CH487591A - Herbicides - Google Patents

Description

  

  



     Herbicides
Patent No. 482 402 describes new weed control agents which contain an inert carrier and a 3-substituted uracil of the general formula in an amount corresponding to the desired herbicidal effect
EMI1.1
 wherein R, is a radical with a molecular weight of
15 to 250, namely unsubstituted alkyl radical with l to
10 carbon atoms, an alkyl radical substituted by one or more chlorine or bromine atoms, hydroxy, alkoxy, alkoxycarbonyl and cyano radical (s), an unsubstituted alkenyl or alkynyl radical, a given one by a (s) ) or several fluorine, bromine or chlorine atom (s)

  , Hydroxy, alkoxy, cyano, alkyl mercapto, alkyl, chloroalkyl, nitro or trifluoromethyl radical (s) substituted aryl or aralkyl radical, if necessary by one or more fluorine, bromine or chlorine atom (e ), Alkoxy or alkyl radical (s) substituted cycloalkyl radical or a cyclo alkenyl radical optionally substituted by one or more alkoxy radical (s), R represents a radical with a molecular weight of 1 to 250, namely an alkyl mercapto, alkoxy, alkenyl, Cyano, thiocyanate or nitro radical, a halogen or hydrogen atom, a methyl thiol radical optionally substituted by one or more alkyl radical (s) or a methyl thiol radical optionally substituted by one (s)

   or a plurality of fluorine, bromine or chlorine atom (s), cyano, mercapto, alkoxy or hydroxy radical (s) is a substituted alkyl radical, R.; represents a radical with a molecular weight of I to 200, namely an alkyl, alkoxy or haloalkyl radical or a hydrogen, chlorine or bromine atom, where R. and R3 form a divalent a) ky) ene bridge of the formula (CH2) a.

   in which n is 3, 4 or 5 can be combined with one another, R4 is a radical with a molecular weight of I to 250, namely a dialkoxyphosphinyl, alkenyl or alkynyl radical, a hydrogen atom, one optionally by an or several bromine or chlorine atom (s), hydroxy, alkoxy, alkoxycarbonyl, cyano or carboxy radical (s) substituted alkyl radical, a carbamyl or thiocarbamyl radical optionally substituted by one or more alkyl, phenyl or chlorophenyl radical (s), optionally with a ( en) or several bromine, chlorine or fluorine atom (s),
Alkyl, nitro or alkoxy radical (s) substituted phenyl mercapto radical, one optionally substituted by one or more bromine, chlorine or fluorine atom (s)

   substituted
Alkylmercapto radical or an acyl radical, which is characterized by one or more phenyl radical (c), which may optionally contain one or more chlorine or bromine atoms, or by one or more phenoxy radical (s), which can contain one or more chlorine or bromine atom (s), can be substituted, X represents an oxygen or sulfur atom, where. if both R2 and RA are hydrogen atoms, either R:;

   an alkyl radical with I to 6 carbon atoms and R, an alkyl radical with 3 to 6 carbon atoms, an allyl or propynyl radical or a cycloalkyl or cycloalkenyl radical with 5 to 8 carbon atoms or R: a hydrogen atom and Ri a cycloalkyl or cycloalkenyl radical with 5 to 8 Represent carbon atoms and where, if R, pure hydrogen atom and R represent a methyl radical, R represents a cycloalkyl or cycloalkenyl radical having 5 to 8 carbon atoms, and / or contain its metal salt.



   In the course of further developments in this field, it has now been found that 3-substituted uracils which essentially correspond to formula (1) with the modification that the 3-substituent (Ri) is cycloalkylalkyl or cycloalkenylalkyl, and their metal salts are excellent herbicides.



   According to the invention with regard to their effectiveness as herbicides at lower dosages, preference is given to compounds of the formula (1) in which R 1 is (substituted cycloalkyl) -alkyl with a total of 5 to 14 carbon atoms, in particular in the case of R: i is methyl , R. chlorine, bromine, iodine, methyl, hydroxymethyl and methoxymethyl, R: l hydrogen or methyl and R4 hydrogen.



   When mentioning salts, this includes the compounds that are linked with cations such as sodium, potassium, lithium, calcium, magnesium,
Barium, strontium, iron, manganese and quaternary
Ammonium can be obtained.



   The terms cycloalkylalkyl and aCyclo- alkenylatkyh) include, without this being exhaustive
List represents: cyclohexylalkyl, cyclohexenylalkyl
Cyclopentylalkyl, cyclopentenylalkyl,
Norbornylalkyl, norbornenylalkyl,
Bicyclo- (2,2,2) -octylalkyl,
Bicyclo (-2,2,2) octenylalkyl,
Cyclobutylalkyl, cyclobutenylalkyl,
Hexahydroindenylalkyl, tetrahydroindanylalkyl, hexahydroindanylalkyl,
Hexahydro-4,7-methanoindenylalkyl, hexahydro-4, 7-methanoindanylalkyl,
Tetrahydro-4,7-methanoindanylalkyl,
Decahydronaphthylalkyl,
Tetrahydronaphthylalkyl, decahydro-1, 4-methanonaphthylalkyl, octahydro-1, 4-methanonaphthylalkyl, decahydro-1, 4,5,8-dimethanonaphthylalkyl,

  
Octahydro-1, 4,5,8-dimethanonaphthylalkyl.



   These cyclic substituents can be further substituted with alkyl groups having 1 to 4 carbon atoms, methoxy, chlorine and bromine.



   The above novel uracils can be prepared according to the methods described in the literature and particularly the methods described in Patent No. 482,402.



   The production can e.g. B. be done by converting a monosubstituted urea or thiourea with a / 3-ketoester in the presence of an acid to form a 2,3-unsaturated 3- (3-substituted ureido) ester and then heating it with a strong base. This causes a ring closure and the corresponding salt of the 3-substituted uracil is obtained.



  If desired, this salt can be converted into the 3-substituted uracil by reaction with an acid.



   This three-step reaction sequence is explained using the same terminology by the following equations:
EMI2.1


<tb> <SEP> X <SEP> O <SEP> O <SEP> X <SEP> R3 <SEP> O
<tb> <SEP> !! <SEP>! <SEP> H <SEP>! <SEP>! <SEP> acid <SEP>! <SEP> H <SEP>!
<tb> R, <SEP> NHCNH = -f-R'OC-C-C-R3 <SEP> R1NHC-N-C = C-COR'-f-H20 <SEP> i
<tb> <SEP> a
<tb> <SEP>! <SEP> margin no
<tb> <SEP> K2 <SEP> lez
<tb> <SEP> 0
<tb> <SEP> Base
<tb> X <SEP> R3 <SEP> O <SEP> \ <SEP> Re
<tb> RINHCNHC = C-COR'R, -N <SEP> m
<tb> <SEP> I
<tb> <SEP> to
<tb> <SEP> Rp <SEP> x // "\ <SEP> N <SEP> R3
<tb> <SEP> O <SEP> c <SEP> O
<tb> <SEP> O
<tb> <SEP> Ri-N <SEP> Sdure) <SEP> I \ / R2
<tb> <SEP> Sauré
<tb> <SEP> Ri-N <SEP> m <SEP> (D <SEP> RI-N
<tb> <SEP> X <SEP> N <SEP> R3 <SEP> X <SEP> N <SEP> R3
<tb> <SEP> X <SEP> R3-H
<tb>
Here, R 'is an alkyl radical having 1 to 6 carbon atoms.



