CA2204243A1 - Substituted azolyl sulphonyl uracils - Google Patents
Substituted azolyl sulphonyl uracilsInfo
- Publication number
- CA2204243A1 CA2204243A1 CA 2204243 CA2204243A CA2204243A1 CA 2204243 A1 CA2204243 A1 CA 2204243A1 CA 2204243 CA2204243 CA 2204243 CA 2204243 A CA2204243 A CA 2204243A CA 2204243 A1 CA2204243 A1 CA 2204243A1
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- substituted
- chlorine
- alkyl
- fluorine
- group
- Prior art date
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Abstract
The invention relates to novel substituted azolyl sulphonyl uracils of the general formula (I) in which Az is possibly substituted azolyl, R1 is hydrogen, cyano or halogen, R2 is cyano, nitro, halogen or a possibly substituted radical of the alkyl or alkoxy series, R3 is hydrogen, halogen, alkyl or alkyl halide, R4 is hydrogen, alkyl or halogen alkyl, and R5 is hydrogen, amino, formyl or a possibly substituted radical of the alkyl, alkenyl or alkinyl series, a process for their production and their use as herbicides.
Description
CA 02204243 1997-0~-01 ~ Le A 30 773-PCT
. ;~ 1 ~
Sul~ led azolylsulphonylph~ .racils The invention relates to novel substituted azolylsulphonylphenyluracils, a process for their preparation and their use as herbicides.
Certain heterocyclylsulphonylphenyluracils, such as, for example, the compounds 1-[2-chloro-5 -(3 ,6-dihydro-3 -methyl-2,6-dioxo-4-trifluoromethyl- 1 (2H)-pyridiminyl)-4-fluoro-phenylsulphonyl]-pyrrolidine and 4-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrirnidinyl)-4-fluoro-phenylsulphonyl]-morpholine, are known to 10 have herbicidal properties (c~ US-P 5169430). However, the activity of these compounds is not always entirely satisfactory, in particular at low application rates and active compound concentrations .
This invention, then, provides novel substituted azolylsulphonylphenyluracils of the general 15 forrnula (I) R ~ N ~0 ~0 ~ (I) in which Az represents optionally substituted azolyl, R' represents hydrogen, cyano or halogen, CA 02204243 1997-0~-01 .
. ;~ 1 ~
Sul~ led azolylsulphonylph~ .racils The invention relates to novel substituted azolylsulphonylphenyluracils, a process for their preparation and their use as herbicides.
Certain heterocyclylsulphonylphenyluracils, such as, for example, the compounds 1-[2-chloro-5 -(3 ,6-dihydro-3 -methyl-2,6-dioxo-4-trifluoromethyl- 1 (2H)-pyridiminyl)-4-fluoro-phenylsulphonyl]-pyrrolidine and 4-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrirnidinyl)-4-fluoro-phenylsulphonyl]-morpholine, are known to 10 have herbicidal properties (c~ US-P 5169430). However, the activity of these compounds is not always entirely satisfactory, in particular at low application rates and active compound concentrations .
This invention, then, provides novel substituted azolylsulphonylphenyluracils of the general 15 forrnula (I) R ~ N ~0 ~0 ~ (I) in which Az represents optionally substituted azolyl, R' represents hydrogen, cyano or halogen, CA 02204243 1997-0~-01 .
R2 represents cyano, nitro, halogen or a respectively optionally substituted radical of the group con~i~ting of alkyl and alkoxy, R3 represents hydrogen, halogen, alkyl or halogenoalkyl, R4 represents hydrogen, alkyl or halogenoalkyl, and R5 represents hydrogen, amino, formyl or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl or alkinyl.
The novel substituted azolylsulphonylphenyluracils of the general formula (I) are obtained when chlorosulphonylphenyluracils of the general formula (II) R~N~O R1 (II) ~f R2 in which R', R2, R3, R4 and R5 are each as defined above, 25 are reacted with azoles of the general formula (III) H-Az (III) in which Az is as defined above, if appropriate in the presence of a reaction auxiliary and if applopliate in the presence of a - CA 02204243 1997-0~-01 diluent.
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The novel substituted azolylsulphonylphellylulacils of the general formula (I) have a pronounced and selective herbicidal action.
s Preference is given to compounds of the formula (I) in which Az represents pyrazolyl, imid~olyl or triazolyl, each of which is optionally mono- to trisubstituted by identical or different substit~.Pnt~ from the group consisting of halogen, cyano, nitro, amino, C,-C4-alkyl, C,-C4-alkoxy, Cl-C4-alkylthio, halogeno-C,-C4-alkyl, halogeno-CI-C4-alkoxy or halogeno-CI-C4-alkylthio, Rl represents hydrogen, cyano, fluorine or chlorine, .
15 R2 represents cyano, nitro, fluorine, chlorine, bromine or a respectively optionally fluorine- and/or chlorine-substituted radical from the group consisting of C,-C4-alkyl and C,-C4-alkoxy, R3 represents hydrogen, fluorine, chlorine, bromine or optionally fluorine- and/or chlor-ine-substituted C,-C4-alkyl, R4 represents hydrogen or optionally fluorine- and/or chlorine-substituted Cl-C4-alkyl, and 25 R5 represents hydrogen, amino, formyl or a respectively optionally cyano-, fluorine-and/or chlorine-, methoxy- or ethoxy-substituted radical from the group consisting of C,-C4-alkyl, C,-C4-alkenyl and Cl-C4-alkinyl In the definitions, the saturated or ~ s~ ed hydrocarbon chains, such as alkyl, alkenyl or 30 alkinyl are in each case - even in combination with heteroatoms, such as in alkoxy - straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, CA 02204243 1997-0~-01 chlorine or bromine, in particular fluorine or chlorine.
