Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
  • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D257/04—Five-membered rings
• • 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<
  • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

• the present invention relates to novel tetrazolinone derivatives, to a process for their preparation and to their use as herbicides.
• R represents a group
• R 3 and R 4 each independently represent a hydrogen atom, C,. 6 alkyl, C,. 6 haloalkyl,
• R 5 represents optionally substituted phenyl, optionally substituted C 7.12 aralkyl, optionally substituted phenoxy-C alkyl or optionally substituted phenylthio- C
• R 1 and R 2 each independently represent C,. I0 alkyl, C,. 6 haloalkyl, C 3 . 8 cycloalkyl,
• R 1 and R 2 together with the nitrogen atom to which they are bonded, form a 5- or 6- membered heterocyclic group, which may be optionally condensed with cyclohexane or benzene or may be optionally substituted by C alkyl or halogen,
• R represents non-substituted C 7 . 9 aralkyl or substituted benzyl
• R 1 represents C,. 6 alkyl, C,. 6 haloalkyl, C 3 . 8 cycloalkyl, C 2 . 6 alkenyl, C 2 . 6 alkinyl, optionally substituted C 7 . 9 aralkyl or optionally substituted phenyl (substituents to these groups being 1-5 groups selected from the group consisting of halogen, C, .6 alkyl, C,. 6 haloalkyl, C,. 6 alkoxy, C,. 6 haloalkoxy, C,. 6 alkylthio,
• R 2 represents C 7 . 10 alkyl, C,. 6 haloalkyl, C 3 or C 7 . 8 cycloalkyl, C 7.10 alkenyl or C 2.6 alkinyl,
• R 1 and R 2 together with the nitrogen atom to which they are bonded, form a 5- or 6- membered heterocyclic group, which are condensed with cyclohexane or ben- zene and may be optionally substituted by C M alkyl or halogen.
• R 1 and R 2 are defined as mentioned above, and M represents a commonly known leaving group such as halogen (e.g. chloro, bromo or iodo), sulfonate (e.g. triflate, mesylate, toluenesulfonate) or alkoxy etc., with chloro, bromo being particularly preferred, in the presence of inert solvents, and if appropriate, in the presence of an acid binding agent.
• halogen e.g. chloro, bromo or iodo
• sulfonate e.g. triflate, mesylate, toluenesulfonate
• alkoxy etc. e.g. triflate, mesylate, toluenesulfonate
• chloro, bromo being particularly preferred, in the presence of inert solvents, and if appropriate, in the presence of an acid binding agent.
• the compounds of the formula (I), according to the present invention have strong herbicidal activities and especially exhibit an excellent herbicidal action combined with a good compatibility with the crops. In this regard they constitute an improvement with regard to the known compounds described in the aforementioned EP-A- 146 279 which are similar to the compounds of the formula (I). Therefore, the compounds of the present invention posses a significant value as selective herbicides.
• Halogen in "halogen”, “haloalkyl”, “haloalkoxy” and “haloalkylthio” represents fluoro, chloro, bromo or iodo, and preferably is fluoro, chloro or bromo.
• Alkyl may be straight chain or branched chain and there may be mentioned, for example, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n- or iso-pentyl, tert-amyl, pentan-3-yl, neopentyl, n-hexyl.
• Alkoxy may be straight chain or branched chain and there may be mentioned, for example, methoxy, ethoxy, propoxy, iso-propoxy, n-, iso-, sec- or tert-butoxy, n- pentyloxy, n-hexyloxy.
• Alkylthio may be straight chain or branched chain and there may be mentioned, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio.
• Alkylsulfinyl may be straight chain or branched chain and there may be mentioned, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butyl- sulfmyl.
• Alkylsulfonyl may be straight chain or branched chain and there may be mentioned, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfo- nyl, n-butylsulfonyl.
• Cycloalkyl includes, for example, cyclopropyl, cyclopentyl, cyclohexyl, cyclo- heptyl and cyclooctyl.
• alkenyl there may be mentioned, for example, allyl, 1-methyl-allyl, 1,1-dimeth- ylallyl.
• alkinyl there may be mentioned, for example, propargyl, 1-methyl-propargyl, 1 , 1 -dimethylpropargyl.
