IL33885A - Pyrimidine derivatives,their preparation and herbicidal compositions containing them - Google Patents

Pyrimidine derivatives,their preparation and herbicidal compositions containing them

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Publication number
IL33885A
IL33885A IL33885A IL3388570A IL33885A IL 33885 A IL33885 A IL 33885A IL 33885 A IL33885 A IL 33885A IL 3388570 A IL3388570 A IL 3388570A IL 33885 A IL33885 A IL 33885A
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Israel
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formula
chloro
amino
pyrimidine
compounds
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IL33885A
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IL33885A0 (en
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Sandoz Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms

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

Description

¾rrimidine derivatives, their preparation and herbicidal compositions containing them SAHDOZ A.G. - la - 35885/2 The present Invention relates to pyrimidine derivatives.
This invention ooneems herbioldally aotive compounds of formula I, NH-R in which R signifies an alkyl radioal of 2 to 6 carbon atoms, an alkenyl radioal of 5 to 6 oarbon atoms* or a cycloalkyl radical, and X signifies a hydrogen or halogen atom, preferably a chlorine atom.
The invention provides processes for the production of compounds of formula I, characterized by a) reaoting a oompound of formula II, In which R mid X lmvo Uto above significance, with ammonia, or produoing a oompound of formula lb, in which X' signifies a halogen atom, and has the above significance, by halOKoimtlng n oompound of formula la 58852 in which R has the above significance, The compounds of formula lb stated above are novel and as such also form part of the present invention.
Process a) may for example be effected with a concentrated aqueous ammonia solution, and suitably in a water'*-misoible organic solvent which is inert under the reaction conditions, e.g. an alcohol. The process is suitably effected at a temperature of from 100° to l80°C, preferably 120° to 160°C. The process may desirably be carried out in a pressure vessel.
Process b) may be effected in conventional manner.
The compounds of formula la employed as starting . materials in process b) above may be produced by reacting a compound of formula III with an amine of formula IV, IV in whioh R. has the above significance^ - This reaction may be effeoted in conventional manner, for example in an organio solvent which is inert under the reaction conditions, e.g. an aloohol, and at the reflux temperature of the reaotion mixture. Suitably, the compounds of formula III and IV may be employed in a molar ratio of 1.2 . „ Process o)—may be affected in oonventional manner.
The resulting compounds of formula I may be isolated and purified in conventional manner. Where required, free base forms of the compounds of formula I may be converted to acid addition salt forms in conventional manner, and, likewise, vice versa.
The compounds of formula II employed as starting materials in process c) may be produced by reacting a compound of formula V, CI in which X has the above significance, with a compound of formula IV stated above.
The process may be effected in conventional manner, for example in an organic solvent which is inert under the reaction conditions. It is suitably effected at room temperature or slightly elevated temperature and the reaction time may typically vary from 1/2 to 2 hours. This process may lead to a mixture of the desired compounds of formula II and other aminated pyrimidines. The compounds of formula II may then be isolated, for example by steam distillation.
The compounds of formulae III, IV and V are either known or may be produced in manner known per se.
The compounds of formula I have herbicidal activity against the growth of undesired plants, commonly known as weeds, in particular against dicotyledonous weeds, e.g. Plantago lanceolata, Amaranthus retroflexus, Capsella bursa-pastoris, Chenopodium album, Galium aparine, Stellaria media and Senecio vulgaris, as well as against undesired grasses, for example Echinochloa crus-galli, Alo ecurus ratensis and Setaria s . - 4 - 13 -3048 The compounds furthermore exhibit a selective killing of weeds amidst cultivated plants. Thus, for example, maize, wheat, potatoes, onions and leeks, inter alia, are not signi icantly damaged by the use of the herbicides of the invention, especially when the herbicides are used after emergence of the cultured plants and the weeds. The herbicides are, however, efficient when used pre- or post-emergence of the cultivated plants and the weeds. The compounds of formula I are therefore indicated for use as herbicides.
