Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
  • C07D239/52—Two oxygen atoms
  • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
  • C07D239/60—Three or more oxygen or sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
  • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to novel herbicidally active and plant-growth-regulating pyrimidinyl- and triazinylsalicyl- and -picolinylaldehyde derivatives, to processes for their preparation, to compositions containing them as active substances, and to their use for controlling weeds, mainly selectively in crops of useful plants or for regulating and inhibiting plant growth.
• pyrimidinyl- and triazinylsalicyl- and -picolinylaldehyde derivatives according to the invention are those of the formula I
• W is oxygen or NR 4 ;
• B is nitrogen, methine, or methine which is substituted by fluorine, chlorine, methyl, methoxy, 2-propenyloxy, 2-propynyloxy, difiuoromethoxy or benzyloxy;
• Y is oxygen or sulfur;
• Z is methine or nitrogen
• R 1 is chlorine, methyl, methoxy, ethoxy, difluoromethoxy, methylamino, ethylamino or dimethylamino;
• R 2 is methyl, methoxy or difluoromethoxy
• R 3 is hydrogen, fluorine, chlorine, methyl or methoxy
• R 4 is C ⁇ alkyl, or C- ⁇ alkyl which is substituted by up to 3 fluorine atoms, 1 chlorine atom, 1 group, 1 dimethylcarbamoyl group, 1 carbamoyl group, 1 cyano group, 1 vinyl group, 1 ethynyl group or 1 phenyl group which is unsubstituted or substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy, or is phenyl, or phenyl which is up to trisubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or nitro, orNR 5 R 6 , or OR 7 ;
• R 5 is hydrogen or C ⁇ alkyl
• R 6 is hydrogen, C ⁇ alkyl, phenyl, pyridyl, 1,3-thiazinyl, pyridazinyl, pyrazinyl, pyrimidinyl, or phenyl which is monosubstituted to trisubstituted or pyridyl which is monosubstituted to disubstituted by C ⁇ alkyl, fluorine, chlorine, bromine, trifluoromethyl, methoxy or nitro; or pyridazinyl or pyrazinyl each of which is monosubstituted by methyl, fluorine, chlorine, trifluoromethyl or methoxy; or pyrimidinyl which is monosubstituted to disubstituted by methyl, trifluoromethyl or methoxy; or benzylcarbonyl, pyridylcarbonyl, furylcarbonyl, thiophenylcarbonyl or benzoyl each of which is monosubsti
• R 7 is hydrogen, C j . 6 alkyl or C 2 .
• alkyl and alkenyl radicals can be straight-chain or branched. The same is also true for the, or each, alkyl moiety of alkoxy-, alkylthio-, alkoxycarbonyl- and of further alkyl-containing groups.
• C 1 . 6 alkyl or C j ⁇ alkyl is, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl and the pentyl isomers, and hexyl and the hexyl isomers.
• the alkyl groups which are present as, or in, the substituents preferably have 1 to 4 carbon atoms.
• the C 2 . 6 alkenyl and C 2 . 6 alkynyl radicals which occur in the substituents can be straight-chain or branched.
• Preferred alkenyl radicals are those having a chain length of two to three carbon atoms.
• Examples of C 2 . 6 alkenyl radicals are: vinyl, allyl, methallyl, 1 -methyl vinyl, but-2-en-l-yl, pentenyl or 2-hexenyl. Vinyl and allyl are preferred. Examples of C 2 .
• alkynyl radicals are: vinyl, propargyl, l-methyl-prop-2-yn-l-yl, l-methyl-but-3-yn-2-yl, 2-hexynyl or 4-pentynyl.
• the C 3 . 6 cycloalkylcarbonyl groups which occur in the definitions of the substituent R 6 can be unsubstituted or substituted by halogen, methyl, methylthio or methoxy, and they embrace, for example, cyclopropylcarbonyl, 2-fluorocyclopropylcarbonyl, 2,4-difluorocyclopropylcarbonyl, 2-chlorocyclopropylcarbonyl, 2,3-dichlorocyclo- propylcarbonyl, 2-methylcyclopropylcarbonyl, 2-methylthiocyclopropylcarbonyl, 2,3-dimethylcyclopropylcarbonyI, 2-methoxycyclopropyIcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, 3-methylcyclopentylcarbonyl, 3,4-dimethoxycyclopentylcarbonyl, cyclohexylcarbonyl, 3-fluorocyclohexylcarbon
• Ci ⁇ alkylcarbonyl groups which occur in the definitions of the substituent R 6 can be unsubstituted or substituted by halogen, methyl, methylthio or methoxy, and they embrace, for example, chloromethylcarbonyl, dichloromethylcarbonyl, trifluoromethylcarbonyl, methoxymethylcarbonyl or methylthiomethylcarbonyl.