• aralkyl there may be mentioned, for example, benzyl, phenethyl, 1-phenylethyl,
• 3-phenylpropyl 1 -methyl-2-phenylethyl, 2-methyl-2-phenylethyl, ⁇ , ⁇ -dimethyl- benzyl, l-methyl-3-phenylpropyl, ⁇ -propylbenzyl, -isopropylbenzyl, l-ethyl-2- phenylethyl, ,-butylbenzyl, l-ethyl-3-phenylpropyl.
• Haloalkyl may be straight chain or branched chain and there may be mentioned, for example, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromo- ethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2,2-pentafluoroethyl, 2,2,3,3,3-pentafluoropropyl, 3-chloropropyl, 1 ,3-difluoropropan-2-yl, 1,1,1 -trifluoro- propan-2-yl, 2,2,3,3,4,4,4-heptafluorobutyl, 3-bromopropyl.
• Haloalkyl part in "haloalkoxy" and “haloalkylthio" may be as defined in the above- mentioned “haloalkyl”.
• alkoxy carbonyl there may be mentioned, for example, methoxycarbonyl, eth- oxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl.
• "5- or 6-membered heterocyclic group” may be optionally condensed with cyclohexane or benzene and there may be mentioned, for example, pyrrol- 1-yl, pyrrolidin- 1-yl, piperidin-1-yl, indol-1-yl, indolin-1-yl, octahydroindol-1-yl, 1,2-dihydro- quinolin-1-yl, 1, 2,3, 4-tetrahydroquinolin- 1-yl, decahydroquinolin-1-yl.
• heterocyclic groups may be optionally substituted by C alkyl such as methyl, ethyl, propyl, isopropyl, n-, sec-, iso- or tert-butyl etc., or halogen such as fluoro, chloro etc. and in case that a plurality of substituents exist, they may be identical or different each other.
• C alkyl such as methyl, ethyl, propyl, isopropyl, n-, sec-, iso- or tert-butyl etc.
• halogen such as fluoro, chloro etc.
• R represents a group
• R 3 and R 4 each independently represent a hydrogen atom, C, remedy 5 alkyl, C,. 5 haloalkyl,
• R 5 represents optionally substituted phenyl, optionally substituted C 7 . 10 aralkyl, optionally substituted phenoxy-C,. 3 alkyl or optionally substituted phenylthio- C, .3 alkyl (substituents to these groups being 1 to 4 groups selected from the group consisting of halogen, C,. 5 alkyl, C,. 3 haloalkyl, C,. 5 alkoxy, C,. 5 haloalkoxy, C,. 5 alkylthio, C,. 5 alkylsulfinyl, C,. 5 alkylsulphonyl, C, .5 haloalkylthio, phenyl, phenoxy, C,. 3 alkoxycarbonyl, nitro and cyano),
• R 1 and R 2 each independently represent C,. 5 alkyl, C,_ 5 haloalkyl, C 3.7 cycloalkyl, C 2.5 alkenyl, C 2 . 5 alkinyl, optionally substituted C 7.9 aralkyl or optionally substituted phenyl (substituents to these groups being 1 to 4 groups selected from the group consisting of halogen, C,. 5 alkyl, C,. 5 haloalkyl, C,. 5 alkoxy, C, .5 haloalkoxy, C, profession 5 alkylthio, C,_ 5 haloalkylthio, phenyl, phenoxy and nitro), or
• R 1 and R 2 together with the nitrogen atom to which they are bonded, form a 5- or 6- membered heterocyclic group, which may be optionally condensed with cyclohexane or benzene or may be optionally substituted by methyl, ethyl, n- propyl, isopropyl, fluoro, chloro or bromo
• R represents non-substituted C 7 .
• 9 aralkyl or optionally substituted benzyl (substituents to the benzyl being 1 to 4 groups selected from the group consisting of halogen, C,_ 5 alkyl, C,_ 5 haloalkyl, C,_ 5 alkoxy,
• R 1 represents C,_ 5 alkyl, C,. 5 haloalkyl, C 3 . 7 cycloalkyl, C 2 . 5 alkenyl, C 2 . 5 alkinyl, optionally substituted C 7 . 9 aralkyl or optionally substituted phenyl (substituents to these groups being 1 to 4 groups selected from the group consisting of halogen, C,. 5 alkyl, C, .5 haloalkyl, C,. 5 alkoxy, C,. 5 haloalkoxy, C,_ 5 alkylthio,
• R 2 represents C,. 5 haloalkyl, C 3 or C 7 cycloalkyl or C 2 .
