LT3377B - Method of weed control - Google Patents

Method of weed control Download PDF

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LT3377B
LT3377B LTIP485A LTIP485A LT3377B LT 3377 B LT3377 B LT 3377B LT IP485 A LTIP485 A LT IP485A LT IP485 A LTIP485 A LT IP485A LT 3377 B LT3377 B LT 3377B
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Lithuania
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compound
methyl
mhz
cdc1
ethyl
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Jean Wenger
Paul Winternitz
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Ciba Geigy Ag
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Description

Išradimas skirtas augalų apsaugos cheminiams būdams, konkrečiai, kovos su piktžolėmis būdui, apdorojant augalus arba jų augimo vietas 3-(4-chlorfenil)-2,4diokso-1,2,3,4-tetrahidropirimidino dariniais.The present invention relates to chemical methods of plant protection, in particular to a method of controlling weeds by treating plants or their growing sites with 3- (4-chlorophenyl) -2,4-dioxo-1,2,3,4-tetrahydropyrimidine derivatives.

Yra žinomas kovos su nepageidautina augalija būdas (JAV patentas Nr. 3235363, kl. 71-2.5, publ. 1966), kuriameThere is a known method of combating unwanted vegetation (U.S. Patent No. 3,235,363, pp. 71-2.5, publ. 1966), in which

1,3-dipakeistų uracilų klasės junginiai ir jų kompozicijos yra taikomi kaip aktyvūs herbicidiniai ingredientai.The compounds of the 1,3-disubstituted uracil class and their compositions are applied as active herbicidal ingredients.

(kl. A01N 9/22, publ. kovos su piktžolėmis turintį 3Prancūzijos patente Nr. 7340682 1973) taip pat yra aprašomas būdas, kuriame herbicidu naudoja mišinį, cikloheksil-5,6-trimetilenuracilą bendros formulės(Cl. A01N 9/22, publ. 3, French Patent No. 7340682, 1973), also discloses a method of using a mixture of cyclohexyl-5,6-trimethylenuracil of general formula in a herbicide.

Šio išradimo tikslas yra padidinti budo efektyvumą.The object of the present invention is to increase the efficiency of the bud.

Tolimesni pavyzdžiai iliustruoja pateiktą būdą.The following examples illustrate the method presented.

kurioje Rx metilas, etilas, metoksikarbonilas,wherein R x is methyl, ethyl, methoxycarbonyl,

R2 - etilas, izopropilas arba n. butilas,R 2 is ethyl, isopropyl or n. butyl,

R3 - vandenilis arba fluoras,R 3 is hydrogen or fluorine,

R4 - metilas, etilas, n. propilas, monofluormetilas, trifluormetilas arba pentafluoretilas,R 4 - methyl, ethyl, n. propyl, monofluoromethyl, trifluoromethyl or pentafluoroethyl,

R5 - vandenilis, fluoras, chloras arba metilas, arba R4 ir R5 kartu sudaro triarba tetrametileną.R 5 is hydrogen, fluorine, chlorine or methyl, or R 4 and R 5 together form a tri-tetramethylene.

Į tirpalą, kuris paruošiamas 15,0 g 2-chlor-4-fluor-5(3, 6-dihidro-3,4-dimetil-2,β-diokso-l(2H)-pirimidinil)benzoinės rūgšties izopropilo esterio ištirpinant 100 ml acto rūgšties, kambario temperatūroje, maišant, per vieną minutę sulašinama 6,3 g sulforilchlorido. Dėl to temperatūra pakyla iki 30°C. Po to masė dar maišoma kambario temperatūroje ir po to išgarinama sausai pažemintame slėgyje. Liekana tirpinama etilacetate, po to gautas tirpalas praplaunamas paeiliui natrio bikarbonato vandeniniu tirpalu ir vandeniu. Organinė fazė išdžiovinama bevandeniu natrio sulfatu ir išgarinama sausai. Gautos nuosėdos perkristalinamos iš metilenchlorido ir dietilo eterio mišinio. Išdavoje gaunamas 2-chlor-4-fluor-5-(5-chlor-3,6-dihidro-3,4dimetil-2,6-diokso-l(2H)-pirimidinil)-benzoinės rūgšties izopropilo esteris, kurio lydymosi temperatūra 150-153°C (14 junginys).To a solution of 15.0 g of isopropyl ester of 2-chloro-4-fluoro-5- (3,6-dihydro-3,4-dimethyl-2, β-dioxo-1 (2H) -pyrimidinyl) benzoic acid of acetic acid, dropwise, 6.3 g of sulphonyl chloride per minute at room temperature with stirring. As a result, the temperature rises to 30 ° C. The mass is then stirred at room temperature and then evaporated to dryness under reduced pressure. The residue is dissolved in ethyl acetate, and the resulting solution is washed successively with aqueous sodium bicarbonate and water. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The resulting precipitate was recrystallized from a mixture of methylene chloride and diethyl ether. This yields the isopropyl ester of 2-chloro-4-fluoro-5- (5-chloro-3,6-dihydro-3,4-dimethyl-2,6-dioxo-1 (2H) -pyrimidinyl) -benzoic acid, m.p. -153 ° C (compound 14).