• Preferred compounds amongst those of the formula I are those in which the substituent R 6 " is hydrogen, C ⁇ a-kyl, phenyl, pyridyl, or phenyl which is monosubstituted to trisubstituted or pyridyl which is monosubstituted to disubstituted by C- ⁇ alkyl, fluorine, chlorine, bromine, trifluoromethyl, methoxy or nitro; or is C ⁇ alkylcarbonyl, trifluoromethylcarbonyl, C 3 .
• R 1 is chlorine, methyl, methoxy, ethoxy or difluoromethoxy
• R 2 is methoxy
• d) Y is oxygen
• e) Z is methine
• f) B is unsubstituted methine or methine which is substituted by methyl, chlorine or methoxy, or is nitrogen, preferably unsubstituted methine
• R 3 is hydrogen
• W is NR 4 , R 4 being tert-butyl, phenyl or phenyl which is substituted by halogen, methyl, trifluoromethyl or methoxy
• R 4 is an NR 5 R 6 group in which R 5 is hydrogen or methyl and R 6 is C- ⁇ alkyl, phenyl, or phenyl which is monosubstituted to disubstituted by halogen,
• R 4 is an NR 5 R 6 group in which R 5 is hydrogen or methyl and R 6 is
• Particularly preferred compounds of the group 1) are those, in which R 5 is hydrogen and R 6 is or phenylaminocarbonyl or phenylaminocarbonyl which is substituted by halogen, methyl or methoxy;
• m) W is NR 4 , R 4 being the OR 7 group and R 7 being C ⁇ alkoxycarbonyl-C ⁇ alkyl;
• n) W is NR 4 ;
• o) Z is methine;
• B is nitrogen or methine which is unsubstituted and R 3 is hydrogen, preferred compounds of the group p) are those in which B is methine which is unsubstituted.
• R 1 and R 2 are methoxy; R 3 is hydrogen; Y is oxygen; Z is methine;
• R 1 is methyl, chlorine, ethoxy or difluoromethoxy
• R 2 is methoxy
• R 3 is hydrogen
• Y is oxygen;
• Z is methine;
• R 1 is methyl, methoxy, ethoxy, methylamino or dimethyla ino
• R 2 is methoxy
• R 3 is hydrogen
• Y is oxygen; Z is nitrogen;
• R 4 is tert-butyl, 4-chlorophenyl, 3-methoxyphenyl, 3-trifluoromethylphenyl, N(CH 3 ) 2 , NHC(CH 3 ) 3 , NH-3-chlorophenyl, NH-4-chIorophenyl, NH-4-methoxyphenyl, NH-3-nitrophenyl, NH-2,3-xylyl, NH-2-(3-CF 3 -pyridyl), NHCOCH 3 , NHCOCH 2 CH 3 , NHCO-cyclopropyl, NHCO-benzyl, NHCO-3-chlorophenyl, NHCO-4-chlorophenyl, NHCO-2,3-dichlorophenyl, NHCO-2-pyridyl, NHCO-3-pyridyl, NHCO-4-pyridyI, NHCO-2-furyl, NHCONHCH 2 CH 3 , NH
• Y is sulfur; Z is methine;
• R 4 is tert-butyl, phenyl, 4-chlorophenyl, 3-methoxyphenyl, 3-trifluoromethylphenyl, N(CH 3 ) 2 , NHC(CH 3 ) 3 , NH-3-chlorophenyl, NH-4-chlorophenyl, NH-4-methoxyphenyl, NH-3-nitrophenyl, NH-2,3-xylyl, NH-2-(3-CF 3 )pyridyl, NHCOCH 3 , NHCOCH 2 CH 3 , NHCO-cyclopropyl, NHCO-benzyl, NHCO-3-chlorophenyl, NHCO-4-chlorophenyl, NHCO-2,3-dichIorophenyl, NHCO-2-pyridyl, NHCO-3-pyridyl, NHCO-4-pyridyl, NHCO-2-furyl, NHCOOCH 2 CH 3
• R 1 and R 2 are methoxy; R 3 is hydrogen;