The invention provides in particular compounds of the formula (I) in which 5 Az represents pyrazolyl or imid~701yl, each of which is optionally mono-, di- or trisubstituted by identical or different substituents from the group consisting of chlorine, bromine, methyl, ethyl or trifluoromethyl, R' represents hydrogen, fluorine or chlorine, R~ represents cyano or chlorine, R3 represents hydrogen, fluorine, chlorine, bromine or respectively optionally fluorine-and/or chlorine-substituted methyl or ethyl, R4 represents respectively optionally fluorine- and/or chlorine-substituted methyl or ethyl, and Rs represents hydrogen, amino or respectively optionally fluorine- and/or chlorine -- 20 substituted methyl, ethyl, n- or i-propyl, propenyl or propinyl The abovementioned general or preferred radical definitions apply both to the end products and to the corresponding precursors or intermediates. These radical definitions can be combined with each other as desired, that is to say combinations between the respective 25 ranges of preferred compounds are also possible.
Examples of compounds of the formula (I) are listed in groups below.
= CA 02204243 1997-0~-01 Group 1 H3Cl~ N~O H
S ~N~ (IA-l) ~ ~CI
10 Az has, for example, the mP~nin~e listed below:
pyrazol-1-yl, imi~l~7O1-l-yl, 1,2,4-triazol-1-yl, 1,3,4-triazol-1-yl, 3-methyl-pyrazol-1-yl, 4-methyl-pyrazol-1-yl, 5-methyl-pyrazol-1-yl, 3,5-dimethyl-pyrazol-1-yl, 3,4,5-trimethyl-pyrazol- 1 -yl, 4-chloro-pyrazo-1- 1 -yl, 4-bromo-pyrazol- 1 -yl, 4-chloro-3-methyl-pyrazol- 1 -yl, 15 4-bromo-3 -methyl-pyrazol- 1 -yl, 4-chloro-3 ,5 -dimethyl-pyrazol- 1 -yl, 4-bromo-3 ,5 -dimethyl-pyrazol- 1 -yl, 2-methyl-imidazol- 1 -yl, 4-methyl-imidazol- 1 -yl, 2,4-dimethyl-imidazol- 1 -yl and 3 ,5 -dimethyl- 1 ,2,4-triazol- 1 -yl.
Group 2 H3C~ N ~~ F
l I
~ N ~ (IA-2) ~ ~'CI
Az has, for example, the meanings listed above for group 1.
~' CA 02204243 1997-05-01 Group 3 Cl H3 H3C~N~~ H
~ N ~ (IA-3) ~CN
SO2-Az 10 Az has, for example, the meanings listed above for group 1.
Group 4 ; CH3 H3C~ N ~~ F
N ~ (IA~) Az has, for example, the meanings listed above for group 1.
Group S
F3C~ N ~~ H
~ N ~ (IA-5) ~CI
SO2-Az Az has, for example, the meanings listed above for group 1.
Group 6 CH, S ~ N ~ (IA-6) ~CI
10 Az has, for example, the meanings listed above for group 1.
Group 7 -F3C N ~0 H
~ N ~ (IA-7) Az has, for example, the meanings listed above for group 1.
Group 8 ~ I
~N~
SO2-Az Az has, for example, the meanings listed above for group 1.
Le A 30 773-PCT
Group 9 Cl H3 F3C N ~~ F
C~ N ~ 9) ~CI
10 Az has, for example, the meanings listed above for group 1.
Group 10 '' CIH3 F3 ~N~O F
(IA-10) Az has, for example, the meanings listed above for group 1.
Group 1 1 F3 ~ N ~O F
3 ~ ~ (IA-11) ~CI
S02-Az Az has, for example, the meanings listed above for group 1.
_ 9 _ Group 12 C~ H3 F3 ~N~O F
H3C~ ~ (IA-12) ~CN
SOa-AZ
10 Az has, for example, the meanings listed above for group 1.
Group 13 ; CHF2 ~ N ~ (IA-1 ~CI
20 Az has, for example, the meanings listed above for group 1.
Group 14 F3 ~ N ~f~O
N ~ (IA-14) --CN
Az has, for example, the meanings listed above for group 1.
Group 15 F3C N ~0 F
~, N ~ (IA-15) ~CI
Az has, for example, the ml~ning.e listed above for group 1.
Group 16 F3C~-N ~0 ~f ~ (IA-16) ~CN
Az has, for example, the mç~nin~ listed above for group 1.
Group 17 ~ ~ (IA-17) ~ ~CI
30 Az has, for example, the meanings listed above for group 1.
Group 18 ~CH3 '~ N ~ (IA-18) ~CN
Az has, for exarnple, the m~nin~ listed above for group 1.
Group 19 C~ H3 F5C2 ~ N ~f~~ F
1~ N ~ (IA-19) ~CI
Az has, for example, the me~ning~ listed above for group 1.