   If R7 and R4 are hydrogen and R: i is formed by alkyte, these uracils can also be obtained according to the following equations. will be provided:
EMI3.1


<tb> <SEP> NH2
<tb> <SEP> I <SEP> H
<tb> <SEP> CH3C === C-COOCzH5 + <SEP> <9 <SEP> N = C = O
<tb> <SEP> H
<tb> CH3C = CCOOC2Hs <SEP> ---- CHa-C-CH2COOC2H5
<tb> <SEP> N <SEP> H <SEP> (tautomeric <SEP> forms) <SEP> N
<tb> <SEP> C <SEP> ONaOH <SEP> C = O
<tb> / \ <SEP> x3NaOH <SEP> i <SEP> ¯ \
<tb> <SEP> NH \ / &commat; (DHCI <SEP> NH - / "
<tb> <SEP> O
<tb> <SEP> 0
<tb> <SEP> N) <SEP> + S
<tb> <SEP> o <SEP> N <SEP> CH3
<tb> <SEP> H
<tb> <SEP> 0 <SEP> N <SEP> cHs
<tb>
These uraciles give the farmer and landowner a new weapon for combating unwanted vegetation.

   The compounds are unique in that they are effective against broad-leaved weeds as well as grass weeds, the difficult-to-kill Cyperus and perennial grasses such as Agropyron repens, Sorghum halepense and Cynodon dactylon, and on strong, adsorptive substrates such as railway gravel, heavy clay soil and soils rich in organic matter to be effective.



   So could z. B. by treatment before emergence, broad-leaved weeds, such as Amaranthus sp., Chenopodium album, Brassica, Stellaria sp. and Ambrosia artemisiifolia, and grass weeds such as Digitaria sp. and Setaria sp., and the uracils can also be used to treat the soil and foliage in order to treat broadleaf weeds such as Amaranthus sp., Chenopodium album, Brassica, Stellaria sp.

   and Ambrosia artemisiifolia, and grass weeds such as Digitaria sp., Setaria sp., Agropyron repens and young sorghum halepense
Due to this combination of properties, the compounds are suitable as soil sterilizing agents and in all cases in which general weed control is desired, such as industrial sites, railroad areas and the areas adjacent to the crops in agricultural areas.



   Certain of the uracils also develop a selective herbicidal effect in crops. By suitable choice of a uracil according to the invention and the dosage and application time, annual griser and young broad-leaved weeds can be planted in useful crops, such as asparagus, corn, flax, sugar cane, safflower, peanut, lemon, alfalfa, strawberry, gladiolus, stone fruits , Sorghum, sugar beet, beetroot, beetroot, spinach, potatoes, pineapple, cotton and pumpkin.



   With a suitable choice of the dosage and the time of application, certain uracils can also be used to control weeds in dormant crops.



   Many of the compounds have unusually good oil solubility and are thus suitable for application in sols such as weed control oils, diesel oil, luminous oil, xylene and other commercially available spray oils. The good oil solubility makes the shipping of many uracil-O1 concentrates practical. Such concentrates can be diluted with cheap diesel oil and with weed control oils at the point of use.



   The exact amounts of uracils to be used in the given case depend of course on the desired end result, the intended use, the plants and soil present, the preparation used, the type of application, the prevailing weather conditions, the leaf density and similar factors. In view of this multitude of variables, it is impossible to state a dosage that is applicable in all cases. In general, the compounds are used for general weed control in dosages of about 0.28 to 90 kg / ha. In the selective weed control in useful plants, dosages of 0.28 or 0.56 to 3.4 or 9.0 kg / ha are generally used, and in the preventive treatment with z. B. Compounds of formula (7) and formula (9) can be, for. B. with 0.28 to 5.6, preferably 0.56 to 2.2, or 4.5 kg / ha or with z. B.



  Compounds of the formula (13) with 0.56 to 5.6 or with compounds of the formula (11) with 0.56 to 4.5 kg / ha. To combat species that are difficult to kill and grow under unfavorable conditions, larger amounts of the active ingredient can be used. Due to economic factors, such as the inaccessibility of the area to be treated, e.g. B. in firebreaks in forests, less frequent treatment with higher doses can be beneficial.



   As described in detail in Patent No. 482,402, the preparation of the uracil compounds for use as herbicides can be accomplished by mixing with them conventional adjuvants, including surfactants.



   The uracil salts are particularly advantageous for use as herbicides because they are water-soluble and can be used in aqueous solutions.



   The weed control compositions according to the invention can also be formulated so that they contain two or more of the uracils. You can also use the
Uracile also have a content of other, known herbicides, it being possible to obtain agents which have advantages beyond their individual components.



   The well-known herbicides that can be combined with the uracils of the formula (1) include, inter alia: Siibstituted ureas
3- (3,4-dichlorophenyl) -1,1-dimethylurea, 3- (4-chlorophenyl) -1,1-dimethylurea,
3-phenyl-1,1-dimethylurea,
3- (3,4-dichlorophenyl) -3-methoxy-1,1-dimethyl urea, 3- (4-chlorophenyl) -3-methoxy-l, l-dimethyl urea,
3- (3,4-dichlorophenyl) -1-n-butyl-1-methyl urea,
3- (3,4-dichlorophenyl) -1-methoxy-1-methyl urea, 3- (4-chlorophenyl) -l-methoxy-l-methyl urea,
3- (3, 3-dichlorophenyl) -1, 1, 3-trimethylurea,
3- (3, 4-dichlorophenyl) -1, 1-diethylurea,
3- (p-chlorophenoxyphenyl) -1, 1-dimerhyl urea.



   These ureas can be mixed with the uracils according to the invention in ratios of 1: 4 to 4: 1, a ratio of 1: 2 to 2: 1 being preferred.



   Substituted triazines
2-chloro-4,6-bis- (ethylamino) -s-triazine, 2-chloro-4-ethylamino-6-isopropylamino-s-triazine,
2-chloro-4, 6-bis (methoxypropylamino) -sXtriazine,
2-methoxy-4,5-bis (isopropylamino) -s-triazine,
2-diethylamino-4-isopropylacetamido-6-methoxy s-triazine,
2-isopropylamino-4-methoxyethylamino-6-methyl mercapto-s-triazine, 2-methylmercapto-4, 6-bis (isopropylamino) -s-triazine,
2-ethylmercapto-4,6-bis- (ethylamino) -s-triazine, 2-methylmercapto-4-ethylamino-6-isopropyl-amino-s-triazine,
2-methoxy-4, 6-bis- (ethylamino) -s-triazine, 2-methoxy-4-ethylamino-6-isopropylamino- s-triazine, 2-chloro-4, 6-bis (isopropylamino) -s- triazine.



   The triazines can be mixed with the uracils according to the invention in a ratio of 1: 4 to 4: 1, a ratio of 1: 2 to 2: 1 being given before.



   Phenols
Dinitro-sec-butylphenol and its salts, pentachlorophenol and its salts.



   These phenols can be mixed with the uracils according to the invention in a ratio of 1:10 to 20: 1, a ratio of 1: 5 to 5: 1 being preferred.



   Carboxylic acids and derivatives
The following carboxylic acids and derivatives can be mixed with the uracils according to the invention in the following proportions: A. 2,3,6-trichlorobenzoic acid and its salts,
2,3,5,6-tetrachlorobenzoic acid and its salts,
2-methoxy-3,5,6-trichlorobenzoic acid and its salts,
2-methoxy-3,6-dichlorobenzoic acid and its salts,
3-amino-2,5-dichlorobenzoic acid and its salts, 3-nitro-2, 5-dichlorobenzoic acid and its salts,
2-methyl-3, 6-dichlorobenzoic acid and its salts,
2, 4-dichlorophenoxyacetic acid and its salts and
Ester,
2,4,5-trichlorophenoxyacetic acid and its salts and esters, (2-methyl-4-chlorophenoxy) acetic acid and its
Salts and esters, 2- (2, 4, 5-trichlorophenoxy) propionic acid and their
Salts and esters,
2- (2, 4, 5-trichlorophenoxy) -ethyl-2, 2-dichloropropionate,

      4- (2, 4-dichlorophenoxy) butyric acid and its
Salts and esters, 4- (2-methyl-4-chlorophenoxy) butyric acid and its
Salts and esters,
2,3,6-trichlorobenzyloxypropanol.