• Y is oxygen
• B is nitrogen, or methine which is substituted by chlorine, methyl or methoxy
• R 4 is tert-butyl, phenyl, 4-chlorophenyl, 3-methoxyphenyl, 3-trifluoromethylphenyl, N(CH 3 ) 2 , NHC(CH 3 ) 3 , NH-3-chlorophenyl, NH-4-chlorophenyl, NH-4-methoxyphenyl, NH-3-nitrophenyl, NH-2,3-xylyl, NH-2-(3-F-5-Cl)pyridyl, NH-2-(3-CF 3 )pyridyl, NHCOCH 2 CH 3 , NHCO-cyclopropyl, NHCO-benzyl, NHCO-3-chlorophenyl, NHCO-4-chlorophenyl, NHCO-2,3-dichlorophenyl, NHCO-2-pyridyl, NHCO-3
• R 1 and R 2 are methoxy; R 3 is hydrogen;
• Y is oxygen;
• Z is methine;
• B is nitrogen, or methine which is substituted by chlorine, methyl or methoxy;
• W is NOR 7 and
• R 1 is methyl, chlorine, methoxy, ethoxy or difluoromethoxy
• R 2 is methoxy
• R 3 is hydrogen
• Y is oxygen; Z is methine; B is methine;
• W is NOR 7 ;
• R 7 is CH(CH 3 )COOCH 3 , CH(CH 2 CH 3 )COOCH 3 , CH(CH 3 )COOCH 2 CH 3 ,
• CH 2 COOCH 2 CH CH 2 , CH 2 COSCH 2 CH 3 or CH(CH 3 )COSCH 2 CH 3 .
• a group of compounds of the formula I which excels particularly because of its good biological action is that in which R 1 is methyl, methoxy, ethoxy, methylamino or dimethylamino; R 2 is methoxy; R 3 is hydrogen;
• Y is oxygen; Z is nitrogen;
• B is methine or nitrogen
• W is NOR 7 ;
• R 7 is hydrogen, methyl, ethyl, propyl, i-propyl, n-butyl, i-butyl, s-butyl,
• R 1 , R 2 , R 3 , Z, Y and B are as defined under formula I, with an amine, hydrazine, hvdrazide, carbazate, semicarbazide or thiosemicarbazide or oxime of the formula III in which R 4 is as defined under formula I, if desired in the presence of a water-binding agent and an inert diluent.
• Compounds of the formula I can also be prepared by reacting a pyrimidine of the formula IV in which R 1 , R 2 and Z are as defined under formula I and L is a leaving group such as fluorine, chlorine, bromine, C ⁇ alkylsulfonyl (for example methylsulfonyl or ethylsulfonyl), benzylsulfonyl, S-C j ⁇ alkylsulfonyl-lH-l ⁇ -triazol-l-yl (for example 3-methylsulfonyl-lH-l,2,4-triazol-l-yl), with an imine, hydrazone, hydrazide, carbazate, semicarbazide, thiosemicarbazide or oxime compound of the general formula V in which R 3 , R 4 , B and Y are as defined under formula I, in the presence of an acid-binding agent, for example n-butyllithium, sodium
• the process is advantageously carried out at 0°C to the boiling point of the solvent used, preferably between room temperature and about 100°C.
• R 6 in the definition NR 5 R 6 is C ⁇ alkylcarbonyl, trifluoromethylcarbonyl, C 3 . 6 cycloalkylcarbonyl, benzylcarbonyl, 2-, 3- or 4-pyridinyl, 2- or 3-furyl or thiophenylcarbonyl, or benzoyl which is monosubstituted to disubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or nitro; or C j .