Group 20 Cl H3 ~ ~ F
~ N ~ (IA-20) ~CN
Az has, for example, the meanings listed above for group 1.
If,forexample,2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)-benzenesulphonyl chloride and imidazole are used as starting materials, the course of the reaction of the process according to the invention can be represented by the CA 02204243 1997-0~-01 following scheme:
CH3 ~,N Cl H3 ~ 3~ H '~N
SO2-CI ~ S~2 N,N~
~
The chlorosulphonylphenyluracils to be used as starting m~ten~l.c in the process according to the invention for pl~pa,;ng the compounds of the general formula (I) are defined in a general way by the formula (II). In the formula (II), R', R2, R3, R4 and R5 each preferably or in 15 particular have those meanings already given above in connection with the description of the compounds of the formula (I) as prefel~ed or as particularly preferred for Rl, R~, R3, R4 and R5.
The starting materials of the formula (II) are known and/or can be prepared by known 20 processes (cf. US-P 5169430).
The azoles further to be used as starting materials in the process according to the invention are defined in a general way by the formula (III). In the formula (III), Az preferably or in particular has the meaning already given above in connection with the description of the 25 compounds of the formula (I) as preferred or as particularly preferred for Az.
The starting materials of the formula (III) are known organic chemicals.
The process according to the invention is preferably carried out in the presence of a suitable 30 reaction auxiliary. Suitable reaction auxiliaries are all customary inorganic or organic bases.
These are for example alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogencarbonates, such as, for example, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium amide, sodium amide CA 02204243 1997-0~-01 or potassium amide, sodium methoxide or potassium methoxide, sodium ethoxide or potas-sium ethoxide, sodium propoxide or potassium propoxide, alulllu~iulll isopropoxide, sodium tert-butoxide or potassium tert-butoxide, sodium hydroxide or potassiurn hydroxide, ammon-ium hydroxide, sodium acetate, potassium acetate or calcium acetate, ammonium ~cet~te' S sodium carbonate, potassium calbonale or calcium carbonate, arnmonium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, and also basic organic nitrogen com-pounds such as trimethylamine, triethylamine, Ll;plo~ylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl~niline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 10 3-methyl- and 4-methyl-pyridine, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooct~ne (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
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15 Suitable diluents for carrying out the process according to the invention are the customary organic solvents. These are in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl 20 ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, or diethylene glycol dimethyl ether or diethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile, bu~ylolliLl;le or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methyl-25 pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate, ethyl acetate,n- or i-propyl acetate, or n-, i- or s-butyl acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
In the practice of the process according to the invention, the reaction temperatures may be varied over a relatively wide range. In general, tel~lpel~lures of between -10~C and +1 00~C, preferably temperatures of between 0~C and +80~C, in particular temperatures of between CA 02204243 1997-0~-01 10~C and 60~C, are employed.
The process according to the invention is generally carried out under atmospheric pres,ule.
However, it is also possible to operate under elevated or reduced pressure - in general 5 between 0.1 bar and 10 bar.
The starting materials required in each case to carry out the process according to the inven-tion are generally employed in approximately equimolar quantities. However, it is also possible to use one of the two components employed in each case in a relatively large excess.
10 The reactions are generally carried out in a suitable diluent, in the presence of an acid acceptor, and the reaction llliXlUle iS stirred for several hours at the temperature required in each case. In the process according to the invention, work-up takes place in each case according to customary methods (cf. the Plep~dlion Examples).
;
15 The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the sub-stances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotvledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, 25 Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthiurn, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
30 Dicotvledon crops of the ~enera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
- CA 02204243 1997-0~-01 MonocotYledon weeds of the ~enera: Echinochloa, Setaria, Panicum, Digit~ri~ Phleum, Poa, - Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
s Monocotyledon crops of the ~enera: Oryza, Zea, Triticum, Hordeurn, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted 10 to these genera, but also extends in the same manner to other plants.
Depending on the concentration, the compounds are suitable for total weed control, for example on in~lnetri~l terrain and rail tracks, and on paths and areas with or without tree stands. Equally, the compounds can be employed for controlling weeds in perennial crops, for 15 example forests, ornamental tree pl~nting,e, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm planta-tions, cocoa plantations, soft fruit pl~ntinge and hopfields, in lawns, turf and pastures, and for selective weed control in annual crops.
20 The compounds of the formula (I) according to the invention are suitable in particular for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both pre- and post-emergence.
The active compounds can be converted into the customary formulations, such as solutions, 25 emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active com-pound, and microencapsulations in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active 30 compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
If water is used as an extender, organic solvents can, for exarnple, also be used as auxiliary CA 02204243 1997-0~-01 solvents. Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene or alkyln~phth~lenes, chlorinated aromatics and chlorin~te~l aliphatic hydrocarbons such as chloroben7.enes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, 5 alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimelhyl~llllamide and dimethyl sulphoxide, and water.
Suitable solid carriers are:
10 for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are:
for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of 15 organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates;
suitable di~clsan~s are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, m~ng~nese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
~ CA 02204243 1997-0~-01 For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as ~ es with known herbicides, finished formulations or tank mixes being possible.