An indicated suitable dosage of the herbicides of the invention is from 1 to 12 kg, preferably 2 to 6 kg per hectare.
For use as herbicides, the compounds of formula I may be formulated into suitable compositions, e.g. suspensions, emulsions, pastes and granules. The herbicidal compositions may be produced, for example, by intimately mixing or grinding the compounds of formula I with a suitable carrier, optionally with the addition of dispersing agents or a solvent which is inert to the active agent.
In order to produce compositions which can be applied in solid forms, e.g. dusting agents, strewing agents and granulates, the active agent may be mixed with a solid carrier, e.g. kaolin, talc, chalk and limestone.
Substances improving adhesiveness and/or giving a better wettability or dispersibility may also be incorporated into the composition.
Spraying powders may be obtained by mixing and grinding the active agents with a powdery carrier material until the mixture is homogeneous. The powdery carrier may for example be kaolin, talc, chalk, limestone and cellulose powder.
In order to produce solutions, one or more compounds of formula I are dissolved in an organic solvent, a solvent mixture or water. Examples of suitable organic solvents are ketones such as acetone, alcohols, hydrocarbons, chlorinated hydrocarbons and alkyl naphthalenes, alone or in admixture.
For special purposes, the compounds of formula I may be combined with other herbicides, e.g. of the urea class, saturated or unsaturated halogen fatty acids, halogen benzonitriles, halogen benzoic acids, phenoxy-alkyl carboxylic acids, carbamates and triazines.
Compositions containing compounds of formula I and suitable for application to a locus may contain for example 0.01 to 10 by weight of active ingredient. Concentrates may for example contain to 50 % by weight of active ingredient.
The herbicidal compositions can for example be applied as a spray or dust to the locus to be protected from the weeds. Such application can be made directly to the locus after emergence of the weeds, or alternatively the application can be made in advance of an anticipated emergence of weeds to prevent such.
The compounds of formula I may be used in free base form or in the form of acid addition salts, which salt forms have the same order of activity as the free base forms.
The broad disclosures of Italian Patent Specification No. 662, 501 and Swiss Patent Specification 3 4,259 encompass compounds of formula I. However, such specifications do not specifically disclose any of the compounds of formula I. Furthermore, the compounds of formula I show a considerably higher herbicidal effect and selectivity than the generality of the compounds of the said specifications. - 6 - ι -30 8 EXAMPI£_a: parts of 2-amino-4-isopropylamino-6-chloro-pyrimidine are mixed with 25 parts of isooctylphenyl decaglycol ether and 65 parts of acetone. The resulting emulsion is diluted with water to the desired concentration before use.
EXAMPLE b; parts of 2-amino-4-(2-methyl-ethylamino)-6-chloro-pyrimidine hydrochloride are mixed with parts of a condensation product of formaldehyde and naphthalene sulphonate, 2 parts of alk lbenzene sulphonate, 5 parts of dextrin, 1 part of ammonium caseinate and 62 parts of diatomaceous earth until a homogeneous mixture results and this is subsequently ground until the particles are considerably smaller than microns. This formulation is diluted with water to the desired concentration before use.
The outstanding effect of the agents of the invention is illustrated by the herbicidal effect of the compounds of general formula I and their salts indicated in the following Table. The evaluations indicated in the Table by figures 1 to 9 signify: 1 = no destruction, 9 = total destruction, whereas the intermediate values given refer to further graduations between the figures on the evaluation scale.
The following Table shows the effect of post-emergence treatment with 5 k of active agent per hectare.
The Table shows the excellent herbicidal effect of the agents of the invention and also their outstanding selectivity in culturing plants, e.g. maize.