   Mixing in a ratio of 1:16 to 8: 1, preferably 1: 4 to 4: 1.



  B. 2,6-dichlorobenzonitrile.



   Mixing in a ratio of 1: 4 to 4: 1, preferably 1: 3 to 3: 1.



  C. Trichloroacetic acid and its salts.



   Mixing in a ratio of 1: 2 to 25: 1, preferably 1: 1 to 8: 1.



  D. 2,2-dichloropropionic acid and its salts.



   Mixing in a ratio of 1: 4 to 8: 1, preferably 1: 2 to 4: 1.



  E. ethyl ester of N, N-di- (n-propyl) -thiolcarbamic acid, n-propyl ester of N, N-di- (n-propyte) -thiotcarbamic acid, ethyl ester of N-ethyl-N- (n- butyl) thiol carbamic acid, n-propyl ester of N-ethyl-N- (n-butyl) thiol carbamic acid.



   Mixing in a ratio of t: 2 to 24: 1, preferably 1: 1 to 12: 1.



  F. Isopropyl ester of N-phenylcarbamic acid, isopropyl ester of N-nyl) -carbamic acid, 4-chloro-2-butynyl ester of N- (m-chlorophenyl) carbamic acid.



   Mixture in a ratio of 1: 2 to 24: 1, preferably I: I to 12: 1.



  G. 2,3,6-Trichlorophenylacetic acid and its salts.



   Mixing in a ratio of 1:12 to 8: 1, preferably 1: 4 to 4: 1.



  H. 2-chloro-N, N'-diallylacetamide, maleic hydrazide.



   Mixing in a ratio of 1: 2 to 10: 1, preferably 1.1 to 5: 1.



   Inorganic and mixed inorganic-organic salts
The following salts can be mixed with the uracils in the following proportions: A. Calcium propyl arsonate, disodium monomethyl arsonate,
Octyldodecylammonium methyl arsonate, dimethyl arsenic acid.



   Mixing in a ratio of 1: 4 to 4: 1, preferably I: 2 to 2: 1.



  B. sodium arsenite.



   Mixing in a ratio of 1: 5 to 40: 1, preferably 1: 4 to 25: 1.



  C. Lead arsenate, calcium arsenate.



   Mixing in a ratio of 100: 1 to 600: 1, preferably 150: 1 to 400: 1.



  D. Sodium tetraborate, hydrated, granulated,
Sodium metaborate, sodium pentaborate,
Polyborchlorate, unrefined borate mineral, such as Borascu.



   Mixing in a ratio of 3: 1 to 1500: 1, preferably 6: 1 to 1000: 1.



  E. ammonium thiocyanate.



   Mixing in a ratio of 1:10 to 20: 1, preferably 1: 5 to 5: 1.



  F. Sodium Chlorate.



   Mixing in a ratio of 1: 1 to 40: 1, preferably 2: 1 to 20: 1.



  G. Ammonium sulfamate.



   Mixing in a ratio of 1: 1 to 100: 1, preferably 1: 1 to 50: 1.



   Other organic herbicides
These organic herbicides can be mixed with the uracils in the following proportions: A. 5,6-Dihydro- (4A, 6A) -dipyrido- (1,2-A, 2 ', 1'-C) pyrazinium dibromide,
Mixing in a ratio of I: 20 to 16: 1, preferably 1: 5 to 5: 1.



  B. 3-Amino-1,2,4-triazole.



   Mixing in a ratio of 1:20 to 20: 1, preferably 1: 5 to 5: 1.



  C. 3,6-endoxohexahydrophthalic acid.



   Mixing in a ratio of 1: 3 to 20: 1, preferably 1: 2 to 10: 1.



  D. Hexachloroacetone.



   Mixing in a ratio of 1: 2 to 16: 1, preferably 1: 1 to 8: 1.



  E. Diphenylacetonitrile,
N, N-dimethyl-a, a-diphenylacetamide,
N, N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniiline,
N, N-di-n-propyl-2,6-dinitro-4-methylaniline,
Mixing in a ratio of 1:10 to 30: 1, preferably 1: 5 to 20: 1.



  F. 0- (2,4-dichlorophenyl) -O-methyl-isopropyl-phosphoramidothiat,
Dimethyl ester of 2,3,5,6-tetrachloroterephthalic acid.



   Mixing in a ratio of 1: 4 to 20: 1, preferably 1: 3 to 15: 1.



  G. 2,4-Dichloro-4'-nitrodiphneyl ether.



   Mixing in a ratio of 1:10 to 30: 1, preferably 1: 5 to 20: 1.



   The following examples serve to further explain the invention, parts and ratios being based on weight, unless stated otherwise.



      Example I.
Production of 3-norbornylmethyl-5-chloro
6-methyluracil
8.0 parts of chlorine are stirred into a solution of 23.4 parts of 3-norbornylmethyl-6-methyluracil in 100 parts of glacial acetic acid, the temperature being kept below 30 ° C. during this addition. The solution is stirred for a further half an hour at room temperature and then poured into ice water, whereupon a solid separates out, which is filtered off and washed well with water, 21 parts of crude 3-norbornyl methyl-5-chloro-6-methyluracil being obtained.



   The following compounds according to the invention can be prepared as above by using, instead of the uracil and halogen, equivalent amounts of the substituted uracils and halogens according to the table below (in the case of iodine, an equivalent of fuming nitric acid is slowly added last to prevent iodination to complete).



     Starting uracil reactants Parts by weight of halogen Parts by weight of uracil product 3-norbornylmethyl-6-methyluracil 23,4 Br 17,0 3-norbornylmethyl-5-bromo-6-methyluracil
3-Cyclopropylmethyl-5-bromo-3-cyclopropylmethyl-6-methyluracil 18.0 Br 17.0 6-methyluracil 3- (1, 4, 5,6-tetrachlor-7, 7-dimethoxy-30, 5 Cl 8, 0 3- (1. 4 * 5, 6-tetrachloro-77-dimethoxy bicyclo- [2, 2.

   l] -hept-5-en-bicyclo- [2, 2, I] -hept-5-en-2-ylmethyl) - 2-ylmethyl) uracil 5-chloruracil 3-cyclohexylmethyl-6-methyluracil 22, 2 J 26.0 3-Cyclohexylmethyl-5-iodo-6-methyluracil 6-methyl-3- (cis + trans) -4-methyl-23.5 CI 8.0 5-chloro-6-methyl-3- (cis- r trans) - cyclohexylmethyluracil 4-methylcyclohexylmethyluracil 6-methyl-3- (cis-trans) -3-methy) -23, 5a8, 05-Chior-6-methy) -3- (cis trans) - cyclohexylmethyluracil 3-methylcyclohexylmethyluracil uracil Starting reactants Parts by weight of halogen Parts by weight of uracil product 6-methyl-3- (2-methyl-cyclohexyl-23.5 Cl 8,0 5-chloro-6-methyl-3- (2-methyl-cyclohexylmethyl) ) -uracil methyl) -uracil 3- (1-cyclohexylethyl) -6-methyl- 23.5 Cl 8.0 5-chloro-3- (1-cyclohexylethyl)

  uracil 6-methyluracil 3-cyclohexylmethyl-6-methyluracil 22, 1 Cl 8, 0 5-chloro-3-cyclohexylmethyl-
6-methyluracil 3- (2-cyclohexyl-ethyl-23.5 Cl 8, 0 5-chloro-3- (2-cyclohexylethyl) - 6-methyluracil 6-methyluracil 3-cyclohexylmethyluracil 20, 7 Cl 8.0 5-chloro -3-cyclohexylmethyluracil 3-cyclohexylmethyl-6-methyluracil 22.1 Br 17.0 5-bromo-3-cyclohexylmethyl
6-methyluracil 6-ethyl-3- (2-norbornylmethyl) - 24.8 Br 17.0 5-bromo-6-ethyl-3- (2-norbornyl-uracil methyl) -uracil 6-methyl-3 - [( 3-methylcyclohexyl) - 23.5 Br 17.0 5-bromo-6-methyl-3 - [(3-methylcyclo methyl] uraci.