5 Suitable herbicides for the "~ixl~es are known herbicides, for example anilides such as, for example, dinurenican and propanil; arylcarboxylic acids such as, for example, dichloro-picolinic 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 ester such as, for example, diclofop-methyl, fenoxa~)rop-ethyl, fluazifop-butyl, haloxyfop-methyl 10 and quizalofop-ethyl; azinones such as, for example, chloridazon and norflurazon; carbamates such as, for example, chlorpropham, desmefliph~m, phenmediph~m and propham;
chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitro~nilin~s such as, for example, oryzalin, pendimethalin and trifluralin~, diphenyl ethers such as, for example, acifluorfen, bifenox, 15 fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, isoproluloll, linuron and methaben7thi~71-ron;
hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as, for example, imazethapyr, im~7~methabenz, im~7~pyr and im~7~quin; nitriles such as, for example, bromoxynil; dichlobenil and ioxynil;
20 oxyacetamides such as, for example, mefenacet; sulphonylureas such as, for example, amido-sulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates such as, for example, butylate, cycloate, di-allate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate; triazines such as, for 25 example, atrazine, cy~n~7.ine, sim~7.ine, simetryne, terbutryne and terbutylazine; triazinones such as, for example, hexazinone, metamitron and metribuzin; others such as, for example, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
Mixtures with other kno~vn active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil conditioners, are also possible.
CA 02204243 1997-0~-01 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 customary manner, for example by watering, spraying, atomizing or spreading.
The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essen-10 tially on the nature of the desired effect. In general, the amounts used are between 10 g and10 kg of active compound per hectare of soil surface, preferably between 50 g and 5 kg per ha.
The plepalalion and use of the active compounds according to the invention can be seen 15 from the examples which follow.
CA 02204243 1997-0~-01 Le A 30 773-PCT
~ - 19 -Plep~ation examples:
Example 1 F3C'~N~~ F
~N~
~CI
/S~2 N
A solution of 1.1 g (2.5 mmol) of 2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoro-methyl-2,6-dioxo-1(2H)-pyrimidinyl)-benzenesulphonyl chloride in 20 ml of methylene chloride is added dropwise with stirring to a mixture of 0.2 g (2.5 mmol) of pyrazole, 0.2 g of pyridine and 20 ml of methylene chloride, and the reaction mixture is stirred at about 20~C for 18 hours. The mixture is then washed twice with 0.1 N hydrochloric acid, dried with sodium sulphate and filtered. The solvent is carefully distilled off from the filtrate using a water pump vacuum.
0.7 g (62% of theory) of 1-[2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)-phenylsulphonyl]-pyrazole of melting point 172~C are obtained.
In addition, by the method of Example 1 and according to the general description of the preparation process according to the invention, for example the compounds of the formula (I) listed in Table 1 below can be prepared.
R 1~ r~
Table 1: Examples of compounds of the formula (I) Ex. R1 R' R3 R4 R5 Az Physical No. data 2 F Cl H CF3 CH3 CH3 mp.: 154~C
~, N
3 F C1 H CF3 C~3 CH3 mp.: 70~C
~, N
The novel substituted azolylsulphonylphenyluracils of the general formula (I) are obtained when chlorosulphonylphenyluracils of the general formula (II) R~N~O R1 (II) ~f R2 in which R', R2, R3, R4 and R5 are each as defined above, 25 are reacted with azoles of the general formula (III) H-Az (III) in which Az is as defined above, if appropriate in the presence of a reaction auxiliary and if applopliate in the presence of a - CA 02204243 1997-0~-01 diluent.
.
The novel substituted azolylsulphonylphellylulacils of the general formula (I) have a pronounced and selective herbicidal action.
s Preference is given to compounds of the formula (I) in which Az represents pyrazolyl, imid~olyl or triazolyl, each of which is optionally mono- to trisubstituted by identical or different substit~.Pnt~ from the group consisting of halogen, cyano, nitro, amino, C,-C4-alkyl, C,-C4-alkoxy, Cl-C4-alkylthio, halogeno-C,-C4-alkyl, halogeno-CI-C4-alkoxy or halogeno-CI-C4-alkylthio, Rl represents hydrogen, cyano, fluorine or chlorine, .
15 R2 represents cyano, nitro, fluorine, chlorine, bromine or a respectively optionally fluorine- and/or chlorine-substituted radical from the group consisting of C,-C4-alkyl and C,-C4-alkoxy, R3 represents hydrogen, fluorine, chlorine, bromine or optionally fluorine- and/or chlor-ine-substituted C,-C4-alkyl, R4 represents hydrogen or optionally fluorine- and/or chlorine-substituted Cl-C4-alkyl, and 25 R5 represents hydrogen, amino, formyl or a respectively optionally cyano-, fluorine-and/or chlorine-, methoxy- or ethoxy-substituted radical from the group consisting of C,-C4-alkyl, C,-C4-alkenyl and Cl-C4-alkinyl In the definitions, the saturated or ~ s~ ed hydrocarbon chains, such as alkyl, alkenyl or 30 alkinyl are in each case - even in combination with heteroatoms, such as in alkoxy - straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, CA 02204243 1997-0~-01 chlorine or bromine, in particular fluorine or chlorine.