Amaran- Capsel- Cheno- Gal Active ingredient of the thus la burpodium ap herbicide retro- sa-pa- album ne flexus storis 2-a mlnc-4-isopropylamino-6-chloro-pyrirnidine 9 9 9 2-amino- -isopropylamino-6-chloro-pyrimidine hydrochloride . 9 9 9 2-a mino- -isoproDylamino-6-chloro-py imidine trichloroacetate 9 9 9 2-amino-4-propylamino-6-chloro-pyrimidine 9 9 9 2-amino- -all 1amino-6-chloro-py imidine 9 7 8 2-amino-4-isobutylamino-6-chloro-py imidine 9 9 9 2-¾-iino-4-pentylamino-6-chloro-pyrimidine 9 9 6 2-a.mino-4-cyclohexylamino-6-chloro-pyrimidine 9 9 6 Amaran- Capsel- Cheno- Ga Active ingredient of the thus la bur- podium ap herbicide . retro- sa-pa- album ne lexus storis -amino-ii-n-butylamino-6-chloro-pyrimidine 9 9 8 2-a mino-4- n-hexylamino-6-chloro-py imidine 9 9 9 - amino- - sec-butylamino-6-chloro-pyrimidine 9 9 9 - 9 - 15 -3θ4δ The following Examples illustrate the production of the new compounds. The temperatures are indicated in degrees Centigrade.
EXAMPLE 1 ; 2-Amino-4-isopropylamino-6-chloro-pyrimidine . 400 g (2,l8 mols) of 2,4,6-trichloro-pyrimidine are dissolved in 2000 cc of alcohol. 280 g (4.75 mols) of isopropyl amine in 200 cc of alcohol are added to the solution while stirring and cooling, whereby the temperature should not exceed 50°. The mixture is subsequently stirred at room temperature for a further 60 minutes and the alcohol is then removed by evaporation in a water jet vacuum until the mixture hardens to a solid mass. The solid residue is washed with water and subjected to steam distillation. This distillation is continued until only traces of the steam-volatile 2-isopropylamino-4,6-dichloro-pyrimidine are deposited in the receiver. The steam-nonvolatile 4-isopropylamino-2,6-dichloro-pyrimidine is obtained. After distillation in a vacuum (B.P. 124°/0.1 mm of Hg) the pure product, having a M.P. of 69-70° after recrystallization from water/alcohol, is obtained. g (0.15 mols) of 4-isopropylamino-2,6-dichloro-pyrimidine in 100 cc of alcohol are mixed with 50 cc of a 23 % aqueous ammonia solution and the mixture is heated to 140° in an autoclave for 4 hours. The reaction mixture is subsequently evaporated to dryness in a vacuum, the solid residue is taken up in 300 cc of chloroform and washed thrice with 200 cc amounts of water. After drying with aluminium oxide and removing the chloroform by evaporation a viscous oil is obtained which solidifies slowly. The resulting 2-amlno-4-isopropylamino-6-chloro-pyrimidine has a M.P. of 114-116° after recrystallization from benzene/petroleum ether.
Analysis: C H CIN Molecular weight: l86.7 EXAMPLE 2 ; 2-Amlno- - isopropylamlno-6-Ghloro-pyrimidlne . 600 g of 2-amino-4,6-dichloro-pyrimidine ( 3 -66 mols) are added to JOQO cc of alcohol, 395 g of isopropylamine (8.05 mols) are added, and the mixture is slowly heated to 80° during the course of 2 hours while stirring. After the material is dissolved, the solution is heated under reflux for 3 hours. The alcohol is then distilled off and the residue dissolved in dilute sulphuric acid. The solution must give a clearly acid reaction. The solution is shaken out several times with chloroform. A layer of 3000 cc of chloroform is subsequently placed under the aqueous solution and the solution is made alkaline with a caustic soda solution (pH 11) , whereby the temperature should not exceed 35° · After shaking out the chloroform phase is separated and the aqueous phase is again shaken out with chloroform. The combined chloroform solution is dried with Glauber's salt after washing with water and the chloroform is evaporated. After standing for a short time the oily residue crystallizes. The product may be re-crystallized as described in Example 1 for purposes of purification.
EXAMPLE 3 ? 2-Amino- -isopropylaroino-5,6-dichloro-pyrimidine. g (0.1 mol) of 2-amino- -isopropylamino-6-chloro-pyrimidine in 250 cc of carbon tetrachloride are heated to reflux temperature while stirring. As soon as a clear solution results, chlorine is slowly passed through the solution until the taking up of chlorine stops. After about 90 minutes the solution is cooled, the precipitated material is filtered with suction and washed with carbon tetrachloride. The product may be recrystallized from dioxane.
M.P. 193° (decomp.). - 11 - 150-3048 Analysis: Molecular weight: 221 Calc: C 38.0 H 4.6 CI 32.1 N 25 - 3 % Pound: 38. 4.8 31.7 25.1 % The following compounds may be obtained in a manner analogous to that described in Examples 1 and 2: Example Molecular No. Formula weight 4 2-a.mino-4-n-hexylamino- C10H17C1N 228,7 6-chloro-pyrimidine 2x.amino-4-cyclohexylami.no- 225,7 C10H15C1¾ 6-chloro-pyrimidine 6 2-amino-4-sec_-butylamino- ¾H15C1 200,7 6-chloro-pyrimidine 7 2-amino-4-isobutylamino- 6-chloro-pyrimidine C8H13C1N4 200,7 8 2 -amino-4-n-pentylamino- C H15C1 214,7 6-chloro-pyrimidine 9 2-amino-4-tert-butvlamino- 200,7 6-chloro-pyrimidine The salts of the compounds of general formula I, which are also claimed as active in redients for the herbicides of zhe invention, may be produced in the usual manner, e.g.: Trichloroacetate of 2-amino- -isopropylamino-6-chloro-pyrimidine . 18.6 g (0.1 mol) of 2-amino-4-isopropylarnino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol and 18 g (0.11 mols) of trichloroacetic acid are added while cooling. The mixture is evaporated to dryness in a vacuum and the resulting solid, colourless residue is recrystallized from alcohol. The trichloroacetate has a melting point of I5O-I520 .