   l hexyl) methyl] uracil 3- (1-cyclohexylethyl) -6-methyluracil 23.5 Br 17.0 5-bromo-3- (1-cyclohexylethyl)
6-methyluracil 6-methyl-3- [(4-methylcyclohexyl) - 23,5 Br 17,0 5-bromo-6-methyl-3- [(4-methylcyclo-methyl] -uracil hexyl) -methyl] -uracil 6-methyl-3- [(2-methylcyclohexyl) -23,5 Br 17,0 5-bromo-6-methyl-3 - [(2-methylcyclomethyl] uracil hexyl) methyl] uracil 3- [(4th Methoxycyclohexyl) methyl] -29.6 Br 17.0 5-Bromo-3 - [(4-methoxycyclohexyl) 6-methyluracil methyl] -6-methyluracil
The compounds of the above example can each be brought into preparation form as in Example 20 and used to control the weeds mentioned there.



   Example 2
Production of 3- (3-cyclohexen-1-yl-methyl) -
5-chloro-6-methyluracil
150 parts of sulfuryl chloride are stirred into a mixture of 218 parts of 3- (3-cyclohexen 1-yl-methyl) -6-methyluracil, 500 parts of glacial acetic acid and 82 parts of sodium acetate at 20 to 25 ° C. over the course of one hour. The mixture is stirred for a further hour, the reaction mixture is then evaporated and the resulting solid is recrystallized from an ethanol-water mixture, the 3- (3-cyclohexen-1-yl-methyl) -5-chloro-6-methyluracil being obtained.



   The following 5-chlorouracils are prepared in a similar manner by using the following uracil starting reaction instead of 3- (3-cyclohexen-l-yl-methyl) -6-methyluracils. Steiinehmer is used in the following amounts: uracil starting reaction participants parts by weight uracil product 3- (cyclohexylmethyl) -6-methyluracil 222 3- (3-cyclohexylmethyl) -5-chloro-6-methyluracil 3- (4-methoxy-3 -cyclohexen-1-methyl) - 251 3- (4-methoxy-3-cyclohexen-1-methyl) -5-chloro 6-methyluracil 6-methyluracil
The uracils of the above example can each be brought into preparation form as in Example 20 and used to control the weeds mentioned there.



   Example 3
Production of 3-l-methyl-1-cyclopentyl-l-ethyl) -
5-bromo-6-methyluracil
A solution of 243 parts of 3- (α-methyl-I-cyclopentyl-I-ethyl) -6-methyluracil in 700 parts of acetic acid, which contains 82 parts of sodium acetate, is treated with 160 parts of bromine and the mixture is evaporated after standing overnight. which contains some solid, under reduced pressure to a solid which is recrystallized from an ethanol-water mixture, the 3- (a-methyl-1-cyclopentyl-1-ethyl) -5-bromo-6-methyluracil receives.



   The following 5-bromouracils are prepared in a similar manner by using the following uracil starting reactants in the following amounts instead of the 3-methyl-1-cyclopentyl-1-ethyl) -6-methyluracils:

     Uracil starting reaction part by weight parts of uracil product 3- (bicyclo- [2,2,2] -oct-2-yl-methyl) - 262 3- (bicyclo- [2,2,2] -oct-2- yl-methyl) -5-bromo-6-methyluracil 6-methyluracil 3- (norborneny! methyl) -6-methyluracil 232 3- (norbornenylmethyl) -5-bromo-6-methyluracil
The uracils of the above example can each be prepared into wettable powder as in example 20 and used to control the weeds mentioned there in the vicinity of agricultural buildings.



   Example 4 Control of 3- [2-f5-indanyt) -ethyI] -5-fluoro-
6-methyluracil
A mixture of 38.0 parts of 2- (5 indanyl) ethyl urea, 29.4 parts of ethyl 2-fluoro-3-keto-butyrate, 0.5 part of 85% orthophosphoric acid and 200 parts of benzene is heated to reflux conditions . Water is collected in a Dean Stark trap.



  After 24 hours, 2.5 parts of water have collected and no further discharge of water appears to occur. The solution is now decanted, evaporated to a mixture of viscous oil and solid,
Urea reactant norbornylmethylurea
Norbornenylmethylurea
Cyclohexylmethyl urea
3-cyclohexene-1-methylurea
4-methoxy-3-cyclohexene-I-methylurea?

  -Methylcyclopenten-1-yl-1-ethylurea
Bicyclo- [2,2,2] -oct-2-yl-methylurea 2- (3a, 4/5 6,7, 7a-hexahydro-5-indanyl) ethylurea hexahydro-5-indanylmethylurea cyclohexenylethylurea (5, 6, 7,8,9,9, 9-hexachloro-1,2,3,4,4a, 5,8,8a octahydro-5, 8-methano-2-naphthylmethyl urea (cyclopropylmethyl) urea, cyclohexylethyl urea
Cyclobutyl methyl urea
The above uracils can be prepared as in Example 20 and used to control the weeds that grow around agricultural buildings.



   Example 5
Production of 3- (1, 4,5,6-tetrachlor
7,7-dimethoxy-bicyclo- [2,2,1] -hept-5-en-2-ylmethyl) -5-hydroxymethyl-6-methyluracil
A mixture of 208 parts by weight of 3- (1,4,5,6-tetrachloro-7,7-dimethoxy-bicyclo [2,2,1] -hept-5-en-2-ylmethyl) -6-methyluracil takes this in 200 parts of Athanot allf containing 10.6 parts of sodium methoxide and heated to reflux conditions for 10 minutes. Most of the ethanol is removed under reduced pressure and the residue is taken up in just enough water to dissolve. The pH value is lowered to 4 by adding concentrated hydrochloric acid.



  The resulting white solid is filtered off and recrystallized from an ethanol-water mixture, the pure 3- [2- (5-indanyl) ethyl] -5-fluoro-6-methyluracil being obtained.



   This compound can be formulated and used in a weed control agent as in Example 20, with similar results being obtained.



   The following uracils are prepared as in Example 4 by using equivalent urea reactants instead of 2- (5-indanyl) ethylurea:
5-fluorouracil product
5-norbornyl methyl-6-methylu racil
3-norbornenylmethyl-6-methyluracil
3-cyclohexylmethyl-6-methyluracil
3- (3-Cyclohexene-I-methyl) -6-methyluracil
3 (4-methoxy-3-cyclohexen-1-methyl)
6-methyluracil 3 - (?