• compounds of the formula V can be prepared by oxidising a compound of the formula VIII (cf. for example, Tetr. 3, 49-55 (1958) and J. Amer. Chem. Soc. 76, 648-652 (1954)) in which Y is as defined under formula I, by known methods using a suitable oxidising agent [ox], for example manganese dioxide. vi ⁇ '
• the compounds of the formula I have herbicidal properties and are suitable for controlling weeds, including grass weeds, for example, inter alia, Agropyron repens, Alopecurus myosuroides, Avena fatua, Bromus inermis, Echinochloa crus-galli, Poa annua, Sorghum halepense, Abutilon theophrasti, Amaranthus retroflexus, Cassia obtusifolia, Chenopodium album, Galium aparine, Matricaria chamomilla, Sinapis arvensis and Stellaria media in a range of crops of useful plants, for example, inter alia, rice crops, in particular paddy rice, wheat, maize, soya, oilseed rape, sunflowers and cotton. Moreover, the compounds are both pre-emergence and post-emergence herbicides. In some compounds of the formula I, a good selectivity was noticed, for example in the control of weeds in wheat,
• the compounds of the formula I have plant-growth-regulating properties and are suitable as active substances for positively influencing the growth of useful plants.
• This effect can lead to a desired growth inhibition in crop plants and also inhibit the germination of weeds sufficiently to eliminate them as competitors of the crop plants. From an ecological point of view, this is advantageous and hence extremely desirable.
• Aspects which should be mentioned in particular are the protection of the soil surface from drying out and/or erosion and the reduction of the bulk of weed seeds in the soil (combined with prevention of flowering and further seed production). This effect may therefore be preferred to the complete prevention of weed formation, which may, however, be limited to a particular period.
• a concentration of 1 g to 3 kg of the compound of the formula I per ha is usually sufficient for achieving the desired herbicidal effect.
• the range from 10 to 100 g/ha is particularly favourable when carrying out a pre-e ergence treatment, and the range from 100 to 1000 g/ha is particularly favourable when carrying out a post-emergence treatment.
• the weedkillers and plant-growth regulators according to the invention comprise an effective amount of at least one compound of the formula I and, as a rule, also formulation auxiliaries.
• they each comprise at least one formulation auxiliary from each of the following groups:
• the pesticidal formulations comprise, as a rule, besides the active substances of the formula 1 1 to 99 % of a formulation auxiliary from the group comprising
• the compounds of the formula I i.e. the herbicidal active substances
• the customary formulations such as dusts, powders, granules, solutions, emulsions, suspensions, emulsifiable concentrates, pastes and the like.
• the compounds of the formula I are generally water-insoluble and can be formulated by methods customary in the case of water-insoluble compounds, using the known formulation auxiliaries.
• the compositions can be prepared in a manner known per se, for example by mixing the particular active substance with solid carriers, by dissolving or suspending in suitable solvents or dispersants, with or without the use of surfactants as wetting agents or emulsifiers and/or dispersants, or by diluting prefabricated emulsifiable concentrates with solvents or dispersants.
• - natural minerals such as chalk, dolomite, limestone, clays and silica and its salts, for example kieselguhr, kaolin, bentonite, talc, attapulgite or montmorillonite
• - synthetic minerals such as highly-disperse silica, alumina or silicates
• organic substances such as cellulose, starch, urea or artificial resins
• - fertilisers such as phosphates or nitrates.
• Such carriers can be, for example, in the form of powders or granules.
• aromatic substances such as benzene, toluene, xylene and alkylnaphthalenes
• chlorinated aromatic substances and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylenes or methylene chloride;
• aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions
• ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
• solvents or dispersants such as dimethylformarnide, N-methylpyrrolidone or dimethyl sulfoxide (such solvents preferably having flash points of at least 30°C and boiling points of at least 50°C), or water.
• Suitable solvents or dispersants are also so-called liquefied gaseous, extenders or carriers, which are products which are gaseous at room temperature and under atmospheric pressure.
• liquefied gaseous, extenders or carriers which are products which are gaseous at room temperature and under atmospheric pressure.
• aerosol propellants such as halohydrocarbons, for example dichlorodifluoromethane.
• the weedkiller according to the invention is in the form of a pressurised gas pack, it is advantageous to employ a solvent in addition to the propellant.
• the surfactants can be non-ionic compounds, such as:
• the surfactants can also be anionic compounds, such as:
• fatty sulfate esters for example dodecyl sodium sulfate, octadecyl sodium sulfate or cetyl sodium sulfate;
• alkylsulfonates arylsulfonates or fatty-aromatic sulfonates, such as alkylbenzenesulfonates, for example calcium dodecylbenzenesulfonate or butylnaphthalenesulfonates; or
• - more complex fatty sulfonates for example the amide condensation products of Isure and N-methyltaurine, or the sodium sulfonate of dioctyl succinate.