Analysis: C^H^CIN^.HO^CI, Molecular weight: 350 Calculated: C 30.9 H 3.5 CI 0.5 N l6.0 Found: 31.O 3.5 39-6 16.6 Hydrochloride of 2-an.ino- -isopropylamino-6-chloro-pyrimidine .
I8.6 g (0.1 mol) of 2-amino~4-isopropylamino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol and 11 g (0.11 mols) of 36^ hydrochloric acid are added while cooling. The mixture is evaporated to dryness in a vacuum and the resulting solid, colourless residue is recrystallized from alcohol. The hydrochloride has a melting point of 235-2360 .
Analysis: C^H^CIN^.HCI Molecular weight: 223 Calculated: C 37-7 H 5. CI 31.7 N 25.0 Found: 37.7 5. h 31.8 25.1 $ - 3A - 150-30 8 Methanesulphonate of 2-arnino-4-sec .butylamino-6-chloro-pyrimidine . .0 g ( 0.1 mol) of 2-amino-4-sec .butylamino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol and 10.5 S ( 0. 11 mols) of methanesulphonate are added to the solution with cooling. The mixture is evaporated to dryness in a vacuum. The resulting solid, very hygroscopic, colourless residue has a M.P. of 116-118° .
Analysis: .CH SO H Molecular weight: 296.5 Calc: C 36.5 H 5 - 7 CI 11.9 N 18.9 S 10.8$ Found: 36.8 5 -4 12.0 19- 3 10.3 % Hydrogen sulphate of 2-amino-4-secbutylamino-6-chloro-pyrimidine. .0 g ( 0.1 mol) of 2-amino-4-sec .butylamino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol and 10.8 g ( 0.11 mols) of sulphuric acid are added to the solution with cooling. The mixture is evaporated to dryness in a vacuum. The resulting solid, very hygroscopic, colourless residue has a M.P. of 95-105° · Analysis: Molecular weight: 298.5 Calc: C 32.9 H 5 - 0 CI 11.9 N 18.8 S 10.7 % Found: 3 .5 4.8 12.0 19- 0 10.7 % Phosphate of 2-amino-4-secbutylamino-6-chloro-pyrimidine. .0 g (0.1 mol) of 2-amino-4-sec .butylamino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol and 10.8 g ( 0.11 mols) of phosphoric acid are added to the solution with cooling. The mixture is evaporated to dryness in a vacuum and the resulting solid, colourless residue is recrystallized from alcohol or acetonitrlle .
M.P. 176° .
Analysis: Molecular weight: 298.5 Calc: C 32.9 H 5 - 3 CI 11.9 N 18.8 P 10.4 % Found: 32.1 5.2 11.8 18.2 10.4 % - 15 - 13&-3048 Hydrochloride of 2-amino-4-lsobutylan)ino-6-chloro-pyrimidine.
.C g (0.1 mol) of 2-amino-4-isobutylamino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol arid 11 g (0.11 mols) of 50. % hydrochloric acid are added to the solution with cooling. The mixture is evaporated to dryness in a vacuum and the resulting solid, colourless residue is recrystallized from alcohol or acetonitrile. M.P. 24l° .
Analysis: CgH^ClN^.HCl Molecular weight: 237 Calc: C 40-5 H 5 -9 CI 30.0 N 23.6 % Found: 40.7 6.3 29.8 23-0 % Trichloroacetate of 2-amino-4-isobutylamino-6-chloro-pyrimidine. .0 g (0.1 mol) of 2-amino- -isobutylamino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol and l8 g (0.11 mols) of trichloroacetic acid are added to the solution with cooling. The mixture is evaporated to dryness in a vacuum and the resulting solid, colourless residue is recrystallized from alcohol or acetonitrile. M.P. 149°.
Analysis: Molecular weight: 36 Calc: C 33-0 H 3.8 CI 39-0 N 15. % Found: 35.1 4.1 39-0 15.1 % Trichloroacetate of 2-amino-4-n-butylamino-6-chloro-pyrimidine , . G g ( 0.1 mol) of 2-amino-4-n-butylamino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol and 18 g ( 0.11 mols) of trichloroacetic acid are added to the solution with cooling. The mixture is evaporated to dryness in a vacuum and the resulting solid, colourless residue is recrystallized from alcohol or acetonitrile. M.P. 137° · Analysis: Molecular weight: 364 Calc: C 33 -0 H 3.8 CI 39.0 N 15.4 % Pound: 33.0 3.8 39.0 15.4 % Hydrobromide of 2-amino-4-n-butylamino-6-chloro-pyrimidine. .0 g ( 0.1 mol) of 2-amino-4-n-butylamino-6-chloro-pyrimidine are dissolved in 100 cc of alcohol and 14.1 g (0.11 mols) of 63 % hydrobromic acid are added to the solution with cooling. The mixture is evaporated to dryness in a vacuum and the resulting solid, colourless residue is recrystallized from alcohol or acetonitrile. M.P. 233° .
Analysis: CgH ClN^.HBr Molecular weight: 281.5 Calc: C 3 .2 H 5.0 N 19·9 % Found: 3^-5 .9 19- 1 % -17- 33885/2