Analogiškai gaunami (1) junginiai, pateikti 1 lentelėje.Analogously, the compounds of (1) are shown in Table 1.

llentelė (1) formulės junginiaiTable II Compounds of formula (1)

Nfedžiagos, junginio Nr. Substances, compound no. Ri Ri r2 r 2 r3 r 3 r4 r 4 Rs Rs Lydymosi temperatūra, 0 Melting point, 0 1. 1. ch3 ch 3 CH(CH3)2 CH (CH 3 ) 2 F F -(CH2)3 - (CH 2 ) 3 - - 111-113 111-113 2. 2. 11 11th IV IV 11 11th -(CH2)4 - (CH 2 ) 4 - - 113-115 113-115 3. 3. II II c2h5 c 2 h 5 H H ch3 ch 3 H H 120-122 120-122 4 . 4. II II CH (CH3) 2 CH (CH 3 ) 2 F F 11 11th 11 11th - - 5. 5. 11 11th II II 11 11th 11 11th ch3 ch 3 119-120 119-120 6. 6th VI VI 11 11th VI VI II II F F 112-115 112-115 7 . 7th IV IV IV IV 11 11th nC3H7 nC 3 H 7 H H - - 8 . 8th II II 11 11th II II C2H5 C 2 H 5 - - - - 9. 9th II II 11 11th 11 11th 11 11th ch3 ch 3 - - 10. 10th H H II II II II CF3 CF 3 H H - - 11. 11th VI VI 11 11th II II 11 11th F F 66-68 66-68 12. 12th 11 11th 11 11th II II CH2FCH 2 F II II 85-89 85-89 13. 13th cooch3 cooch 3 11 11th 11 11th (CH2)3 (CH 2 ) 3 - - - - 14 . 14th ch3 ch 3 CH(CH3)2 CH (CH 3 ) 2 F F ch3 ch 3 CL CL 150-153 150-153 15. 15th IV IV 11 11th 11 11th c2f5 c 2 f 5 H H 78-81 78-81 16. 16th II II II II II II CF3 CF 3 CI CI - - 17. 17th 11 11th II II II II C2F5 C 2 F 5 F F - - 18. 18th II II 11 11th II II IV IV CI CI - - 19 19th VI VI II II H H cf3 cf 3 H H 104-107 104-107 20 . 20th II II c2h5 c 2 h 5 F F 11 11th II II 92-94 92-94 21. 21st II II nC4H9 nC 4 H 9 II II 11 11th 11 11th - - 22. 22nd C2Hs C 2 H s CH(CH3)2 CH (CH 3 ) 2 II II CH3 CH 3 II II 96-100 96-100 23. 23rd 11 11th IV IV II II CF3 CF 3 11 11th — - (1) junginių 1H (1) 1H of the compounds - BMR analizės duomenys: - NMR analysis data: junginys Nr. compound no. (CDC13, 60(CDCl 3 , 60 MHz) , MHz), δ, m.d. δ, m.d. : 7 : 7 ,88 (d, , 88 (d, 1Η) , 1Η), 7,38 (d, 1H) 7.38 (d, 1H) 5,77 (C, 1H), 5, 5.77 (C, 1H), 5, 30 (m, 1H), 30 (m, 1H), 3,50 (C, 3.50 (C, 3H) , 3H), 2,36 (C, 3H) 2.36 (C, 3H)

1,40 (d, 6H).1.40 (d, 6H).