• 5 alkinyl, or R 1 and R 2 together with the nitrogen atom to which they are bonded, may form a 5- or 6- membered heterocyclic group, which are condensed with cyclohexane or ben- zene and may be optionally substituted by methyl, ethyl, n-propyl, isopropyl, fluoro, chloro or bromo.
• R represents a group
• R 3 and R 4 each independently represent a hydrogen atom, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, chloromethyl, trifluoromethyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, benzyl or optionally substituted phenyl (substituents to the phenyl being 1 to 2 groups selected from the group consisting of fluoro, chloro, methyl, trifluoromethyl, methoxy, tri- fluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio and nitro),
• R 3 represents phenyl, benzyl, phenethyl, 1-phenylethyl, 3-phenylpropyl, 1- methyl-2-phenylethyl, 2-methyl-2-phenylethyl, , ⁇ -dimethylbenzyl, phenoxy- methyl, 1 -phenoxy ethyl, 2-phenoxyethyl, phenylthiomethyl, 1-phenyl- thioethyl or 2-phenylthioethyl (where these groups may be substituted by 1 to 3 groups selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, iso- propoxy, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, methylthio, ehtylthio, iso-propy
• R and R each independently represent benzyl, phenethyl, 1-phenylethyl, 3-phenyl- propyl, l-methyl-2-phenylethyl, 2-methyl-2-phenylethyl, , ⁇ -dimethylbenzyl or phenyl (where these groups may be optionally substituted by 1 to 3 groups selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, n- propyl, iso-propyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, iso-propoxy, trifiuoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, methylthio, eth- ylthio, iso-propylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio, 2,2,2-trifluoroethylthio, phenyl
• R and R together with the nitrogen atom to which they are bonded, may form pyr- roli din- 1-yl, 2-methylpyrrolidin-l-yl, 2,5 -dimethylpyrrolidin- 1-yl, piperidin- 1-yl, 2-methylpiperidin-l-yl, 2,6-dimethylpiperi din- 1-yl, octahydroindol-1-yl, 2-methyloctahydroindol-l-yl, indolin-1-yl, 2-methylindolin-l-yl, 5-fluoro-2- methylindolin-1-yl, 2,3-dimethylindolin-l-yl, decahydroquinolin-1-yl, 2- methyldecahydroquinolin- 1-yl, 1 ,2,3 ,4-tetrahydroquinolin- 1 -yl, 2-methyl- 1 ,2,3,4-tetrahydroquinolin- 1 -yl, 6-
• R 1 represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, 1-chloroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cy- cloheptyl, allyl, propargyl, l-methyl-3-propinyl or l,l-dimethyl-3-propinyl, benzyl, phenethyl, 1-phenylethyl, 3-phenylpropyl, l-methyl-2-phenylethyl, 2- methyl-2-phenylethyl, ⁇ , ⁇ -dimethylbenzyl or phenyl (where these groups may be optionally substituted by 1 to 3 groups selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, n-prop
• R represents 1-chloroethyl, cyclopropyl, cycloheptyl or propargyl, or
• R and R together with the nitrogen atom to which they are bonded, may form octa- hydroindol-1-yl, 2-methyloctahydroindol-l-yl, indolin-1-yl, 2-methylindolin- 1-yl, 5-fluoro-2-methylindolin-l-yl, 2,3-dimethylindolin-l-yl, decahydro- quinolin- 1 -yl, 2-methyldecahydroquinolin- 1 -yl, 1 ,2,3 ,4-tetrahydroquinolin- 1 - yl, 2-methyl-l,2,3,4-tetrahydroquinolin-l-yl, 6-fluoro-2-methyl-l,2,3,4-tetra- hydroquinolin-1-yl, 6-chloro-2 -methyl- 1, 2,3, 4-tetrahydroquinolin- 1-yl, 2,6- dimethyl-l,2,3,4-tetrahydroquinolin-
• the carbon atom represented as C* is asymmetric carbon atom.