Claims (17)

1. A process for the production of a compound of formula I, in which B.^ signifies an alkyl radical of 2 to 6 carbon atoms, an alkenyl radical of 3 to 6 carbon atoms, or a cycloalkyl radical* and X signifies a hydrogen or halogen atom, characterized by a) reacting a compound of formula II, NH-R in which R and X have the above significance, with ammonia, or t 33885/4 - 18 - b) producing a compound of formula lb, H-R. in which X' signifies a halogen atom, and has the above significance, by halogenating a compound of formula la: in which has the above signif cance.
2. A process for the production of compounds of formula I in Claim 1, substantially as herein described with reference to any one of the Examples,
3. Compounds of formula I in Claim 1, whenever produced by a process according to Claim 1 or 2*
4. * Compounds of formula I in Claim 1, in which either X. ie halogen and is as defined in Claim 1, or i is hydrogen and is isopropyl, isobutyl, sec.butyl, tert*butyl, n-pentyl, n-hexyl or cyclohezyl. i - 19 - 150-3048
5. 2-Amino-4-isoprcpylamino-6-chloro-pyrimidine.
6. 2-Amino-4-isopropylamino-5,6-dichloro-pyrimidine.
7. · 2-Amino-4-n-hexylamino-6-chloro-pyrimidine .
8. 2-Amino-4-cyclohexylamino-6-chloro-pyrlmidine .
9. 2-Amino-4-sec.butylamlno-6-chloro-pyrimldlne
10. 2-Amino-4-isobutylamlno-6-chloro-pyrlmidine
11. 2-Amino-4-n-pentylamino-6-chloro-pyrlmidine .
12. 2-Amino-4-tert.butylamino-6-chloro-pyrimidine.
13. A compound according to any one of Claims 4 to 12 in the form of an acid addition salt.
14. A herbicidal composition comprising a compound of formula I, stated in Claim 1, in free base or acid addition salt form, in association with a carrier or diluent.
15. A herbicidal composition according to Claim 14, substantially as herein described.
16. A method of combatting weeds in a locus, which comprises treating the locus with a compound of formula I, stated in Claim 1, in free base or acid addition salt form.
17. A method according to Claim l6, in which 1 to 12 kg
IL33885A 1969-02-14 1970-02-12 Pyrimidine derivatives,their preparation and herbicidal compositions containing them IL33885A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH223469A CH512187A (en) 1969-02-14 1969-02-14 Herbicidal agent