Junginys Nr.7 (CDC13,Compound # 7 (CDC1 3 , 400 MHz), δ, m.d.: 7,88 400 MHz), δ, ppm: 7.88 (d, (d, (d, (d, 1H) , 6H) , 1H), 6H), 7,34 (d, 1,10 (t, 7.34 (d, 1.10 (t, 1H) , 2,53 (t, 3H) . 1H), 2.53 (t, 3H). 2H), 1,72 2H), 1.72 (m, 2H), (m, 2H), 1,36 1.36 Junginys The compound Nr.8 (CDC13,# 8 (CDC1 3 , 400 MHz), 400 MHz), δ, m.d.: δ, dd: 7, 84 7, 84 (d, (d, 1H) , 1H), 7,34 (d, 7.34 (d, 1H) , 5,75 (s, 1H), 5.75 (s, 1H), 5,25 1H), 5.25 (M, 1H), (M, 1H), 3,45 3.45 (s, (s, 3H) , 3H), 2,61 (m, 2.61 (m, 2H), 1,36 (d, 2H), 1.36 (d, 6H), 1,31 6H), 1.31 (t, 3H). (t, 3H). Junginys The compound Nr.9 (CDC13,# 9 (CDC1 3 , 400 MHz), 400 MHz), δ, m.d. : δ, m.d. : 7,82 7.82 (d, (d, 1H) , 1H), 7,33 (d, 7.33 (d, 1H), 5,23 (m, 1H), 5.23 (m, 1H), 3,51 1H), 3.51 (s, 3H), (s, 3H), 2,71 2.71 (m, (m, 2H) , 2H), 2,04 (s, 2.04 (s, 3H) , 1,35 (d, 3H), 1.35 (d, 6H), 1,28 6H), 1.28 (t, 3H) . (t, 3H). Junginys The compound Nr.10 (CDC13,# 10 (CDC1 3 , 400 MHz), 400 MHz), δ, m.d.: δ, dd: 7, 84 7, 84 (d, (d, 1H) , 1H), 7,37 (d, 7.37 (d, 1H), 6,38 (s, 1H), 6.38 (s, 1H), 5,25 1H), 5.25 (m, 1H), (m, 1H), 3, 57 3, 57 (d, (d, 3H) , 3H), 1,36 (d, 1.36 (d, 6H) . 6H). Junginys The compound Nr.13 (CDC13,No.13 (CDC1 3, 400 MHz), 400 MHz), δ, m.d.: δ, dd: 7, 84 7, 84 (d, (d, 1H) , 1H), 7,36 (d, 7.36 (d, 1H), 5,24 (m, 1H), 5.24 (m, 1H), 4,03 1H), 4.03 (s, 3H), (s, 3H), 3, 02 3, 02 (m, (m, 2H) , 2H), 2,79 (m, 2.79 (m, 2H) , 2,16 (m, 2H), 2.16 (m, 2H) , 1,36 2H), 1.36 (d, 6H) . (d, 6H). Junginys The compound Nr.16 (CDC13,No.16 (CDC1 3, 400 MHz) , 400 MHz), δ, m.d. : δ, m.d. : 7, 84 7, 84 (d, (d, 1H) , 1H), 7,39 (d, 7.39 (d, 1H), 5,25 (m, 1H), 5.25 (m, 1H), 3,62 1H), 3.62 (m, 3H), (m, 3H), 1,37 1.37 (d, (d, 6H) . 6H). Junginys The compound Nr.17 (CDC13,No.17 (CDC1 3, 400 MHz), 400 MHz), δ, m.d. : δ, m.d. : 7, 85 7, 85 (d, (d, 1H) , 1H), 7,39 (d, 7.39 (d, 1H), 5,25 (m, 1H), 5.25 (m, 1H), 3,60 1H), 3.60 (t, 3H), (t, 3H), 1,37 1.37 (d, (d, 6H) . 6H). Priedas. Appendix. Junginys The compound Nr.18 (CDC13,No.18 (CDC1 3, 400 MHz), 400 MHz), δ, m.d.: δ, dd: 7, 86 7, 86 (d, (d, 1H) , 1H), 7,39 (d, 7.39 (d, 1H), 5,25 (m, 1H), 5.25 (m, 1H), 3,60 1H), 3.60 (t, 3H), (t, 3H), 1, 37 1, 37 (d, (d, 6H) . 6H). Junginys The compound Nr.19 (CDC13,No.19 (CDC1 3, 200 MHz), 200 MHz), δ, m.d. : δ, m.d. : 7, 72 7, 72 (d, (d, 1H) , 1H), 7,59 (d, 7.59 (d, 1H), 7,27 (m, 1H), 7.27 (m, 1H) , 6,39 1H), 6.39 (s, 1H), (s, 1H), 5,26 5.26 (m, (m, 1H) , 1H), 3,56 (s, 3.56 (s, 3H) , 1,37 (d, 3H), 1.37 (d, 6H) . 6H). Junginys The compound Nr.20 (CDC13,# 20 (CDC1 3 , 400 MHz), 400 MHz), δ, m.d.: δ, dd: 7, 90 7, 90 (d, (d, 1H) , 1H), 7,39 (d, 7.39 (d, 1H) , 6,38 (s, 1H), 6.38 (s, 1H) , 3,57 1H), 3.57 (s, 3H), (s, 3H), 1,38 1.38 (t, (t, 3H) . 3H).