• the compounds of the formula (I) which are meant according to the invention are the pure, optically active enantiomers as well as mixtures in appropriate ratio of optically active enantiomers (including the racemate).
• the compounds of the above formula (I), according to the invention are optically active enantiomers or mixtures thereof.
• the starting materials (compounds of the formula (II)) in the above-mentioned preparation process a) are, except in case in which R represents non-substituted C 7 . 9 aralkyl or substituted benzyl (substituents to the benzyl being 1 to 5 groups selected from the group consisting of halogen, C,. 6 alkyl, C,. 6 haloalkyl, C,. 6 alkoxy, C,. 6 haloalkoxy, C,. 6 alkylthio, C,. 6 alkylsulfinyl, C,. 6 alkylsulphonyl, C,. 6 haloalkylthio, phenyl, phenoxy, C alkoxycarbonyl, nitro and cyano), novel compounds which were not described in the literature.
• the compounds of the formula (II) can be in general prepared, for example, by the following preparation processes b) or c).
• the compounds of the formula (IV) which are used as starting materials in the above-mentioned preparation processes b) and c) include isocyanates known in the area of organic chemistry and can be easily obtained, for example, by reacting amines represented by the formula (V)
• N,N-diethylcarbamoyl chloride N-cyclohexyl-N-ethylcarbamoyl chloride
• N,N-diallylcarbamoyl chloride N,N-dipropargylcarbamoyl chloride
• the reaction of the preparation process a) are conducted usually in an inert organic solvent.
• inert organic solvents in said reaction there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (which may optionally be chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetetrachloride, 1,2- dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, dioxane, dimethoxyethane
• DME tetrahydrofuran
• THF tetrahydrofuran
• DGM diethylene glycol dimethyl ether
• nitriles for example, acetonitrile, propionitrile
• acid amides for example, dimethylformamide
• DMF dimethylacetamide
• DMA dimethylacetamide
• HMPA hexamethylphosphoric triamide
• the preparation process a) may be conducted in the presence of an acid binding agent.
• an acid binding agent 4-dimethylaminopyridine (DMAP) can be mentioned.
• the reaction of the preparation process a) may be conducted usually at about -10 to about 200°C, preferably about 25 to about 140°C under normal pressure. Optionally it is possible to conduct it under elevated pressure or under reduced pressure.
• acid binding agents there can be mentioned inorganic salts (for example, sodium carbonate, potassium carbonate etc.), alkyl alcoholates (for example, sodium methoxide, sodium ethoxide, potassium tert- butoxide), sodium hydroxide, potassium hydroxide, lithium hydroxide, organic bases (for example, triethylamine, 1 , 1 ,4,4-tetramethylethylenediamine, N,N-dimethylani- line, pyridine etc.).
• inorganic salts for example, sodium carbonate, potassium carbonate etc.
• alkyl alcoholates for example, sodium methoxide, sodium ethoxide, potassium tert- butoxide
• sodium hydroxide potassium hydroxide
• lithium hydroxide lithium hydroxide
• organic bases for example, triethylamine, 1 , 1 ,4,4-tetramethylethylenediamine, N,N-dimethylani- line, pyridine etc.
• the compounds of the formula (I) can be selectively obtained by using DMAP as a catalyst.
• Reaction temperature in this case may be in a range of usually about 0 to about
• reaction is conducted desirably under normal pressure. Optionally, however, it is possible to conduct it under elevated pressure or under reduced pressure.
• the compounds of the formula (I), according to the present invention can be prepared, for example, by reacting 1 mole of the compound of the formula (II) with about 1 mole to about 1.5 moles of the compound of the formula (III) in the presence of about 1 mole to about 1.5 moles of DMAP as a base and in an above described inert solvent.
• the compounds of the formula (I) can also be prepared by reacting 1 mole of the compound of the formula (II) with about 1 mole to about 1.5 moles of the compound of the formula (III) in the presence of about 0.01 mole to about 0.3 moles of DMAP as a catalyst and, for example, about 1 mole to about 1.5 moles of potassium carbon- ate as a base and in such an inert solvent as described above.