The invention provides in particular compounds of the formula (I) in which 5 Az represents pyrazolyl or imid~701yl, each of which is optionally mono-, di- or trisubstituted by identical or different substituents from the group consisting of chlorine, bromine, methyl, ethyl or trifluoromethyl, R' represents hydrogen, fluorine or chlorine, R~ represents cyano or chlorine, R3 represents hydrogen, fluorine, chlorine, bromine or respectively optionally fluorine-and/or chlorine-substituted methyl or ethyl, R4 represents respectively optionally fluorine- and/or chlorine-substituted methyl or ethyl, and Rs represents hydrogen, amino or respectively optionally fluorine- and/or chlorine -- 20 substituted methyl, ethyl, n- or i-propyl, propenyl or propinyl The abovementioned general or preferred radical definitions apply both to the end products and to the corresponding precursors or intermediates. These radical definitions can be combined with each other as desired, that is to say combinations between the respective 25 ranges of preferred compounds are also possible.
Examples of compounds of the formula (I) are listed in groups below.
= CA 02204243 1997-0~-01 Group 1 H3Cl~ N~O H
S ~N~ (IA-l) ~ ~CI
10 Az has, for example, the mP~nin~e listed below:
pyrazol-1-yl, imi~l~7O1-l-yl, 1,2,4-triazol-1-yl, 1,3,4-triazol-1-yl, 3-methyl-pyrazol-1-yl, 4-methyl-pyrazol-1-yl, 5-methyl-pyrazol-1-yl, 3,5-dimethyl-pyrazol-1-yl, 3,4,5-trimethyl-pyrazol- 1 -yl, 4-chloro-pyrazo-1- 1 -yl, 4-bromo-pyrazol- 1 -yl, 4-chloro-3-methyl-pyrazol- 1 -yl, 15 4-bromo-3 -methyl-pyrazol- 1 -yl, 4-chloro-3 ,5 -dimethyl-pyrazol- 1 -yl, 4-bromo-3 ,5 -dimethyl-pyrazol- 1 -yl, 2-methyl-imidazol- 1 -yl, 4-methyl-imidazol- 1 -yl, 2,4-dimethyl-imidazol- 1 -yl and 3 ,5 -dimethyl- 1 ,2,4-triazol- 1 -yl.
Group 2 H3C~ N ~~ F
l I
~ N ~ (IA-2) ~ ~'CI
Az has, for example, the meanings listed above for group 1.
~' CA 02204243 1997-05-01 Group 3 Cl H3 H3C~N~~ H
~ N ~ (IA-3) ~CN
SO2-Az 10 Az has, for example, the meanings listed above for group 1.
Group 4 ; CH3 H3C~ N ~~ F
N ~ (IA~) Az has, for example, the meanings listed above for group 1.
Group S
F3C~ N ~~ H
~ N ~ (IA-5) ~CI
SO2-Az Az has, for example, the meanings listed above for group 1.
Group 6 CH, S ~ N ~ (IA-6) ~CI
10 Az has, for example, the meanings listed above for group 1.
Group 7 -F3C N ~0 H
~ N ~ (IA-7) Az has, for example, the meanings listed above for group 1.
Group 8 ~ I
~N~
SO2-Az Az has, for example, the meanings listed above for group 1.
Le A 30 773-PCT
Group 9 Cl H3 F3C N ~~ F
C~ N ~ 9) ~CI
10 Az has, for example, the meanings listed above for group 1.
Group 10 '' CIH3 F3 ~N~O F
(IA-10) Az has, for example, the meanings listed above for group 1.
Group 1 1 F3 ~ N ~O F
3 ~ ~ (IA-11) ~CI
S02-Az Az has, for example, the meanings listed above for group 1.
_ 9 _ Group 12 C~ H3 F3 ~N~O F
H3C~ ~ (IA-12) ~CN
SOa-AZ
10 Az has, for example, the meanings listed above for group 1.
Group 13 ; CHF2 ~ N ~ (IA-1 ~CI
20 Az has, for example, the meanings listed above for group 1.
Group 14 F3 ~ N ~f~O
N ~ (IA-14) --CN
Az has, for example, the meanings listed above for group 1.
Group 15 F3C N ~0 F
~, N ~ (IA-15) ~CI
Az has, for example, the ml~ning.e listed above for group 1.
Group 16 F3C~-N ~0 ~f ~ (IA-16) ~CN
Az has, for example, the mç~nin~ listed above for group 1.
Group 17 ~ ~ (IA-17) ~ ~CI
30 Az has, for example, the meanings listed above for group 1.
Group 18 ~CH3 '~ N ~ (IA-18) ~CN
Az has, for exarnple, the m~nin~ listed above for group 1.
Group 19 C~ H3 F5C2 ~ N ~f~~ F
1~ N ~ (IA-19) ~CI
Az has, for example, the me~ning~ listed above for group 1.
Group 20 Cl H3 ~ ~ F
~ N ~ (IA-20) ~CN
Az has, for example, the meanings listed above for group 1.
If,forexample,2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)-benzenesulphonyl chloride and imidazole are used as starting materials, the course of the reaction of the process according to the invention can be represented by the CA 02204243 1997-0~-01 following scheme:
CH3 ~,N Cl H3 ~ 3~ H '~N
SO2-CI ~ S~2 N,N~
~
The chlorosulphonylphenyluracils to be used as starting m~ten~l.c in the process according to the invention for pl~pa,;ng the compounds of the general formula (I) are defined in a general way by the formula (II). In the formula (II), R', R2, R3, R4 and R5 each preferably or in 15 particular have those meanings already given above in connection with the description of the compounds of the formula (I) as prefel~ed or as particularly preferred for Rl, R~, R3, R4 and R5.
