to the invention. Generally one works between 0 ° C and 200 ° C, preferably between 20 ° C and 150 ° C. With the raw materials of the general In my formula (II), in which shark represents fluorine, the reaction temperatures are generally 30 ° C to 50 ° C lower than those in which shark represents chlorine
  • reaction temperatures in processes B to L can also be varied within a certain range. In general, one works between -50 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.
  • the starting materials of the general formulas (IV), (VD), (VHI), (X) and (XI), which may contain fluorine or chlorine the same applies as for process A.
  • the starting materials and, if appropriate, the acid binders are used in approximately equimolar amounts; however, a small excess (for example 5 to 20 mol%) of the more volatile starting materials, that is to say the 2-substituted malodinitriles of the formula (DI) (in process A) or the amines of the formula (V) (in processes B and C) and optionally the acid binder can be advantageous.
  • the starting materials and the acid binder can be used in equimolar amounts; however, it has been shown that even at relatively mild temperatures (room temperature), in addition to the desired compounds of the formula (IV), the compounds of the formula (VI) which are substituted twice by malodinitrile are also formed. This inevitably has the consequence that the reaction mixture contains the starting materials of the formula (VD) as a third component.
  • the desired compounds of the formula (IV) according to the invention can be e.g.
  • the relative amount formation of the compounds (VDI), (XI) and (XD) is strongly dependent on the type of acid binder.
  • the triple malodinitrile-substituted compound ( XD) in a yield of about 20% of theory, based on the 2-substituted malodinitrile (DI), obtained (see experimental example).
  • the reactions are preferably carried out in the presence of a diluent.
  • a diluent all inert organic solvents are suitable as diluents.
  • these are preferably hydrocarbons, such as benzene, toluene and xylene; chlorinated hydrocarbons, such as chloroform, carbon tetrachloride and chlorobenzene; Ketones such as acetone and ethyl methyl ketone; Nitriles; such as acetonitrile and propionitrile; Ethers such as tetrahydrofuran and dioxane; Amides such as dimethylformamide; Sulfoxides such as dimethyl sulfoxide.
  • processes C and J require acid binders.
  • all customary acid binding agents can be used as acid binders.
  • These preferably include the tertiary amines, such as triethylamine, triethylamine and pyridine, alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide, alkali metal carbonates, such as sodium carbonate and potassium carbonate, and also potassium tert-butylate and sodium hydride.
  • reaction products are worked up and isolated in the customary manner.
  • processes A to E and G to J when water is added to the reaction mixture, optionally after the solvent has been previously distilled off, the reaction products are generally already crystalline or, if they are oily, with a water-immiscible solvent, such as methylene chloride or toluene.
  • the workup can also be carried out non-aqueous, for example by distilling the solvent to remove the reaction ⁇ products (and optionally the starting materials) a fractional vacuum sublimation or an extraction with suitable inert organic solvents, such as cyclohexane or toluene
  • suitable inert organic solvents such as cyclohexane or toluene
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention as otal or selective
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and can be used for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon crops, such as e.g. Cereals and corn, post-emergence.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric fabrics.
  • These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, ayl sulfonates and protein hydrolysates;
  • Possible dispersants are: e.g. Ligin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipi, can be used in the formulations.
  • de such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids such as dichloipicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as, for example, 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxäprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chloropropham, desmedipham, phenmedipham and propham; Chloroacetanilides, such as, for example, alachlor, acetochlor, butachlor, metazachlor, me
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.
  • a solution of 1.76 g (0.022 mol) of 2-methylmalodinitrile in 30 ml of dioxane is mixed with stirring and with exclusion of moisture with 2.46 g (0.022 mol) of potassium tert-butoxide. After stirring for two hours at room temperature, a suspension of 4.3 g (0.02 mol) of 6-chloro-N-ethyl-N'-isopropyl- [1,3,5] triazine-2,4-diamine (atrazine) is added . The mixture is then stirred at 50 ° C for about 40 hours.
  • the reaction temperature was 50 ° C.
  • the reaction temperature was 100 ° C.
  • a solution of 18.5 g (0.1 mol) of cyanuric chloride and 8.0 g (0.1 mol) of 2-methylmalodinitrile in 250 ml of dry acetonitrile is mixed with 13.8 g (0.1 mol) of anhydrous potassium carbonate and stirred vigorously at room temperature for about 3 days in the absence of atmospheric moisture. The mixture is then evaporated to dryness on a rotary evaporator and the residue is subjected to fractional vacuum sublimation (approx. 0.1 mbar).
  • Unreacted cyanuric chloride is initially isolated in the range from 60 to 80 ° C .; in the range around 100 ° C., the 2- (4,6-dichloro- [1,3,5] triazin-2-yl) -2-methyl-malodinitrile of the above structural formula sublimes in needles.
  • the compound can be freed from residual cyanuric chloride by recrystallization from petroleum ether.
  • the compound can be recrystallized from cyclohexane.
  • the 2- [4,6-bis (l, l-dicyano-ethyl) - [1, 3,5] triazin-2-yl] -2-methyl-malodinitrile sublimes in the range between 200 and 250 ° C. Melting point 258 to 259 ° C.
  • Example 17 After stirring for three days at room temperature, the mixture is evaporated to dryness on a rotary evaporator and the residue is subjected to fractional vacuum sublimation as described in Example 17.
  • the temperature range from 200 to 250 ° C. about 2.6 g of 2- [4,6-bis- (1,1-dicyano-ethyl) - [1,3,5] triazin-2-yl] -2 -methyl-malodinitrile of the above structural formula isolated in pure form, identical in all properties to the compound described at the end of Example 17. Yield, based on 2-methyl-malodinitrile: 20.6% of theory.
  • Analpg example 6 was produced:
  • the following compound (A) is used as a comparative substance.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • test plants With the preparation of active ingredient, test plants are sprayed which have a height of 5-15 cm in such a way that the desired amounts of active ingredient are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 2000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Table A-2 Post emergence test / greenhouse