  -Methyl-1-cyclopenten-1-yl-1-ethyl) - 6-methyluracil 3- (bicyclo- [2, 2, 2] -oct-2-yl-methyl) -
6-methyluracil 3- [2- (3a, 5,6,7,7a-hexahydro-5-indanyl) ethyl] -6-methyluracil
3gHexahydro-5-indanylmethyl) -6-methyluracil 3-cyclohexenylethyl-6-methyluracil 3- (5, 6,7,8,9,9-hexachloro-1,2,3,4,4a, 5,8,8aoctahydro- 5,8-methano-2-naphthylmethyl) 6-methyluracil
3- (Cyclopropylmethyl) -6-methyluracil
3-Cyclohexylethyl-6-methyluracil 3-Cyclabutylmethyl-6-me. thyluracil
1400 parts by weight of water, 31 5 parts by weight of ethyl alcohol, 60 parts by weight of Paraformaldehxd and 20 parts by weight of barium hydroxide Ge is heated until the components are completely dissolved.

   The solution is then cooled and the oil which precipitates is extracted with ether.



   Of the. Etherextract is dried with magnesium sulfate, filtered and concentrated under reduced pressure, whereby the 3- (1, 4,5,6-tetrachlor-7, 7-dimethoxy-bicyclo [2,2, 1] -hept-5-en- 2-yl-methyl) -5-hydroxymethyl
6-methyluracil receives.



   The following compounds are obtained as above by instead of the 3- (1, 4,5,6-tetrachloro-7,7 dimethoxy-bicyclo- [2, 2,1] -hept-5-en-2-yl- methyl-6-methyl uracil starting reactant 3-thylbicyclo- [2, 2,1] -oct-5-en-yl-methyl)
6-methyluracil 3- (hexahydro-5-indenylmethyl) -6-methyluracil 3- (5, 6,7,8,9,9-hexachloro-1,2,3,4,4a, 5,6,7,8 , 8a deca, hydro-5, 8-methanonaphth-2-ylmethyl) uracil 3- (4J-methoxy-3-cyclohexene-1-methyluracil
3-cyclohexylmethyl-6-methyluracil
The uracils of the above example can be prepared as in Example 20 and used to control the weeds that grow around agricultural buildings.



   Example 6
Preparation of the sodium salt of 3-cyclopropylmethyl-5-bromo-6-methyluracil
A solution of 4 parts of sodium hydroxide in
100 parts of water is treated with 25 parts of 3-cyclopropyl methyl-5-bromo-6-methyluracil while stirring and heating to effect solution. By removing the water from the solution under reduced pressure, the sodium salt of 3-cyclopropylmethyl 5-bromo-6-methyluracil remains as a white solid.



   Example 7
Preparation of the tetrabutylammonium salt of 3-cyclohexylmethyl-6-methyluracil
A mixture of 222 parts of 3-cyclohexylmethyl-6-methyluracil and 865.8 parts of a one molar solution of tetrabutylammonium hydroxide in methanol is stirred with gentle heating until a clear solution is obtained. The solution is stripped to dryness under reduced pressure and the resulting solid is recrystallized twice from 900 parts of ethyl acetate, whereby the pure tetrabutylammonium salt of 3-cyclohexylmethyl-6-methyluracil is obtained.



   The tetrabutylammonium salt of 3-norbornylmethyl-6-methyluracil can be obtained in a similar manner by reacting an appropriately substituted uracil with an appropriate quaternary ammonium hydroxide.



   The uracil salts of the present example can be brought into preparation form as in example 21 and used for weed control.



   Example 8
Preparation of 3-cyclopropylmethyl-5, 6-penta methylenuracil
A mixture of 115 parts by weight of 3-cyclopropylmethylurea, 202 parts by weight of ethyl-2-cycloheptanone-1-carboxylate, 40 parts by weight of phosphoric acid, 1000 parts by weight of dioxane and 879 parts by weight of benzene is stirred for 4 hours at reflux conditions, during which time the water released during the reaction with a uracils equivalent amounts of the following uracil starting reagents used.



   5-hydroxyalkyluracil product 3- (a-ethylrbicyclo- [2, 2,2] -oct-5-en-2-yl-methyl)
5-hydroxymethyl-6-methyluracil
3- (hexahydro-5-indenylmethyl) -5-hydroxy methyl-6-methyluracil
3- (5, 6,7,8,9,9-hexachloro-1,2,3,4.4a. 5,6,7,8,8a decahydro-5, 8-methanonaphth-2-ylmethyl) 5-hydroxymethyluracil
3- (4-methoxy-3-cyctohexen-1-methy!) -5-hydroxymethyluracil
3-cyclohexylmethyl-5-hydroxymethyl
6-methyluracil
Template is removed. The solvent is stripped off under reduced pressure and part of the solid is recrystallized from cyclohexane, whereby the ethyl 2- (3-cyclopropylureido) -1-cyclohepten-1-carboxylate is obtained.



   The remaining, non-recrystallized solid is dissolved in 2360 parts by weight of absolute alcohol containing 248 parts by weight of sodium methoxide, and
Refluxed for 10 minutes. The solvent is stripped off under reduced pressure and the residue is dissolved in water, cooled, acidified, the solid is filtered off, dried and recrystallized from ethanol, whereby 3-cyclopropylmethyl-5,6-pentamethyleneuracil is obtained.



   The preparation and use according to Example 23 are suitable for the uracils of the present example.



   Example 9
Production of 3- (4-methoxycyclohexylmethyl) -
5-methyluracil
A mixture of 70.8 parts of 1- (4-methoxycyclohexylmethyl) urea, 73 parts of diethyl 2-methyloxal acetate and 4 parts of 85% orthophosphoric acid in
400 parts of benzene are refluxed for 8 hours, during which time 7.8 parts of water collect. The solvent is removed, the residual oil is taken up in 400 parts of water, which contain 24 parts of sodium hydroxide, the solution is heated for 2 hours on a steam bath with movement, and the 6-carboxy-3- (4-meth-) is precipitated by acidification with concentrated hydrochloric acid. oxycyclohexyl) -5-methyluracil, this filtered off,

   dries in air and absorbs it as a suspension in 100 parts of a eutectic mixture of diphenyl ether and diphenyl. The resulting mixture is heated to reflux conditions with stirring, whereupon
Carbon dioxide evolved. When the evolution of carbon dioxide ceases, the mixture is cooled, filtered and the solvent washed out with benzene, the crystalline 3- (4-methoxycyclobexylmethyl) -5-methyluracil remaining behind.



   The following compounds are obtained as above by using, instead of the 1- (4-methoxycyclohexyl methyl) urea and diethyl 2-methyloxalacetate, equivalent amounts of monosubstituted ureas and thio ureas and equivalent amounts of oxaloacetates according to the following table.



  Oxaloacetate Parts by weight Urea Parts by weight Substituted producturacil Diethyl-2-methyl-73 1- (Decahydro-1, 3-5 * 8-88, 4 3- (Decahydro-1,4-5,8-dioxalacetate dimethanonaphth -2-yl) - methanonaphth-2-yl-methyl) urea 5-methyluracil diethyl-2-methyl-73 1- (norbornyl-methyl-67, 2 3- (norbornylmethyl) oxaloacetate urea 5-methyluracil diethyl-2-methyl -73 Cyclopropylmethyl-42 3-Cyclopropylmethyl-oxaloacetate urea 5-methyluracil Diethyl-2-methyl-73 Cyclohexylmethyl-58, 8 3-Cyclohexylmethyloxalacetat urea 5-methyluracil Diethyl-2-methyl-73 1- (4-Methylcyclohexyl-64.4 3- (4-methylcyclohexmethyl) oxaloacetate methyl) urea 5-methyluracil diethyl-2-methyl-73 (hexahydroindan-5-yl 78,

   5 3- (hexahydroindan-5-ylmethyl) oxal acetate methyl-urea 5-methy luracil diethyl-2-methyl-73 4-bromocyclohexylmethyl-94. 0 3- (4-bromocyclohexylmethyl) - oxaloacetate methylurea 5-methyluracil diethyloxalacetate 75.2 3- (3-cyclohexen-1-yl-61.6 3- (3-cyclohexen-1-methyl) methyl) -urea uracil diethyloxaloacetate 75 , 2 3- (4-methoxy-3-cyclo-73, 6 3- (4-methoxy-3-cyclohexene-hexene-1-methyl) -urea 1-methyl) -uracil
The uracils of the above example can be prepared as in Example 20 and used to control the same weeds.