The starting materials of the formula (II) are known and/or can be prepared by known 20 processes (cf. US-P 5169430).
The azoles further to be used as starting materials in the process according to the invention are defined in a general way by the formula (III). In the formula (III), Az preferably or in particular has the meaning already given above in connection with the description of the 25 compounds of the formula (I) as preferred or as particularly preferred for Az.
The starting materials of the formula (III) are known organic chemicals.
The process according to the invention is preferably carried out in the presence of a suitable 30 reaction auxiliary. Suitable reaction auxiliaries are all customary inorganic or organic bases.
These are for example alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogencarbonates, such as, for example, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium amide, sodium amide CA 02204243 1997-0~-01 or potassium amide, sodium methoxide or potassium methoxide, sodium ethoxide or potas-sium ethoxide, sodium propoxide or potassium propoxide, alulllu~iulll isopropoxide, sodium tert-butoxide or potassium tert-butoxide, sodium hydroxide or potassiurn hydroxide, ammon-ium hydroxide, sodium acetate, potassium acetate or calcium acetate, ammonium ~cet~te' S sodium carbonate, potassium calbonale or calcium carbonate, arnmonium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate, and also basic organic nitrogen com-pounds such as trimethylamine, triethylamine, Ll;plo~ylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl~niline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 10 3-methyl- and 4-methyl-pyridine, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooct~ne (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
.
15 Suitable diluents for carrying out the process according to the invention are the customary organic solvents. These are in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl 20 ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, or diethylene glycol dimethyl ether or diethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile, bu~ylolliLl;le or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methyl-25 pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate, ethyl acetate,n- or i-propyl acetate, or n-, i- or s-butyl acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
In the practice of the process according to the invention, the reaction temperatures may be varied over a relatively wide range. In general, tel~lpel~lures of between -10~C and +1 00~C, preferably temperatures of between 0~C and +80~C, in particular temperatures of between CA 02204243 1997-0~-01 10~C and 60~C, are employed.
The process according to the invention is generally carried out under atmospheric pres,ule.
However, it is also possible to operate under elevated or reduced pressure - in general 5 between 0.1 bar and 10 bar.
The starting materials required in each case to carry out the process according to the inven-tion are generally employed in approximately equimolar quantities. However, it is also possible to use one of the two components employed in each case in a relatively large excess.
10 The reactions are generally carried out in a suitable diluent, in the presence of an acid acceptor, and the reaction llliXlUle iS stirred for several hours at the temperature required in each case. In the process according to the invention, work-up takes place in each case according to customary methods (cf. the Plep~dlion Examples).
;
15 The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the sub-stances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotvledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, 25 Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthiurn, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
30 Dicotvledon crops of the ~enera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
- CA 02204243 1997-0~-01 MonocotYledon weeds of the ~enera: Echinochloa, Setaria, Panicum, Digit~ri~ Phleum, Poa, - Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
s Monocotyledon crops of the ~enera: Oryza, Zea, Triticum, Hordeurn, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted 10 to these genera, but also extends in the same manner to other plants.
Depending on the concentration, the compounds are suitable for total weed control, for example on in~lnetri~l terrain and rail tracks, and on paths and areas with or without tree stands. Equally, the compounds can be employed for controlling weeds in perennial crops, for 15 example forests, ornamental tree pl~nting,e, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm planta-tions, cocoa plantations, soft fruit pl~ntinge and hopfields, in lawns, turf and pastures, and for selective weed control in annual crops.
20 The compounds of the formula (I) according to the invention are suitable in particular for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both pre- and post-emergence.
The active compounds can be converted into the customary formulations, such as solutions, 25 emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active com-pound, and microencapsulations in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active 30 compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
If water is used as an extender, organic solvents can, for exarnple, also be used as auxiliary CA 02204243 1997-0~-01 solvents. Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene or alkyln~phth~lenes, chlorinated aromatics and chlorin~te~l aliphatic hydrocarbons such as chloroben7.enes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, 5 alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimelhyl~llllamide and dimethyl sulphoxide, and water.
Suitable solid carriers are:
10 for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are:
for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of 15 organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates;
suitable di~clsan~s are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, m~ng~nese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
~ CA 02204243 1997-0~-01 For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as ~ es with known herbicides, finished formulations or tank mixes being possible.
5 Suitable herbicides for the "~ixl~es are known herbicides, for example anilides such as, for example, dinurenican and propanil; arylcarboxylic acids such as, for example, dichloro-picolinic 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 ester such as, for example, diclofop-methyl, fenoxa~)rop-ethyl, fluazifop-butyl, haloxyfop-methyl 10 and quizalofop-ethyl; azinones such as, for example, chloridazon and norflurazon; carbamates such as, for example, chlorpropham, desmefliph~m, phenmediph~m and propham;
chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitro~nilin~s such as, for example, oryzalin, pendimethalin and trifluralin~, diphenyl ethers such as, for example, acifluorfen, bifenox, 15 fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, isoproluloll, linuron and methaben7thi~71-ron;
hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as, for example, imazethapyr, im~7~methabenz, im~7~pyr and im~7~quin; nitriles such as, for example, bromoxynil; dichlobenil and ioxynil;
20 oxyacetamides such as, for example, mefenacet; sulphonylureas such as, for example, amido-sulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates such as, for example, butylate, cycloate, di-allate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate; triazines such as, for 25 example, atrazine, cy~n~7.ine, sim~7.ine, simetryne, terbutryne and terbutylazine; triazinones such as, for example, hexazinone, metamitron and metribuzin; others such as, for example, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
Mixtures with other kno~vn active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil conditioners, are also possible.