• the surfactants can be cationic compounds, such as alkyldimethylbenzylammonium chlorides, dialkyldimethylammonium chlorides, alkylmethylammonium chlorides or ethoxylated ammonium chlorides.
• lignin mainly suitable as dispersants (without surfactant action): lignin, sodium salts and ammonium salts of ligninsulfonic acids, sodium salts of maleic anhydride/diisobutylene copolymers, sodium salts and ammonium salts of sulfonated polycondensation products of naphthalene and formaldehyde, or sulfite waste liquors.
• Dispersants which are particularly suitable as thickeners or anti-settling agents which cm be employed are, for example, methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, polyvinyl alcohol, alginates, caseinates or blood albumin.
• antioxidants for example gallic esters or butylatedhydroxy toluene
• UV absorbers for example substituted benzophenones, diphenyl- ⁇ -cyano acrylic acid esters or cinnamic esters; or
• - deactivators for example salts of ethylenediaminotetraacetic acid, or polyglycols.
• the weedkillers and plant-growth regulators according to the invention can also contain other active substances, for example insecticides, acaricides, nematicides, molluscicides, bactericides, fungicides, herbicides, plant-growth-regulating substances, fertilisers and trace-element sources.
• active substances for example insecticides, acaricides, nematicides, molluscicides, bactericides, fungicides, herbicides, plant-growth-regulating substances, fertilisers and trace-element sources.
• the weedkillers according to the invention comprise between 0.001 and 95 %, preferably between 0.5 and 75 %, by weight of one or more of the compounds of the formula I as active substance.
• they can be in a form which is suitable for storage and transport.
• the active substance concentration is usually in a higher range, preferably between 1 and 50 % by weight, in particular between 5 and 30 % by weight.
• these formulations can then be diluted, for example with identical or different inert substances, down to the active substance concentration which is suitable for use in practice, viz. preferably about 0.001 to 10 % by weight, in particular about 0.005 to 5 % by weight.
• the active substance concentrations can also be lower or higher.
• the weedkiller according to the invention can be prepared in a manner known per se.
• the active substance i.e. at least one compound of the formula I
• a solid carrier for example by simultaneous grinding.
• the solid carrier can be impregnated with a solution or suspension of the active substance, and the solvent or dispersant can then be removed by evaporation, heating or filtering off under reduced pressure.
• surfactants or dispersants it is possible to render such agents, which are in the form of powders, readily wettable with water, so that they can be converted into aqueous suspensions which are suitable, for example, as sprays.
• the active substance can be mixed with the surfactant and a solid carrier to give a wettable powder which is dispersible in water, or it can be mixed with a solid, pregranulated carrier to give a product in the form of granules.
• the active substance can be dissolved in a solvent which is not miscible with water, for example a high-boiling hydrocarbon.
• This solvent expediently contains a dissolved emulsifier, so that the solution is self-emulsifying when added to water.
• the active substance can be mixed with an emulsifier, and the mixture can then be diluted with water to the desired concentration.
• the active substance can be dissolved in a solvent, and the solution can then be mixed with an emulsifier.
• Such a mixture can also be diluted with water to the desired concentration. In this manner, emulsifiable concentrates or ready-for-use emulsions are obtained.
• the weedkillers described can be used according to the invention in customary application methods, such as spraying, atomising, dusting, pouring or scattering.
• Example 2 4,6-Dimethoxy-2-[[ ⁇ -[(E and/or Z)-phenylimino]-o-tolyl]oxy]pyrimidine (Compound No. 1.007) can be prepared as follows: 2.60 g of 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzaldehyde and 1.05 g of aniline in 25 ml of ethanol and in the presence of 3 drops of acetic acid are maintained at reflux temperature for 45 minutes. The reaction mixture is cooled to -5°C, and the product which has precipitated is filtered off and washed with ice-cold ethanol.