Junginys Nr.21 (DMCO, 400 MHz), 5, m.d.: 7,88 (d, 1H), 6,61 (s, 1H) , 4,30 (t, 2H) , Compound 21 (DMCO, 400 MHz), δ ppm: 7.88 (d, 1H), 6.61 (s, 1H), 4.30 (t, 2H), 8,05 3, 42 8.05 3, 42 (d, 1H), (c, 3H), (d, 1H), (c, 3H), 1,69 (m, 2H) , 1,39 (m, 1.69 (m, 2H), 1.39 (m, 2H), 0,92 2H), 0.92 (t, 3H). (t, 3H). Junginys Nr.22 (CDC13,Compound No.22 (CDC1 3 , 60 MHz), 60 MHz), δ, m.d. : δ, m.d. : 7, 92 7, 92 (d, 1H) , (d, 1H), 7,40 (d, 1H) , 5,76 (s, 7.40 (d, 1H), 5.76 (s, 1H), 5,28 1H), 5.28 (m, 1H), (m, 1H), 3, 98 3, 98 (m, 2H), (m, 2H), 2,35 (s, 3H), 1,34 (t, 2.35 (s, 3H), 1.34 (t, 9H) . 9H). 2 pavyzdys Example 2 Bandomosios piktžolių Pilot weed sėklos sėjamos į seeds are sown in sterilizuotą sterilized priemolio dirvožemį loam soil 0,5-2,0 0.5-2.0 cm gylyje· cm depth · Bandymas The test

vykdytas 7x7x7 cm dydžio plastmasiniuose puodeliuose. Kiekvieno iš tiriamų junginių naudojamas 1% acetoninis tirpalas, kuris prieš pat jo panaudojimą praskiedžiamas atitinkamu kiekiu vandentiekio vandens. Be to, prie kiekvienos kompozicijos pridedama 5 tūrinio procento jonilfenolio -(8) etoksilato.executed in 7x7x7 cm plastic cups. For each of the test compounds, use a 1% acetone solution which is diluted with an appropriate volume of tap water just before use. In addition, 5% v / v ionylphenol - (8) ethoxylate is added to each formulation.

Paskirstytos atskiruose puodeliuose sėklos apipurškiamos tiriamojo junginio tirpalu. Po to bandomos piktžolės kultivuojamos tamsiame šiltnamyje 17-19°C temperatūroje arba atitinkamai šiltnamyje su dirbtiniu apšvietimu 20-25°C temperatūroje, apšviečiant 16 valandų per parą. Santykinė oro drėgmė sudarė 40-90%. Po 4 savaičių nuo apipurškimo nustatytas kiekvieno tiriamo junginio herbicidinis efektyvumas, lyginant augalų, išaugančių iš apipurkštų sėklų, nekrozę (augimo vietų sumažėjimą) su nekroze augalų iš sėklų, kurios nebuvo apipurkštos tiriamu junginiu, o visi kiti darbai buvo atlikti vienodai. Rezultatai pateikti 2 lentelėje.Spray the seeds in separate cups with the test compound solution. The weeds to be tested are then cultivated in a dark greenhouse at 17 to 19 ° C or, respectively, in a greenhouse with artificial lighting at 20 to 25 ° C for 16 hours per day. Relative humidity was 40-90%. After 4 weeks of spraying, the herbicidal efficacy of each test compound was determined by comparing the necrosis (reduction in growth sites) of the plants grown from the sprayed seeds with those of the seeds not sprayed with the test compound, and all other work was done equally. The results are shown in Table 2.