CA 02204243 1997-0~-01 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 customary manner, for example by watering, spraying, atomizing or spreading.
The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essen-10 tially on the nature of the desired effect. In general, the amounts used are between 10 g and10 kg of active compound per hectare of soil surface, preferably between 50 g and 5 kg per ha.
The plepalalion and use of the active compounds according to the invention can be seen 15 from the examples which follow.
CA 02204243 1997-0~-01 Le A 30 773-PCT
~ - 19 -Plep~ation examples:
Example 1 F3C'~N~~ F
~N~
~CI
/S~2 N
A solution of 1.1 g (2.5 mmol) of 2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoro-methyl-2,6-dioxo-1(2H)-pyrimidinyl)-benzenesulphonyl chloride in 20 ml of methylene chloride is added dropwise with stirring to a mixture of 0.2 g (2.5 mmol) of pyrazole, 0.2 g of pyridine and 20 ml of methylene chloride, and the reaction mixture is stirred at about 20~C for 18 hours. The mixture is then washed twice with 0.1 N hydrochloric acid, dried with sodium sulphate and filtered. The solvent is carefully distilled off from the filtrate using a water pump vacuum.
0.7 g (62% of theory) of 1-[2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)-phenylsulphonyl]-pyrazole of melting point 172~C are obtained.
In addition, by the method of Example 1 and according to the general description of the preparation process according to the invention, for example the compounds of the formula (I) listed in Table 1 below can be prepared.
R 1~ r~
Table 1: Examples of compounds of the formula (I) Ex. R1 R' R3 R4 R5 Az Physical No. data 2 F Cl H CF3 CH3 CH3 mp.: 154~C
~, N
3 F C1 H CF3 C~3 CH3 mp.: 70~C
~, N
4 F Cl H CF3 CH3 c~, mp.: 67~C
H,C~I ,N
F Cl H CF3 CH3 ~' CH, mp.: 75~C
H,C 7 6 F Cl H CF3 CH3 Br CH~ mp: 1 75~C
N
.
Table 1 - continued Ex. Rl R2 R3 R4 Rs Az Physical No. data 7 F Cl H ~3 H ~ CH, mp.: 235~C
H,C~I
8 F Cl H CF3 H Br CH, IH~
~N ~I)MS~-N D6, d): 6.47 ppm 9 F cl H CF3 CH3 ~ c~, mp.: 141~C
~, N
~,C N
CA 02204243 1997-0~-01 ~ - - 22 -Use Examples:
FY~mple A
H,C~I ,N
F Cl H CF3 CH3 ~' CH, mp.: 75~C
H,C 7 6 F Cl H CF3 CH3 Br CH~ mp: 1 75~C
N
.
Table 1 - continued Ex. Rl R2 R3 R4 Rs Az Physical No. data 7 F Cl H ~3 H ~ CH, mp.: 235~C
H,C~I
8 F Cl H CF3 H Br CH, IH~
~N ~I)MS~-N D6, d): 6.47 ppm 9 F cl H CF3 CH3 ~ c~, mp.: 141~C
~, N
~,C N
CA 02204243 1997-0~-01 ~ - - 22 -Use Examples:
FY~mple A
5 Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether 10 To produce a suitable ~lepaldlion of 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, after 24 hours, watered with the 15 preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the plepaldlion is of no importance.
Only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% = no action (like untreated control) 100% = total destruction 25 In this test, for example the compounds obtained by preparation examples 1 and 2 are well tolerated by crops, such as, for example, barley (10%), and exhibit strong activity against weeds, such as, for example, digitaria (95-100%), panicum (100%), chenopodiurn (100%) and polygonum (100%).
CA 02204243 1997-0~-01 Example B
Pre-emergence test / outdoor S Solvent: 5 parts by weight of acetone Fm~ ifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable plepaldlion of 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 10 concentrate is diluted with water to the desired concentration.
Shortly after sowing the seeds of the test plants in the field, the individual plots were watered with the amount of active compound pl~paldlion necessary for wetting the soil surface evenly. The concentration of the active compound in the plepaldlion is of no importance, 15 only the amount of active compound applied per unit area being decisive.
After S weeks, the degree of damage to the test plants is rated in % damage in comparison to the untreated control.
20 The figures denote:
0% = no action 100% = total destruction.
In this test, for example the compounds obtained by plep~dlion examples 1, 2 and 3 are well 25 tolerated by crops, such as, for example, barley (15-20%), and exhibit strong activity against weeds such as, for example, amborosia (70-95%), chenopodium (70-90%), polygonom (99-100%) and viola (90-95%).
Seeds of the test plants are- sown in normal soil and, after 24 hours, watered with the 15 preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the plepaldlion is of no importance.