• Example 3 4,6-Dimethoxy-2-[[ ⁇ -[(E and/or Z)-phenylimino]-o-tolyl]oxy]pyrimidine (Compound No. 1.007) can also be prepared as follows:
• Example 4 2-fT ⁇ -r(E and/or Z)-tert-butylimino]-o-tolynoxy]-4,6-dimethoxypvrimidine (Compound No. 1.008) can be prepared as follows:
• Example 5 o-[(4,6-Dimethoxy-2-pyrimidinyl)oxy]benzaldehyde (E and/or Z)-phenylhydrazone (Compound No. 1.054) can be prepared as follows:
• Example 6 N'-(E and/or Z)-o-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylidene]- propionohydrazide (Compound No. 1.055) can be prepared as follows:
• Example 7 2-[(4,6-Dimethoxy-2-pyrimidinyl)oxy] benzaldehyde o-ethoxycarbonylmethyl oxime (Compound No. 4.003) can be prepared as follows:
• Example 8 3-[(4,6-Dimethoxy-2-pyrimidinyl)oxy)pyridine-2-carboxaldehyde oxime (Compound No. 4.004) can be prepared as follows: A methanolic solution of 1.0 g of sodium acetate and 0.7 g of hydroxylamine hydrochloride is briefly heated to reflux temperature. 1.8 g of 3-[(4,6-dimethoxy-2-pyrimidinyl)oxy]pyridine-2-carboxaldehyde (Example 1) are introduced after 1 minute. The reaction mixture is kept at reflux temperature for a further 5 minutes, and such an amount of water is then added until a clear solution is obtained. On cooling, 3-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-pyridine-2-carboxaldehyde oxime (Compound No.4.004) precipitates as white crystals; melting point 169-171°C.
• Example Fl To prepare a 25 % wettable powder, the components listed below are mixed with ea other:
• the liquid or molten active substance is applied to the silica which has been introduced into grinding apparatus.
• the other components are subsequently admixed.
• the mixture is ground finel using a pin mill or a comparable grinding apparatus.
• the resulting wettable powder When stirred into water, the resulting wettable powder gives a fine suspension which is suitable a a ready-for-use spray mixture.
• Active substances which are particularly suitable for this formulation are compounds of the formula I which are liquid or which have a low melting point, i.e. up to about +100°C.
• Example F2 Compounds of the formula I which have a high melting point, i.e. above about +100°C, can preferably be used as active substances in concentrated wettable powders, for exampl as follows:
• the components are mixed with each other and ground finely using a pin mill or a comparable grinding device, in particular a jet mill.
• the resulting wettable powder When stirred into water, the resulting wettable powder gives a fine suspension of any desired concentration which is suitable as a ready-for-use spray mixture.
• Example F3 A wettable powder based on the composition of Example F3 can also be converted into dispersible granules.
• the ground powder is sprayed with an aqueous solution of the binder in a suitable granulation apparatus (for example granulation plate, mixing drum, high-speed stirrer or fluidised-bed granulator) until agglomerations have formed.
• a suitable granulation apparatus for example granulation plate, mixing drum, high-speed stirrer or fluidised-bed granulator
• the water which has been added is removed again in a drying process.
• the granules of the desired size are collected by sieving.
• Example F4 The compounds of the formula I have limited solubility in the customary organic solvents. Accordingly, emulsifiable concentrates of relatively low concentration are possible; fo example:
• the active substance and the emulsifier are introduced into the solvent, with stirring.
• the mixtur is stirred until a homogeneous solution has formed.
• the resulting emulsifiable concentrate can be emulsified in water, which gives a ready-for-use spray mixture of the desired concentration.
• Example F5 Compounds of the formula I having a melting point higher than about +60°C can a be formulated as so-called suspension concentrates ("flowables"); for example:
• the formulation auxiliaries are dissolved in water.
• the pre-ground active substance is dispersed the solution, with stirring.
• the resulting coarse suspension is now subjected to wet grinding (for example in a colloid mill or a stirred ball mill). If desired, small amounts of further additives are now possible, such as antifoam agents, anti-settling agents and biocides.
• the resulting "flowable" can be diluted with water as desired, giving a ready-for-use spr mixture of the desired concentration.
• the soil surface is treated with an aqueous spray mixtur corresponding to a rate of application of 3 kg of active substance/hectare.
• test substances are preferably formulated as emulsifiable concentrate (EC) and diluted with water to the desired concentration immediately before application.
• Insoluble substances are formulated as a wettable powder (WP), using kaolin as the inert carrier. This wettable powder is suspended in water immediately before application.
• WP wettable powder
• the dosage rates in g of active ingredient ha relate to the soil surface in the containers, unless otherwise indicated.
• the spray volume is 5001 ha.
