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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/34—One oxygen atom
  • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/38—One sulfur atom
  • C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical

Definitions

• the invention relates to new substituted pyrimidine (thi) ones, a process for their preparation and their use as herbicides.
• Q oxygen or sulfur
• R 1 represents hydrogen, cyano, nitro, halogen, alkyl or haloalkyl
• R 2 represents cyano or thiocarbamoyl
• R 3 represents the grouping below, -A'-A 2 -A 3 wherein
• a 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxyl, amino, alkyl, alkoxy, aryl, Alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, arylcarbonyl or arylsulfonyl, or
• a 1 furthermore stands for optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or arendiyl,
• a 4 represents hydrogen, alkyl, aryl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl,
• a 2 furthermore stands for optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or arendiyl, and
• R 4 represents hydrogen, halogen, alkyl or haloalkyl
• R 5 represents alkyl or haloalkyl or together with R 4 represents alkanediyl.
• R 1 , R 2 and R 3 have the meanings given above, and
• Q, R 4 and R 5 have the meanings given above, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent and optionally on the compounds of the formula (I) thus obtained, the groups denoted Q, R 1 , R 2 , R 3 , R 4 and R 5 in the usual manner subject to chemical changes within the framework of the above radical definition.
• the new substituted pyrimidine (thi) ones of the general formula (I) are notable for strong and selective herbicidal activity.
• the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino - are each straight-chain or branched.
• Halogen generally represents fluorine, chlorine, bromine or iodine, preferably
• the invention preferably relates to compounds of the formula (I) in which
• R 1 represents hydrogen, cyano, nitro, fluorine, chlorine, bromine or alkyl which has 1 to 4 carbon atoms and is optionally substituted by fluorine and / or chlorine,
• R 2 represents cyano or thiocarbamoyl
• R 3 represents the grouping below
• a 1 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -
• a 4 represent hydrogen, hydroxy, amino, C r C 4 alkyl , C r C 4 alkoxy, phenyl, C r C 4 alkylcarbonyl, C j -C 4 alkoxycarbonyl, C j -C 4 alkylsulfonyl, phenylcarbonyl or phenylsulfonyl, or
• a 1 furthermore represents in each case optionally substituted by fluorine, chlorine or bromine-substituted C j -C 6 -alkanediyl, C 2 -C 6 -alkenediyl, C 2 -C 6 -Azaalken- diyl, C 2 -C. 6 Alkindiyl, C 3 -C 6 -cycloalkanediyl, C 3 -C 6 -cycloalkenediyl or phenylene,
• a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, where A 4 represents hydrogen, hydroxy, C 1 -C 4 alkyl, C r C 4 alkoxy, phenyl, C, -C 4 alkyl sulfonyl or phenyl sulfonyl,
• a 2 further for C ] -C 6 -alkanediyl, C 2 -C 6 -alkenediyl, C 2 -C 6 -azaalkenediyl, C 2 -C 6 each optionally substituted by fluorine, chlorine or bromine.
• a 3 further for each optionally substituted by halogen
• a 3 furthermore represents in each case optionally substituted by halogen, cyano, carboxy, C j -C 4 alkyl and / or C] -C 4 -alkoxy-carbonyl substitu ⁇ Neills cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkyl, alkoxy, Cycloalkylidenamino, cycloalkyloxycarbonyl or cyclo - Alkylalkoxy carbonyl with 3 to 6 carbon atoms in each
• a 3 further for each optionally by nitro, cyano, carboxy, halogen C r C 4 alkyl, C r C 4 haloalkyl, C r C 4 alkyloxy, C r C 4 -
• R 4 represents hydrogen, fluorine, chlorine or bromine, or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine, and
• R 5 represents optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms or together with R 4 represents C 3 -C 4 alkanediyl.
• the invention relates in particular to compounds of the formula (I) in which
• R 1 represents hydrogen, fluorine or chlorine
• R 2 represents cyano or thiocarbamoyl
• R 3 represents the grouping below
• a 1 stands for a single bond, for oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 stands for hydrogen, hydroxy, methyl, ethyl, n- or i Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, or
• a 1 furthermore for methylene, ethane-l, l-diyl, ethane-l, 2-diyl, propane-1,1-diyl, propane-l, 2-diyl, propane-l, 3-diyl, ethene-l, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
• a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO 2 -, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen, hydroxy, methyl, ethyl, n- or i Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl, or
• a 2 furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
• a 3 furthermore for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylcarbonyl, each optionally substituted by fluorine or chlorine or butynyloxycarbonyl,
• a 3 furthermore for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl Cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexylidenamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or
• a 3 further for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted
• R 4 represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine, and
• R 5 represents in each case optionally substituted by fluorine and / or chlorine methyl or ethyl.
• the formula (IT) provides a general definition of the haloarenes to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I).
• R 1 , R 2 and R 3 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 1 , R 2 and R 3 have been given;