Only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% = no action (like untreated control) 100% = total destruction 25 In this test, for example the compounds obtained by preparation examples 1 and 2 are well tolerated by crops, such as, for example, barley (10%), and exhibit strong activity against weeds, such as, for example, digitaria (95-100%), panicum (100%), chenopodiurn (100%) and polygonum (100%).
CA 02204243 1997-0~-01 Example B
Pre-emergence test / outdoor S Solvent: 5 parts by weight of acetone Fm~ ifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable plepaldlion of 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 10 concentrate is diluted with water to the desired concentration.
Shortly after sowing the seeds of the test plants in the field, the individual plots were watered with the amount of active compound pl~paldlion necessary for wetting the soil surface evenly. The concentration of the active compound in the plepaldlion is of no importance, 15 only the amount of active compound applied per unit area being decisive.
After S weeks, the degree of damage to the test plants is rated in % damage in comparison to the untreated control.
20 The figures denote:
0% = no action 100% = total destruction.
In this test, for example the compounds obtained by plep~dlion examples 1, 2 and 3 are well 25 tolerated by crops, such as, for example, barley (15-20%), and exhibit strong activity against weeds such as, for example, amborosia (70-95%), chenopodium (70-90%), polygonom (99-100%) and viola (90-95%).
Claims (8)
1. Substituted azolylsulphonylphenyluracils of the general formula (I) (I) in which Az represents optionally substituted azolyl, R1 represents hydrogen, cyano or halogen, R2 represents cyano, nitro, halogen or a respectively optionally substituted radical of the group consisting of alkyl and alkoxy, R3 represents hydrogen, halogen, alkyl or halogenoalkyl, R4 represents hydrogen, alkyl or halogenoalkyl, and R5 represents hydrogen, amino, formyl or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl or alkinyl.
2. Substituted azolylsulphonylphenyluracils of the general formula (I) according to Claim 1, characterized in that Az represents pyrazolyl, imidazolyl or triazolyl, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, amino, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, halogeno-C1-C4-alkyl, halogeno-C1-C4-alkoxy or halogeno-C1-C4-alkylthio, R1 represents hydrogen, cyano, fluorine or chlorine, R2 represents cyano, nitro, fluorine, chlorine, bromine or a respectively optionally fluorine- and/or chlorine-substituted radical from the group consisting of C1-C4-alkyl and C1-C4-alkoxy, R3 represents hydrogen, fluorine, chlorine, bromine or optionally fluorine- and/or chlorine-substituted C1-C4-alkyl, R4 represents hydrogen or optionally fluorine- and/or chlorine-substituted C1-C4-alkyl, and R5 represents hydrogen, amino, formyl or a respectively optionally cyano-, fluorine- and/or chlorine-, methoxy- or ethoxy-substituted radical from the group consisting of C1-C4-alkyl, C1-C4-alkenyl and C1-C4-alkinyl.
3. Substituted azolylsulphonylphenyluracils of the general formula (I) according to Claim 1, characterized in that Az represents pyrazolyl or imidazolyl, each of which is optionally mono-, di- ortrisubstituted by identical or different substituents from the group consisting of chlorine, bromine, methyl, ethyl or trifluoromethyl, R1 represents hydrogen, fluorine or chlorine, R2 represents cyano or chlorine, R3 represents hydrogen, fluorine, chlorine, bromine or respectively optionally fluorine- and/or chlorine-substituted methyl or ethyl, R4 represents respectively optionally fluorine- and/or chlorine-substituted methyl or ethyl, and R5 represents hydrogen, amino or respectively optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, propenyl or propinyl.
4. Process for preparing substituted azolylsulphonylphenyluracils of the general formula (I) (I), in which R1, R2, R3, R4, R5 and Az are each as defined in Claim 1, characterized in that chlorosulphonylphenyluracils of the general formula (II) (II) in which R1, R2, R3, R4 and R5 are each as defined in Claim 1, are reacted with azoles of the general formula (III) H-Az (III) in which Az is as defined in Claim 1, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
5. Herbicidal compositions, characterized in that they comprise at least one substituted azolylsulphonylphenyluracil of the general formula (I) according to Claims 1 to 4.
6. Method for controlling undesired plants, characterized in that substituted azolylsulphonylphenyluracils of the general formula (I) according to Claims 1 to 4 are allowed to act on undesired plants and/or their habitat.
7. Use of substituted azolylsulphonylphenyluracils of the general formula (I) according to Claims 1 to 4 for controlling undesired plants.
8. Process for preparing herbicidal compositions, characterized in that substituted azolylsulphonylphenyluracils of the general formula (I) according to Claims 1 to 4 are mixed with extenders and/or surface-active agents.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4439332.6 | 1994-11-04 | ||
| DE4439332A DE4439332A1 (en) | 1994-11-04 | 1994-11-04 | Substituted Azolylsulfonylphenyluracile |
| PCT/EP1995/004146 WO1996014315A1 (en) | 1994-11-04 | 1995-10-23 | Substituted azolyl sulphonyl uracils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2204243A1 true CA2204243A1 (en) | 1996-05-17 |
Family
ID=29403401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2204243 Abandoned CA2204243A1 (en) | 1994-11-04 | 1995-10-23 | Substituted azolyl sulphonyl uracils |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2204243A1 (en) |
-
1995
- 1995-10-23 CA CA 2204243 patent/CA2204243A1/en not_active Abandoned
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