• the seeds of the plants are sown in plastic plant pots of various sizes containing heat-sterilised (steamed) soil (terrestial soil 2.6 % peat, 20 % clay, 30 % silt, 47 % sand).
• the plants are kept in the greenhouse at an average temperature (17 - 25°C in winter, 18 - 35°C in summer) (atmospheric humidity 30 - 90 ).
• the length of the photoperiod is 13 to 16 hours/day; if necessary, artificial light is added (15000 to 18000 lux). Artificial illumination is also activated automatically when the daylight intensity is insufficient.
• Table B 1 Examples of the good herbicidal action of the compounds of the formula I which are described in the tables of the present application are listed in Table B 1 : Table Bl: Pre-emergence herbicidal action:
• Example B2 Post-emergence herbicidal action (contact herbicide) After emergence (in the 4- to 6-Ieaf stage), a number of weeds, both monocotyledon and dicotyledon, were treated with an aqueous dispersion of active substance at a dosage rate of 3 kg of active ingredient per hectare.
• test substances are preferably formulated as an emulsifiable concentrate (EC), and diluted with water to the desired concentration immediately before application.
• Insoluble substances are formulated as a wettable powder (WP), using kaolin as the inert carrier. This wettable powder is suspended in water immediately before application.
• WP wettable powder
• dosage rates in g of active ingredient/ha are based on the soil surface in the containers.
• the spray volume is 5001/ha.
• the seeds of the plants are sown in plastic plant pots of various sizes containing heat-sterilised (steamed) soil ("Optima" soil 80 % peat, 20 % loess).
• the plants are kept in the greenhouse at an average temperature (17 - 25°C in winter, 18 - 35°C in summer) (atmospheric humidity 30 - 90 %).
• the length of the photoperiod is 13 to 16 hours/day; if necessary, artificial light is added (15000 to 18000 lux). Artificial illumination is also activated automatically when the daylight intensity is insufficient.
• Table B2 Post-emergence herbicidal action:
• SORG denotes Sorghum halepense Johnsongrass
• ECHI denotes Echinochloa crus-galli barnyard grass
• AVEN denotes Avena fatua Wild oat
• ALOP denotes Alopecurus myosuroides
• Blackgrass CHEN denotes Chenopodium album Lambs quarters
• STEL denotes Stellaria media
• Chickweed ABUT denotes Abutilon theophrasti Velvetleaf
• Example B3 Herbicidal action for paddy rice
• the seeds of the plants are sown in plastic beakers or boxes of various sizes, sealed at the bottom end and containing fertilised soil.
• the soil is heat-sterilised (steamed) and contains about 80 % (w/v) loam and 20 % peat and 0.05 % Nutricote (16/10/10) and 0.05 % "Plantamaag" as fertiliser.
• the plants are kept in a special greenhouse cabin at a high temperature (20-35°C) and high atmospheric humidity (60-80 %), the latter being kept constant by means of a sprinkler system.
• the length of the photoperiod is 13 to 16 hours/day; if necessary, artificial light (15000 to 18000 lux) is added. Artificial illumination is also activated automatically when the daylight intensity is insufficient.
• test substances are preferably formulated as emulsifiable concentrates (EC) and diluted to the desired concentration with water immediately before application.
• Insoluble substances are formulated as a wettable powder (WP), using kaolin as the inert carrier. This wettable powder is suspended in water immediately before application.
• WP wettable powder
• the dosage rates in g of active ingredient/ha are relative to the soil surface in the containers, unless otherwise indicated.
• the spray volume is 5001 ha.
• the compounds of the formula I have a selective herbicidal action against the weeds.

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• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Plant Pathology (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Pyridine Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)

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• 1991
  • 1991-02-05 GB GB919102423A patent/GB9102423D0/en active Pending
• 1992
  • 1992-01-04 AU AU11538/92A patent/AU1153892A/en not_active Abandoned
  • 1992-01-04 WO PCT/EP1992/000010 patent/WO1992013846A1/en active Application Filing
  • 1992-01-16 TW TW081100272A patent/TW222624B/zh active
  • 1992-02-03 NZ NZ241501A patent/NZ241501A/en unknown
  • 1992-02-03 MX MX9200468A patent/MX9200468A/es unknown
  • 1992-02-04 ZA ZA92786A patent/ZA92786B/xx unknown

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