   Example 10
Preparation of 3-norbornenylmethyl-5-cyanuracil
A mixture of 166 parts of norbornenylmethylurea, 66 parts of malononitrile and 444 parts of tri-ethyl-o-formate is heated to 70 to 100 ° C. for 3 hours with stirring. The volatile constituents are distilled off under reduced pressure and steam bath temperature. The resulting solid, [(3-norbornenylmenthylureido) methylene] malononitrile, is purified by recrystallizing from a mixture of alcohol and water.



   242 parts of [(3-norbornenylmethylureido) methylene] malononitrile, 54 parts of sodium methoxide and 1000 parts of methanol are stirred while protecting from atmospheric moisture and the mixture is left to stand for 5 days at room temperature. The alcohol is distilled off under reduced pressure and the resulting solid is dissolved in 2000 parts of cold water. The solution is made slightly acidic by the gradual addition of acetic acid, the 3-norbornenylmethyl-5-cyancytosine which separates out is filtered off, washed with 1000 parts of cold water and dried.



   A solution of 242 parts of 3-norbornenylmethyl-5-cyancytosine in 1000 parts of 3N hydrochloric acid is refluxed for 3 hours and then cooled. The 3-norbornenylmethyl-5-cyanuracil which separates out is filtered off and recrystallized from a mixture of alcohol and water.



   The uracils according to example 10 can be prepared and used as in example 24.



   Example 11
Production of 3-norbornenylmethyl-5-methoxymethyluracil
500 parts of methanol, 10 parts of chloroacetic acid and 262 parts of 3-norbornenylmethyl-5-hydroxymethyluracil are introduced into a bomb and heated to 125 ° C. for 5 hours. The reaction mixture is then concentrated in 400 parts of acetonitrile to give an oil, briefly refluxed with 5 parts of activated charcoal (decolorizing charcoal), filtered hot and distilled under reduced pressure, giving the solvent-free 3-norborr, enylmethyl-5-methoxymethanoluracil.



   The uracil can be brought into preparation form as in Example 20 and used.



   3-Cyclohexylmethyl-5-methoxymethyl-6-methyluracil is prepared in a similar manner as above.



   Example 12
3- (4-chlorocyclohexylmethyl
5, 6-dichloruracil 25 on
Alkylnaphthalenesulfonic acid, sodium salt 1%
Lignosulfonic acid, Na salt 1% attapulgite clay 73 "
These ingredients are mixed and then placed on a grinder and ground wet and granulated. The granulate obtained is then dried and classified.



   In the same way the 3- (decahydro-1, 4,5, 8-dimethanonaphthylmethyl) -5-hyroxymethyl-6methyluracil can be prepared.



   With these agents, with application before emergence in a dosage of 12, 3 to
Fight 16.8 kg of active ingredient / ha of Bromus secali us and Avena fatua that grow on roadsides.



   Example 13 5-bromo-6-methyl-3- (2-norbornylmethyl) uracil (exo-endo mixture) 2 5 low viscosity methylcellulose 3%;
Kaolin clay 7 2
These ingredients are mixed and finely ground (mill of the Micropulverizer type), then ground on a heavy mixer with 16 to 20% water and extruded through a 3.57 mm nozzle opening (9, i'64) to form rods, which are in the cut into pieces of 3. 18 mm using a rotating knife. The pellets obtained are then dried.



   With 67.3 kg of this preparation per hectare, excellent control of Ambrosia artemisiifolia, wild Secale cereale, Brassica kaber, Plantago sp., Mollugo verticillata, Digitaria sp., Setaria sp., Xanthium sp. and Portulaca oleracea that grow around sign posts and telephone poles.



   Example 14 3- (4-Methoxycyclohex-3-enmethyl) -
5,6-dimethyluracil 80%
Dodecylbenzenesulfonic acid, Na salt 2% sodium! igninsulfonate i%
Attapufgite clay 17%
To produce a wettable powder, these ingredients are mixed on a ribbon blender, finely ground on a hammer mill until the size of essentially all particles is below 50 microns, and then mixed again until homogeneous.



   Example 15
3-cyclopropylmethyl-5-bromo
6-methyluracil 50.0%
Alkylnaphthalenesulfonic acid, sodium salt 1.0%
Na salt polymerized alkylnaphthalene sulfonic acid 0.5% calcined, non-squeezing clay des
Montmorillonite types (Pikes Peak clay) 48.5%
To produce a wettable powder, the ingredients are mixed on a ribbon mixer and then finely ground on a hammer mill. The ground product is treated on an air attrition mill until the particle size is substantially below 10 microns and then mixed again until homogeneous.



   Another active ingredient that can be prepared into wettable powders in the same way is 3-cyclo-butenylmethyl-5-bromo-6-methyluracil.



   Example 16
A wettable powder is prepared by mixing the following ingredients on a ribbon blender.



      3-Cyclohexylmethyl-5-chloro-6-methyluracil 50%
Kaolin Clay 46% Dioctyl Ester of Sodium Suosuccinic Acid% Sodium Hgnine Sulphonate 3%
The mixed mixture is ground on a hammer mill until the Teilcl. s are substantially finer than 50 microns and then mixed until homogeneous.



   Example 17 3- (4-methylcyclohexylmethyl) -5-bromo-
6-methyluracil 45.00%
Alkylnaphthalenesulfonic acid, Na salt 1.50% low-viscosity methylcellulose 0.25 0 synthetic calcium silicate 53.25%
These ingredients are mixed and micronized until the particle diameter is 50 microns or less. The mixture is then mixed again.



   Instead of 3- (4-methylcyclohexylmethyl) -5-bromo 6-methyluracils, equivalent amounts of 3- (4-propylcyclohexylmethyl) -5-bromo
6-methyluracil or
Use 6-methyl-3- (2-norbornylmethyl) thymine.



   Example 18
5-bromo-6-methy! -3- (2-norbornylmethyl) uracil (exo-endo mixture) 80, 0 ',; Dioctyl sodium sulfon succinate, compacted 85/15 with 1.0%
Sodium N-methyl-N-palmitoyl taurate 1.0% synthetic, fine calcium silicate 18.0%
These ingredients are mixed. finely milled until the uracil particles have a diameter of about
Shredded 10 microns, then mixed again.



   Before emergence, the preparation is applied at a dosage of 2.2 to 4.5 kg active ingredient / ha in 374 liters of water to newly tilled fields of cucumber, watermelon and cantaloupe.



   Excellent control of Digitaria sp., Setaria sp., Echinochloa crusgalli, Secale cereale, Amaranthus sp., Chenopodium album, Hibiscus trionum and Brassica kaber is obtained with these treatments.



   Example 19
Aqueous concentrate
The following, aqueous concentrate is prepared by dissolving or suspending the two solid constituents in water with agitation. The product can easily be diluted to the application concentration and applied by spraying.



   3-norbornylmethyl-6-methyluracil,
1/2 calcium salt 10 "
Sodium lauryl sulfate 1%
Water 89 (l,
When applied at a dosage of 22.4 kg active ingredient / ha, this concentrate is suitable for general control of annual and perennial weeds on industrial sites and railway gravel.