• the compounds of the formula (I), according to the present invention, thus obtained can be isolated and purified, for example, by means of crystallization, chromato- graphy etc.
• the reaction of the aforementioned preparation process b) may be conducted using a boron trifiuoride-ether-complex as a catalyst.
• the reaction temperature may be usually about 0 to about 200°C, preferably about 50 to about 150°C.
• the reaction is conducted preferably under normal pressure.
• the preparation process b) may be conducted by reacting 1 mole of the compound of the formula (IV) with about 1 mole to about 2 moles of trimethylsilyl azide in the presence of about 0.005 moles to about 0.01 mole of boron trifluoride-ether-complex as a catalyst.
• the reaction of the preparation process c) may be conducted usually in a polar solvent.
• polar solvents there can be mentioned, for example, acid amides such as dimethylformamide, dimethylacetamide etc. and sufoxides such as dimethyl- sulfoxide, sulfolane etc.
• the reaction temperature may be generally about 0 to about 200°C, preferably about 20 to about 150°C.
• the reaction is conducted preferably under normal pressure. Optionally, however, it is possible to conduct it under elevated pressure or under reduced pressure.
• the preparation process c) may be conducted by reacting usually 1 mole of the compound of the formula (IV) with about 1 mole to about 1.5 moles of sodium azide in the presence of about 0.05 moles to about 1 mole of aluminium chloride as a catalyst and in a polar solvent, for example, dimethylformamide.
• the active compounds of the formula (I), according to the present invention have, as shown in the test examples, which are described later, excellent herbicidal activities and can be used as herbicidal agents for controlling weeds.
• Weeds mean, in the broadest sense, all plants which grow in locations where they are unde- sired.
• the compounds, according to the present invention act as total or selective herbicides depending upon the applied concentration.
• the active compounds of the present invention can be used, for example, as selective herbicides between the following weeds and cultures.
• plants and plant parts can be treated.
• plants includes all plants and plant populations, such as desired or undesired wild plants and cultivated plants (including naturally occurring cultivated varieties).
• Cultivated plants can be plant varieties that were obtained by conventional breeding and opti- mizing processes or by biotechnological and genetic engineering methos or a combination of such processes and methods, including transgenic plants and including plant varieties that cannot or can be protected by plant patents or plant variety rights.
• Plant parts are all parts and organs of plants occurring above or below the surface of the soil, e.g. shoots, leaves, needles, stalks and stems, trunks, flowers, fruits and seeds as well as roots, tubers, bulbs and rhizomes.
• the term plant parts also includes harvested corps and propagation material, e.g. cuttings, tubers, bulbs, rhiozomes, shoots and seeds.
• the plants and plant parts are treated using the usual methods by applying the active ingredients or compositions containing them directly to the plants or plant parts or to their surroundings (including the soil) or storeroom, e.g. by dipping, spraying, dusting, fogging, spreading and in the case of propagation material also by coating using one or multiple layers.
• the active compounds of the present invention can, depending upon the applied concentration, non-selectively control weeds and may be used, for example, on industrial terrain, rail tracks, paths, places with or without tree plantings.
• the active compounds can be used for controlling weeds in perennial cultures and applied in, for example, afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings, hopfields etc. and can be applied for the selective controlling of weeds in annual cultures.
• the active compounds of the formula (I), according to the present invention can be made into the customary formulations, when they are applied.
• formulations there can be mentioned, for example, solutions, emulsions, wettable powders, sus- pensions, powders, soluble powders, granules, tablets, suspension-emulsion concentrates, microcapsules, in polymeric substances, jumbo formulations etc.
• These formulations can be prepared according to per se known methods, for example, by mixing the active compound with extenders, namely liquid diluents and/or solid diluents or carriers, optionally with surface-active agents, namely emulsifiers and/or dispersants and/or foam-forming agents.
• extenders namely liquid diluents and/or solid diluents or carriers
• surface-active agents namely emulsifiers and/or dispersants and/or foam-forming agents.
• organic solvents can be used as auxiliary solvents.
• liquid diluents or carriers there can be mentioned generally aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chlorides, methylene chloride etc.), aliphatic hydrocarbons [for example, cyclohexane etc.