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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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

De nouvelles 1,3,5-triazin-diamines substituées par malodinitrile répondent à la formule (I), dans laquelle R1 et R2 sont identiques ou différents et désignent alkyle, cycloalkyle, alcoxyalkyle, cyanalkyle, halogénure d'alkyle ou phénylalkyle substitué le cas échéant par halogène ou alkyle; et Z désigne un reste aliphatique saturé ou insaturé, phénylalkyle substitué le cas échéant par halogène, ou phényle substitué le cas échéant par halogène. L'invention concerne également plusieurs procédés de préparation de ces composés, des produits intermédiaires utilisés pour les préparer, et leur utilisation comme herbicides.
PCT/EP1994/002790 1993-09-02 1994-08-23 1,3,5-triazin-diamines substituees par malodinitrile a effet herbicide WO1995006642A1 (fr)

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Application Number Priority Date Filing Date Title
AU75366/94A AU7536694A (en) 1993-09-02 1994-08-23 Malodinitril-substituted 1,3,5-triazin-diamines with herbicidal activity

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DE19934329598 DE4329598A1 (de) 1993-09-02 1993-09-02 Malodinitril-substituierte 1,3,5-Triazin-diamine
DEP4329598.3 1993-09-02

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997008156A1 (fr) * 1995-08-24 1997-03-06 Hoechst Schering Agrevo Gmbh 2,4-diamino-1,3,5-triazines, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance de vegetaux

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0073974A2 (fr) * 1981-08-29 1983-03-16 Bayer Ag s-Triazines-4,6-diamino contenant du fluor, procédé et intermédiaires pour leur préparation et leur utilisation comme herbicides
DE3900300A1 (de) * 1989-01-07 1990-07-12 Bayer Ag L-(2-halogen-4-amino-6-(1-methyl-2,2,2- trifluorethyl-amino)-s-triazine), verfahren zu ihrer herstellung und ihre verwendung als herbizide
EP0410590A1 (fr) * 1989-07-27 1991-01-30 AgrEvo UK Limited Herbicides dérivés de pyrimidines
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EP0514551A1 (fr) * 1990-11-30 1992-11-25 Kumiai Chemical Industry Co., Ltd. Derive d'alcanamide, son sel, son procede de production associe et herbicide
WO1994005644A1 (fr) * 1992-09-09 1994-03-17 Schering Agrochemicals Limited Herbicides derives de la pyrimidine

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EP0073974A2 (fr) * 1981-08-29 1983-03-16 Bayer Ag s-Triazines-4,6-diamino contenant du fluor, procédé et intermédiaires pour leur préparation et leur utilisation comme herbicides
DE3900300A1 (de) * 1989-01-07 1990-07-12 Bayer Ag L-(2-halogen-4-amino-6-(1-methyl-2,2,2- trifluorethyl-amino)-s-triazine), verfahren zu ihrer herstellung und ihre verwendung als herbizide
EP0410590A1 (fr) * 1989-07-27 1991-01-30 AgrEvo UK Limited Herbicides dérivés de pyrimidines
EP0422751A2 (fr) * 1989-10-09 1991-04-17 Hoechst Schering AgrEvo GmbH Dérivés d'acide 2-pyrimidinyl et 2-triazinylacétique substitués, procédé pour leur préparation et leur utilisation comme agent herbicide, fongicide et régulateur de croissance des plantes
WO1992001677A1 (fr) * 1990-07-19 1992-02-06 Schering Agrochemicals Limited Herbicides de triazinyle et pyrimidinyle
EP0514551A1 (fr) * 1990-11-30 1992-11-25 Kumiai Chemical Industry Co., Ltd. Derive d'alcanamide, son sel, son procede de production associe et herbicide
WO1992016511A1 (fr) * 1991-03-13 1992-10-01 Schering Agrochemicals Limited Herbicides
WO1994005644A1 (fr) * 1992-09-09 1994-03-17 Schering Agrochemicals Limited Herbicides derives de la pyrimidine

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997008156A1 (fr) * 1995-08-24 1997-03-06 Hoechst Schering Agrevo Gmbh 2,4-diamino-1,3,5-triazines, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance de vegetaux
US6239071B1 (en) 1995-08-24 2001-05-29 Hoecht Schering Agrevo Gmbh 2,4-diamino-1,3,5-triazines, processes for their preparation and their use as herbicides and plant growth regulators

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AU7536694A (en) 1995-03-22

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