   Example 20
Usable powder
3 - (α-Ethylbicyclo- [2.2.2] -oct
5-enylmethyl) -6-methyluracil 50.00 "
Alkylnaphthalenesulfonic acid, Na salt 1.75% partially desulfonated sodium lignin sulfonate 1.00% calcined montmorillonite clay 47, 25X
The ingredients are mixed, finely ground until all of the particles are less than 50 microns in diameter, and then mixed again until homogeneous.



   If this preparation is applied at 6.8 kg active ingredient / ha in the vicinity of agricultural buildings, excellent control of Digitania sp., Setaria sp., Stellaria sp., Hibiscus trionum and Nepeta cataria is obtained.



   Excellent results are also obtained when the following compounds are prepared and used in the above manner: 3-norbornenylmethyl-6-methyl-2-thiouracil,
3-cyclopentenylmethyl-6-ethyluracil, 3- (4-methylcyclohexenylmethyl) -6-methyluracil, 3- (4-methyoxycyclohexylmethyl) -6-ethyluracil, 3- (4-bromocyclohexylmethyl) -6-methyluracil, 3- (1, 4 , 5,6-Tetrachlor-7,7-dimethoxybicyclo [2,2,1] -hept-5-en-2-ylmethyl) -6-methyluracil, 3- (hexahydroindan-5-ylmethyl) -6-methyluracil,
3- [2- (5-indanyl) ethyl] -6-methyluracil, 3- (cyclohexene-1-methyl) -6-methyl-2-thiouracil,
3- (3a, 4,5,6,7,7a-hexahydroinden-5-ylmethyl)
6-methyluracil.



   Example 21
Aqueous concentrate
An (aqueous concentrate is produced by dissolving the two solid components in water.



  The product can easily be diluted to application concentrations and applied by spraying
3-cyclobutylmethyl-5, 6-trimethyleneuracil,
Na salt 5%
Sodium lauryl sulfate 1%
Water 94%
This aqueous concentrate is applied with a hand pressure sprayer. With 3.4 kg active ingredient / ha in 374 l of water, an excellent pre-emergence control of Setaria sp., Echinochloa sp. and young sorghum halepense preserved in sugar cane.



   If the preparation is applied in a dosage of 22.4 kg of active ingredient in 935 l of water to the weeds that grow around bridge resistance, an excellent control of Hordeum leporinum, Galium, Convolvulus sepium, Daucus carota, Bromus secalinus, Xanthium sp. , Anthemis cotula and Pontentilla anserina.



   Example 22 Oil suspension 3-norbornylmethyl-5, 6-trimethylene
2-thiouracil 22%
Mixture of polyalcohol carboxylic acid residues and oil-soluble petroleum sulfonates 7%
Xylene 71%
The ingredients are mixed, micronized, and then sand-milled until the particles are 10 microns or less in diameter.



   If this preparation is diluted with weed control oil (Lion Herbicidal Oil No. 6) to a final concentration of 16.8 to 28.0 kg of active ingredient per 935 1 01, an excellent control against Digitaria sp., Bromus secalinus, wild Triticum vulgare and Avena sp. that grow on railway embankments.



   Example 23
Wettable powder
The following ingredients are mixed, then finely ground until the particle diameter is less than 50 microns, and mixed again:
3- (Cyclophentenylmethyl) -5,6-trimethyl uracil 25%
Alkylnaphthalenesulfonic acid, Na salt I% partially desulfonated sodium lignin sulfonate 1%
Attapulgite clay 73 0
This wettable powder will. suspended in water in a concentration of 16.8 to 22.4 kg of active ingredient per 935 1 of water and the suspension for combating Digitaria sp., Echinochloa crusgalli and Chenopodium album, which grow around telephone poles, in a dosage of 935 1 / ha applied by spraying.



   The following uracils can be prepared in a similar way and applied in 562 liters of weed control oil, with doses of 22.4 to 33.6 kg active ingredient / ha good weed control is obtained:
3- (2-methylcyclohexylmethyl) -5,6-trimethyleneuracil, 3- (4-methoxycyclohexylmethyl) -5,6-tetramethylene uracil,
3- (4-methylcyclohexenylmethyl) -5,6-trimethylene uracil.



   Example 24
Wettable powder 3- (norbornenylmethyl) -5, 6-trimethylene uracil 75.0% dioctyl sodium sulfone succinate 0.5%
Di-tert-acetylene glycol 0.5% coconut acid ester of sodium isethionate 0.5, precipitated sodium silicon dioxide aluminate 23.5;
These ingredients are mixed and finely ground until the diameter of the particles is less than 50 microns.



   If you use this preparation in a dosage of 28.0 kg of active ingredient per 748 liters of water, a fight against Bidens sp., Brassica kaber, Cheno podium a! bum, Piantago sp., Abutilon theophrasti medio, annual Poa. Poa compressa, Digitaria sp., Setaria sp. and young sorghum halepense growing in the vicinity of radar systems.



   The following compounds can be prepared in a similar way, but good weed control is obtained when used in the same way with equivalent dosages: 3- (1,4,5,6-tetrachloro-7,7-dimethoxybicclo [2 , 2, 1] -hept-5-en-2-ylmethyl) -5,6-trimethylene uracil, 3- 2 2] -oct-5-en-2-ylmethyl) -
5,6-trimethyleneuracil.



   Example 25
Pellets 3- (Decahydro-1. 4-5, (8-dimethano naphth-2-ylmethyl) -5, 6-trimethylene uracil 25 anhydrous sodium sulfate 10%
Sodium lignosulfonate 10%
Ca, Mg-Bentonite 9,;
The ingredients are mixed and finely ground, then moistened with 18 to 20 times water and pressed out through small nozzle openings. The extrusions are cut into small pellets in the raised state during molding, which are then dried.



   With these pellets, applied by hand in doses of 16, 8 to 33.6 kg active ingredient / ha, annual as well as perennial weeds can be combated that grow on protective roadsides and in the vicinity of bridges, wind fences and country road signs.



   Example 26
Oil suspension
An oil suspension is made with the following ingredients: 3- (4-Isopropylcyclohexylmethyl) -
5-bromouracil 15%
Diesel oil 80%
Polyoxyethylene sorbitan ester of mixed pine resin and fatty acids 5%
The ingredients are ground together on a ball or roller mill until the solids are finely dispersed in the oil and the average particle size of the active ingredient is less than 5 microns. This bisuspension is diluted with water to form an aqueous emulsion for application to plants.



   Using 3- (4-methylcyclohexylmethyl) -5-methyluracil, an oil suspension is prepared in a similar manner.



   The emulsifiable oils of this example are useful for weed control in railroad stations and in stockyards. If these agents are diluted with water at a dosage of 1497 l / ha and sprayed in a dosage of about 28 kg active ingredient / ha from a railway spray truck, vegetation in the manner of Agropyron repens, Digitaria sp., Young Sorghum halepense, young Cynodon dactylon, Bromus tectorum, Ambrosia artemisiifolia, Xanthum sp., Chenopodium album and Enigeron canadensis for a long time.



   If you use the same oil suspending agent in concentrations of 28.0 kg active ingredient / ha in 1403 l of water in a drainage ditch made up of a mixed population of annuals and perennials. is attacked by broad-leaved weeds and grass weeds, excellent vegetation control is also obtained. The trench remains guarded for a long time.