lentelė (1) formulės junginių herbicidinis aktyvumasTable II Herbicidal activity of compounds of formula (1)

Junginio Dozė Galima šių piktžolių didelė nekrozė, %Compound Dose Potential for severe necrosis of these weeds,%

Nr. No. kg/ha kg / ha Avena Alopecarus fatua myosuroides Avena Alopecarus fatua myosuroides Sorgham halepense Sorgham halepense Stellaria media Stellaria media Spomoca purpur Spomoca purple 1. 1. 0,1 0.1 10 10th 40 40 20 20th 100 100 10 10th 0,3 0.3 30 30th 40 40 90 90 100 100 80 80 1,0 1.0 80 80 90 90 100 100 100 100 80 80 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 2. 2. 0.01 0.01 0 0 0 0 60 60 80 80 0 0 0,1 0.1 20 20th 50 50 70 70 100 100 0 0 0, 3 0, 3 90 90 100 100 100 100 100 100 40 40 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 3. 3. 0, 1 0, 1 10 10th 10 10th 0 0 10 10th 10 10th 0,3 0.3 10 10th 30 30th 10 10th 30 30th 20 20th 1,0 1.0 30 30th 30 30th 50 50 70 70 70 70 3, 0 3, 0 60 60 80 80 100 100 90 90 100 100 4 . 4. 0, 01 0, 01 10 10th 10 10th 10 10th 20 20th 10 10th 0,1 0.1 100 100 70 70 100 100 90 90 40 40 0,3 0.3 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 5. 5. 0, 1 0, 1 10 10th 40 40 90 90 10 10th 0 0 0,3 0.3 100 100 70 70 100 100 70 70 60 60 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3,0 3.0 100 100 100 100 100 100 100 100 100 100 6. 6th 0,01 0.01 0 0 0 0 0 0 30 30th 0 0 0, 1 0, 1 20 20th 50 50 100 100 100 100 50 50 0, 3 0, 3 100 100 100 100 100 100 100 100 70 70 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 7 . 7th 0, 1 0, 1 70 70 60 60 70 70 80 80 40 40 0, 3 0, 3 100 100 100 100 100 100 100 100 40 40 1, o 1, p 100 100 100 100 100 100 100 100 50 50

lentelės tęsinyscontinuation of the table

Junginio Dozė Galima šių piktžolių didelė nekrozė, %Compound Dose Potential for severe necrosis of these weeds,%

Nr. No. kg/ha kg / ha Avena fatua Avena fatua Alopecarus myosuroides Alopecarus myosuroides Sorgham halepense Sorgham halepense Stellaria media Stellaria media Spomoca purpur Spomoca purple 3,0 3.0 100 100 100 100 100 100 100 100 100 100 8 . 8th 0, 01 0, 01 0 0 0 0 20 20th 0 0 0 0 0,1 0.1 90 90 70 70 90 90 100 100 60 60 0, 3 0, 3 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 9. 9th 0, 01 0, 01 0 0 10 10th 70 70 20 20th 20 20th 0,1 0.1 60 60 90 90 100 100 100 100 70 70 0,3 0.3 100 100 100 100 100 100 100 100 70 70 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 10. 10th 0, 01 0, 01 100 100 100 100 100 100 100 100 100 100 0,1 0.1 100 100 100 100 100 100 100 100 100 100 0, 3 0, 3 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3,0 3.0 100 100 100 100 100 100 100 100 100 100 11. 11th 0,01 0.01 30 30th 30 30th 40 40 40 40 20 20th 0,1 0.1 100 100 100 100 100 100 100 100 100 100 0,3 0.3 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 12. 12th 0, 01 0, 01 10 10th 20 20th 70 70 40 40 30 30th 0,1 0.1 80 80 80 80 80 80 100 100 60 60 0,3 0.3 100 100 100 100 80 80 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 13. 13th 0,1 0.1 0 0 0 0 0 0 0 0 0 0 0, 3 0, 3 30 30th 20 20th 70 70 30 30th 20 20th 1,0 1.0 70 70 80 80 100 100 100 100 70 70 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 14 . 14th 0,1 0.1 30 30th 30 30th 60 60 20 20th 0 0 0,3 0.3 100 100 80 80 70 70 70 70 30 30th

lentelės tęsinyscontinuation of the table

Junginio Dozė Galima šių piktžolių didelė nekrozė, %Compound Dose Potential for severe necrosis of these weeds,%