• X preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine.
• the starting materials of the formula (II) are known and / or can be prepared by known processes (cf. EP-A 431373, EP-A 441004, EP-A 597360).
• Formula (HI) provides a general definition of the pyrimidine (thi) ones to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I).
• Q, R 4 and R 5 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Q, R 4 and R 5 have been given.
• the starting materials of the formula (DI) are known and / or can be prepared by known processes (cf. EP-A 357201, EP-A 395977, preparation examples).
• the process according to the invention is preferably carried out in the presence of a suitable acid acceptor.
• a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, lithium, sodium, potassium or calcium hydride, lithium, sodium or Potassium amide, sodium or potassium methylate, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropylate, sodium or potassium tert-butoxide, sodium or potassium hydroxide, ammonium hydroxide, sodium -, Potassium or calcium acetate, ammonium acetate, sodium, potassium or calcium carbonate, ammonium carbonate, sodium or potassium hydrogen carbonate, and basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropyl amine
• organic solvents are suitable as diluents for carrying out the process according to the invention. This includes in particular - 11
• reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably at temperatures between -10 ° C and + 120 ° C, especially at temperatures between 0 ° C and 100 ° C.
• the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
• the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
• the reactions are generally carried out in a suitable diluent and the reaction mixture is stirred for several hours at the temperature required in each case. Working up in the method according to the invention is carried out in each case by customary methods (cf. the production examples).
• 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 understood to mean all plants that are in places grow up where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
• 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, for example on industrial and rail tracks and on paths and squares with and without tree cover.
• the compounds for weed control in permanent crops for example 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 pastures and for selective weed control in annual crops.
• the compounds of formula (I) according to the invention are particularly suitable for the selective control of dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
• 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 polymers Fabrics.
• formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• extenders that is to say liquid solvents and / or solid carriers
• surface-active agents that is to say 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.
• solid carriers for example 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
• Solid carrier materials for granules are: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks;
• Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, ary
• Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• 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 be used as such or in their formulations, also in a mixture with known herbicides, for weed control, 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 dichloropicolinic 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, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides, such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilach
• 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 5 g and 5 kg of active ingredient per hectare of soil, preferably between 10 g and 2 kg per ha.
• 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.
• Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours.
• the amount of water per unit area is expediently kept constant.
• the concentration of active substance in the preparation is irrelevant; the decisive factor is only the amount of active substance applied per unit area.
• the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
• the compound according to Preparation Example 2 shows very good compatibility with crop plants, such as, for example, when 15 g ha is applied.
• Wheat and soy (0%), as well as strong action against weeds (Abutilon 90%), Amaranthus (80%), Ambrosia (100%), Galinsoga (100%), Solanum (80%) and Viola (80%).

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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)

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• 1994
  • 1994-09-02 DE DE4431218A patent/DE4431218A1/de not_active Withdrawn
• 1995
  • 1995-08-21 KR KR1019970701289A patent/KR100389528B1/ko not_active IP Right Cessation
  • 1995-08-21 JP JP8509158A patent/JPH10505073A/ja not_active Ceased
  • 1995-08-21 BR BR9508778A patent/BR9508778A/pt not_active Application Discontinuation
  • 1995-08-21 CN CN95194892A patent/CN1121392C/zh not_active Expired - Fee Related
  • 1995-08-21 US US08/793,397 patent/US5877121A/en not_active Expired - Fee Related
  • 1995-08-21 MX MX9701569A patent/MX9701569A/es unknown
  • 1995-08-21 EP EP95929895A patent/EP0804424A1/de not_active Withdrawn
  • 1995-08-21 AU AU33472/95A patent/AU3347295A/en not_active Abandoned
  • 1995-08-21 WO PCT/EP1995/003314 patent/WO1996007647A1/de not_active Application Discontinuation

Non-Patent Citations (1)

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