• aromatic hydrocarbons for example, xylene, toluene, alkylnaphthalene etc.
• chlorinated aromatic or chlorinated aliphatic hydrocarbons for example, chlorobenzenes, ethylene chlorides, methylene chloride etc.
• aliphatic hydrocarbons for example, cyclohexane etc.
• paraffins for example, mineral oil fractions etc.
• alcohols for example, butanol, glycols and their ethers and esters etc.
• ketones for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone etc.
• strongly polar solvents for ex- ample, dimethylformamide, dimethylsulphoxide etc.
• ground natural minerals for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth etc.
• ground synthetic minerals for example, highly dispersed silicic acid, alumina, silicates etc.
• solid carriers for granules there can be mentioned, for example, crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite, dolomite etc.), synthetic granules of inorganic and organic meals, granules of organic material (for ex- ample, sawdust, coconut shells, maize cobs and tobacco stalks etc.) etc.
• crushed and fractionated rocks for example, calcite, marble, pumice, sepiolite, dolomite etc.
• synthetic granules of inorganic and organic meals for ex- ample, sawdust, coconut shells, maize cobs and tobacco stalks etc.
• nonionic and ani- onic emulsifiers for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (for example, alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates etc.)], albumin hydrolysis products etc.
• dispersants include, for example, ligninsulphite waste liquor and methyl cellulose.
• Tackifiers may also be used in formulations (powders, granules, emulsions).
• tackifiers there can be mentioned, for example, carboxymethyl cellulose, natural and synthetic polymers (for example, gum arabic, polyvinyl alcohol, polyvinyl acetate etc.).
• Colorants may also be used.
• inorganic pigments for example, iron oxide, titanium oxide, Prussian Blue etc.
• organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs
• further trace nutrients such as salts of metals such as iron, manganese, boron, copper, cobalt, molybdenum, zinc etc.
• Said formulations can contain in a range of generally 0.1-95 % by weight, preferably 0.5-90 % by weight of the compounds of the aforementioned formula (I).
• the active compounds of the present invention can be used as such or in their formulation forms for controlling weeds. They can be used also as a mixed agent with known herbicides. Such mixed agent can be previously prepared as a final formula- tion form or can be prepared by tank-mixing on occasion of application.
• the active compounds of the formula (I) of the present invention can be used also with a safener and their application as a selective herbicide may be broadened by such a mixing.
• a safener l-( ⁇ , ⁇ -dimethylbenzyl)-3-p-tolylurea can be mentioned.
• mixed agents of some of the compounds of the formula (I) of the pres- ent invention show synergistic effects.
• active compounds of the formula (I) of the present invention can be directly used as such or used in formulation forms such as ready-to-use solutions, emulsions, suspensions, powders, granules or used in the use forms prepared by further dilution.
• the active compounds of the formula (I) of the present invention can be applied by watering, spraying, atomizing, dusting or granule application etc.
• the active compounds of the formula (I) of the present invention can be applied at any stages before and after germination of plants. They may also be mixed into the soil before sowing.
• the application amount of the active compounds may be varied in a substantial range and are fundamentally different according to the nature of the desired effect. If used as herbicides, as the application amount there can be mentioned, for example, ranges of about 0.01 to about 5 kg, preferably about 0.1 to about 3 kg of active compounds per hectare.
• l-Methyl-3-phenylpropyl isocyanate (7.68 g)
• trimethylsilyl azide (7.58 g)
• a catalytic amount of boron trifluoride-ether-complex are mixed and refluxed for 16 hours on heating.
• Test Example 1 Test for herbicidal effect against paddy field weeds
• Emulsifier Benzyloxypolyglycolether 1 part by weight
• a formulation of the active substances is obtained as emulsion by mixing 1 part by weight of an active substance with the above-mentioned amount of carrier and emulsifier. A prescribed amount of said formulation is diluted with water to prepare a formulation for testing.

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• 1999
  • 1999-07-14 JP JP11200321A patent/JP2000256331A/ja active Pending
• 2000
  • 2000-01-04 CA CA002357867A patent/CA2357867A1/en not_active Abandoned
  • 2000-01-04 WO PCT/IB2000/000008 patent/WO2000040568A1/en not_active Application Discontinuation
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