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IL33885A0 IL33885A0 (en) 1970-04-20
IL33885A true IL33885A (en) 1973-03-30

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AT (1) AT301249B (en)
BE (1) BE745903A (en)
CH (1) CH512187A (en)
CS (1) CS180561B2 (en)
DE (2) DE2065629A1 (en)
DK (1) DK128975B (en)
FR (1) FR2031422B1 (en)
GB (1) GB1294198A (en)
IL (1) IL33885A (en)
NL (1) NL7001629A (en)
RO (1) RO57219A (en)
SU (1) SU518106A3 (en)
ZA (1) ZA70977B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4025515A (en) * 1969-02-14 1977-05-24 Sandoz Ltd. 6-Chloro-2,4-diaminopyrimidines
FR2311776A1 (en) * 1975-05-23 1976-12-17 Sogeras 2,4-DIAMINO-5-CHLORO-6 PYRIMIDINES AND PROCESS FOR THEIR PREPARATION
NL7605319A (en) * 1975-05-23 1976-11-25 Mar Pha Etu Expl Marques PROCESS FOR PREPARING A MEDICINAL PRODUCT, SUCH MEDICINAL PRODUCT AND PROCESS FOR PREPARING SUITABLE MEDICINAL COMPOUNDS.
US4507146A (en) * 1982-12-28 1985-03-26 Ciba-Geigy Corporation 2,4-Diamino-6-halo-5-trifluoromethylpyrimidines having herbicidal activity
DE3601800A1 (en) * 1986-01-22 1987-07-23 Bayer Ag NEW 2,4-DIAMINO-6-HALOGENALKYLPYRIMIDINE
DE3808739A1 (en) * 1988-03-16 1989-09-28 Bayer Ag PYRIMIDINE DERIVATIVES
DE19917785A1 (en) * 1999-04-20 2000-10-26 Bayer Ag New 2,4-diamino-pyrimidine derivatives useful as microbicides in protection of plants and materials and as herbicides

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FR2031422B1 (en) 1973-03-16
FR2031422A1 (en) 1970-11-20
AT301249B (en) 1972-08-25
GB1294198A (en) 1972-10-25
DE2006145B2 (en) 1975-03-27
DK128975B (en) 1974-08-05
SU518106A3 (en) 1976-06-15
DE2065629A1 (en) 1974-10-24
BE745903A (en) 1970-08-12
ZA70977B (en) 1971-09-29
CH512187A (en) 1971-09-15
NL7001629A (en) 1970-08-18
DE2006145C3 (en) 1975-11-06
IL33885A0 (en) 1970-04-20
RO57219A (en) 1974-12-15
CS180561B2 (en) 1978-01-31
DK128975C (en) 1975-02-17
DE2006145A1 (en) 1970-10-29

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