   Example 27
Pellets 3- (1,4,5,6-tetrachloro-7,7-dimethoxybicyclo [2,2,1] -hept-5-en-2-ylmethyl)
5-chloruracil 25.0% anhydrous sodium sulfate 10.0%
Alkylnaphthalenesulfonic acid, Na salt 1.0% non-swelling Ca, Mg bentonite 64.0% S.
These ingredients are prepared in the form of pellets by first mixing and finely grinding them on a hammer mill, then moistening them with 18-22% water and then pressing them through a nozzle with 3.18-mm holes. The extrusions are cut into 3.18 mm pieces at the die face and dried.



   Another compound which is similarly suitable for the preparation is 3- (decahydro-1,4-5,8 dimethanonaphth-2-ylmethyl) -5-merhyluracil.



   Each of the pellet preparations of this example can be used by hand in a dosage of 28.0 kg active ingredient / ha for combating annual and perennial weeds along protective borders, safety fences and country road signs and strips of grass.



   When applied from an airplane, the same agents provide effective control of willow and oak in doses of 13.5 to 20.2 kg active ingredient / ha.



   Example 28
Pellets 3- (5, 6,7,8,9,9-hexachloro-1,2,3,4,4a, 5,6,7,8,8a decahydro-5,8-methanonaphth 2-ylmethyl) -hydroxymethyluracil Ó low viscosity methyl cellulose 3 "
Kaolin clay 72%
These components are mixed and finely ground, then ground on a heavy mixer with 15 to 20% water and pressed out through 3. 18 mm nozzle holes. The extrudates are cut into 3.18 mm pieces and then dried.



   3- (4-Methoxy cyclohexylmethyl0-5-methoxyuracil and 3- [2- (4-bromocyclohexyl) ethyl] -5-nitrouracil can also be prepared in this way.



   If you use these agents in a dosage of 28.0 kg active ingredient / ha in 561 l of water, a control of Digitaria sp., Echinochloa cursgalli, Setaria sp., Amaranthus sp. and Chenopodium album, which grow along boardwalks.



   Example 29
Wettable powder 3-norbornenylmethyl-5-hydroxymethyluracil 50.0% alkylnaphthalenesulfonic acid, Na salt 1.0r
Sodium salt of polymerized alkyl napthalenesulfonic acid 0.5 calcined, non-swelling clay des
Montmorillonite type (Pikes Peak clay) 48.5%
This wettable powder is made by mixing the ingredients on a ribbon blender and then finely grinding them on a hammer mill. The milled product is treated on an air abrasion mill until the particle size is less than 10 microns and then mixed again until homogeneous.



   Example 30
Emulsifiable 01
3- (4-Methoxy-3-cyclohexen-1-methyl) 5-iodine-1, 6-dimethyluracil 15 "mixed polyoxyethylene ethers and oil-soluble sulfonates 3%
Isophorone 40 50 alkylated naphthalene, mainly a-methylnaphthalene 42
These ingredients are mixed together to form a homogeneous solution.



   This preparation is suspended in a dosage of 28.0 to 33.6 kg of active ingredient in 561 liters of weed control oil and applied with a spray device along road embankments and under country road signs in a semi-arid area. The application takes place. when the weeds are 5 to 15 cm high, the growth of such difficult annual weeds as Digitaria sp., Setaria sp., creeping Polygonum aviculare, Mollugo verticillata and Portulaca oleracea is controlled.



   The 3- (4-methoxycyclohexyImethyl) -5-bromo-6-bromomethyl-1-methyluracil can be prepared in a similar manner, with similar results being obtained using equivalent amounts.



   Example 31
granules
3-cyclohexylmethyl-1, 6-dimethyluracil 10%
Kaolin clay 87% low viscosity methyl cellulose 3%
These components are mixed and finely ground, moistened with water, wet granulated and dried and classified to obtain granules with a grain size of 15 to 60 mesh.



   This preparation is applied in the vicinity of oil and gas sources in semi-arid areas before the rainy season.



   With 33.6 kg of active ingredient / ha, the preparation provides effective control of annual weeds such as Stellaria sp., Amaranthus sp., Brassica, Digitaria sp., Secale cereale and Setaria sp., In these areas.



   Example 32
Pellets 3- (1,4,5,6-tetrachloro-7,7-dimethoxybicyclo [2.2,1] -hept-5-en-ylmethyl) -5-bromo
1,6-dimethyluracil 10, 0 anhydrous sodium sulfate 10%
Sodium lignosulfonate 10%
Kaolin clay 35% non-swelling Ca, Mg bentonite 35%
These ingredients are mixed and finely ground, then moistened with 15 to 20% water and pressed out through 3.18-mm nozzle holes. The extrudates are cut into 3.18-mm pieces and dried to solid pellets.



   These pellets are applied along firebreaks at a dosage of 224 to 448 kg / ha. If this treatment is carried out before emergence or before the weeds reach a height of 71/9 to 10 cm, weeds such as young Festuca sp., Amaranthus sp., Chenopodium album, Ambrosia artemisüfolia, Brassica, annual Secale cereale, Stellana sp. and Digitaria sp. fights.



   The following uracils can be prepared as in Examples 33 and 35 and provide good weed control in equivalent amounts:
3-cyclopropylmethyl-5-methylthiol-6-methyl-
1- (m-methylthylphenylthio) uracil,
3- (4-methylcyclohexylmethyl) -6-propoxy
5-bromo-1-methyluracil,
3- (4-isopropylcyclohexylmethyl) -1, 5,6-trimethyl uracil, 3- (decahydro-1, 4-5, 8-dimethanonaphth-2-ylmethyl)
5-bromo-6-methyl-1- (trichloromethylthio) uracil.

 

Claims (1)

PATENT CLAIM Weed control agents, characterized in that they contain at least one compound of the formula EMI13.1 wherein R, cycloalkylalkyl with 4 to 13 carbon atoms, cycloalkenylalkyl with 5 to 13 carbon atoms, (substit. Cycloaikyl) -alkyl with a total of 5 to 14 carbon atoms or (substit. Cycloalkenyl) alkyl with a total of 5 to 14 carbon atoms, Ro denotes hydrogen, chlorine, fluorine, bromine, iodine, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, nitro, alkoxymethyl with 2 to 6 carbon atoms, hydroxyalkyl with 1 to 6 carbon atoms, alkenyl with 3 to 6 carbon atoms, thiocyanate, cyano, mercaptomethyl, methylthiomethyl, phenylthiomethyl, alkylthio with 1 to 4 carbon atoms, bromomethyl, fluoromethyl, chloromethyl or carboxymethylthio methyl, Rg hydrogen, chlorine, bromine, alkyl with 1 to 5 Carbon atoms, chloroalkyl with 1 to 4 carbon atoms, Bromoalkyl with 1 to 4 carbon atoms or alkoxy with 1 to 5 carbon atoms, R4 hydrogen, alkyl which is optionally substituted and has a total of 1 to 5 carbon atoms, alkenyl with 2 to 5 carbon atoms, alkynyl with 3 to 5 carbon atoms, acyl which is optionally substituted and has a total of 1 to 10 carbon atoms, carbamyl, which is optionally substituted and has a total of 1 to 7 carbon atoms, thiocarbamyl, which is optionally substituted and has a total of 1 to 7 carbon atoms, dialkylthionophosphoryl having 2 to 6 carbon atoms, Dialkylphosphoryl with 2 to 6 carbon atoms, alkylthio, which is optionally substituted and has a total of 1 to 12 carbon atoms, phenylthio, which is optionally substituted and has a total of 6 to 10 carbon atoms, benzylthio, which is optionally substituted and has a total of 7 to 12 carbon atoms, or Glycosyl and X denotes oxygen or sulfur, with the proviso that R and R; together can form a divalent alkylene bridge of the formula (CH.) n, in which n is 3, 4 or 5, or a salt thereof as active ingredient.