Nr. No. kg/ha kg / ha Avena fatua Avena fatua Alopecarus myosuroides Alopecarus myosuroides Sorgham halepense Sorgham halepense Stellaria media Stellaria media Spomoca purpur Spomoca purple 1,0 1.0 100 100 80 80 100 100 100 100 60 60 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 15. 15th 0, 01 0, 01 20 20th 10 10th 20 20th 0 0 0 0 0,1 0.1 80 80 100 100 100 100 100 100 100 100 0, 3 0, 3 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 16. 16th 0,01 0.01 20 20th 0 0 0 0 80 80 0 0 0,1 0.1 90 90 70 70 100 100 100 100 100 100 0,3 0.3 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 17 . 17th 0,01 0.01 0 0 0 0 0 0 10 10th 0 0 0,1 0.1 10 10th 20 20th 40 40 100 100 10 10th 0, 3 0, 3 100 100 100 100 100 100 100 100 30 30th 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 18 . 18th 0,1 0.1 10 10th 10 10th 60 60 10 10th 20 20th 0,3 0.3 10 10th 70 70 70 70 10 10th 30 30th 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 19. 19th 0,01 0.01 20 20th 30 30th 100 100 100 100 0 0 0,1 0.1 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 0,3 0.3 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 20 . 20th 0, 01 0, 01 0 0 30 30th 90 90 100 100 10 10th 0,1 0.1 100 100 90 90 100 100 100 100 100 100 0, 3 0, 3 100 100 100 100 100 100 100 100 100 100 1, o 1, p 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100

lentelės tęsinys X) * continuation of table X) *

Junginio Nr. The compound No. Dozė kg/ha The dose kg / ha Galima šių piktžolių didelė nekrozė, % Possible severe necrosis of these weeds,% Avena fatua Avena fatua Alopecarus myosuroides Alopecarus myosuroides Sorgham halepense Sorgham halepense Stellaria media Stellaria media Spomoca purpur Spomoca purple 21. 21st 0,1 0.1 10 10th 50 50 100 100 100 100 90 90 0,3 0.3 30 30th 90 90 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3,0 3.0 100 100 100 100 100 100 100 100 100 100 22. 22nd 0,1 0.1 0 0 10 10th 10 10th 0 0 0 0 0,3 0.3 30 30th 40 40 90 90 10 10th 0 0 3, 0 3, 0 100 100 100 100 100 100 100 100 - - 23. 23rd 0, 01 0, 01 0 0 0 0 10 10th 10 10th 0 0 0,1 0.1 60 60 80 80 100 100 100 100 80 80 0, 3 0, 3 100 100 100 100 100 100 100 100 100 100 1,0 1.0 100 100 100 100 100 100 100 100 100 100 3, 0 3, 0 100 100 100 100 100 100 100 100 100 100 AX) A X) 0, 01 0, 01 0 0 0 0 0 0 0 0 0 0 0,1 0.1 0 0 0 0 0 0 0 0 0 0 0,3 0.3 0 0 0 0 0 0 0 0 0 0 1,0 1.0 0 0 0 0 0 0 0 0 10 10th 3, 0 3, 0 20 20th 20 20th 10 10th 10 10th 30 30th BXX1 B XX1 0,01 0.01 0 0 0 0 0 0 0 0 0 0 0,1 0.1 0 0 0 0 0 0 0 0 0 0 0,3 0.3 0 0 0 0 0 0 20 20th 10 10th 1,0 1.0 10 10th 30 30th 40 40 70 70 30 30th 3, 0 3, 0 20 20th 40 40 90 90 100 100 30 30th QXXX) Q XXX) 0, 01 0, 01 0 0 0 0 0 0 0 0 0 0 0,1 0.1 0 0 0 0 0 0 0 0 0 0 0,3 0.3 0 0 0 0 0 0 0 0 0 0 1,0 1.0 0 0 10 10th 0 0 0 0 20 20th 3, 0 3, 0 0 0 20 20th 0 0 0 0 60 60

X) -3-(2,4-dichlorfenil-1, 5, 6, 7-tetrahidro-l-metil-2Hciklopenta-(d)pirimidin-2,4(3H)-dionas,X) -3- (2,4-Dichlorophenyl-1,5,5,6,7-tetrahydro-1-methyl-2H-cyclopenta - (d) pyrimidine-2,4 (3H) -dione,

XX) -3-(4-chlor-2-fluorfenil-1,5,6,7-tetrahidro-lmetil-2H-ciklopenta-(d)pirimidin-2,4(3H)-dionas,XX) -3- (4-Chloro-2-fluorophenyl-1,5,6,7-tetrahydro-1-methyl-2H-cyclopenta- (d) pyrimidine-2,4 (3H) -dione,

XXX) -3-(2,4-difluorfenil-1,5,6,7-tetrahidro-l-metil5 2H-ciklopenta-(d)pirimidin-2,4(3H)-dionas.XXX) -3- (2,4-Difluorophenyl-1,5,6,7-tetrahydro-1-methyl-5 2H-cyclopenta- (d) pyrimidine-2,4 (3H) -dione.

Tokiu būdu, pateiktas būdas pasižymi dideliu efektyvumu, naudojant mažas junginio formas.Thus, the present invention is highly effective in the use of small compound forms.

Claims (1)

IŠRADIMO APIBRĖŽTISDEFINITION OF INVENTION Kovos su piktžolėmis būdas, apdorojant augalus arba jų augimo vietas 3-(4-chlorfenil)-2,4-diokso-l,2,3,45 tetrahidropirimidino dariniais, besiskiriantis tuo, kad, siekiant padidinti būdo efektyvumą, 3(4-chlorfenil)-2,4-diokso-l, 2, 3, 4-tetrahidropirimidino dariniais naudojami pateiktos formulės junginiai, kurioje Rx - metilas, etilas, metoksikarbonilas,A method of controlling weeds by treating plants or their growing sites with 3- (4-chlorophenyl) -2,4-dioxo-1,2,3,45 tetrahydropyrimidine derivatives, characterized in that 3 (4-chlorophenyl) ) -2,4-dioxo-1,2,3,4-tetrahydropyrimidine derivatives are compounds of the formula wherein R x is methyl, ethyl, methoxycarbonyl, R2 ~ etilas, izopropilas, n-butilas,R 2 ~ ethyl, isopropyl, n-butyl, R3 - vandenilis, fluoras,R 3 is hydrogen, fluorine, 15 R4 - metilas, etilas, n-propilas, fluormetilas, trifluormetilas, pentafluormetilas,15 R 4 - methyl, ethyl, n-propyl, fluoromethyl, trifluoromethyl, pentafluoromethyl, R5 - vandenilis, fluoras, chloras, metilas, arba R4 ir R5 kartu sudaro tri- arbaR 5 is hydrogen, fluorine, chlorine, methyl, or R 4 and R 5 together form tri or 20 tetrametileną, kurių kiekis 0,01-3 kg/ha.20 tetramethylene at rates of 0.01-3 kg / ha.
LTIP485A 1985-03-20 1993-04-13 Method of weed control LT3377B (en)

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AU627906B2 (en) 1989-07-14 1992-09-03 Nissan Chemical Industries Ltd. Uracil derivatives and herbicides containing the same as active ingredient
JP3089621B2 (en) * 1990-12-17 2000-09-18 日産化学工業株式会社 Uracil derivatives
WO1994004511A1 (en) * 1992-08-21 1994-03-03 Nissan Chemical Industries, Ltd. Pyrimidine derivative and weedkiller

Citations (2)

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Publication number Priority date Publication date Assignee Title
US3235363A (en) 1964-05-01 1966-02-15 Du Pont Method for the control of undesirable vegetation
FR2251267A1 (en) 1973-11-15 1975-06-13 Fahlberg List Veb Herbicidal compsns. - contg. 3-cyclo hexyl-5,6-trimethylene -uracil and 3-carbamoyloxy-acylanilines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235363A (en) 1964-05-01 1966-02-15 Du Pont Method for the control of undesirable vegetation
FR2251267A1 (en) 1973-11-15 1975-06-13 Fahlberg List Veb Herbicidal compsns. - contg. 3-cyclo hexyl-5,6-trimethylene -uracil and 3-carbamoyloxy-acylanilines

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ES8800173A1 (en) 1987-10-16
LTIP485A (en) 1994-10-25
ZA861892B (en) 1987-08-26
ES8708212A1 (en) 1987-10-01
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DD250452A5 (en) 1987-10-14
JPS61221178A (en) 1986-10-01

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