DK157363B

DK157363B - GAMMA AZOLYL ALCOHOLS FOR REGULATING PLANT GROWTH

Info

Publication number: DK157363B
Application number: DK375478AA
Authority: DK
Inventors: Costin Rentzea; Johann Jung; Hubert Sauter; Gerd Heilen; Bernd Zeeh
Original assignee: Basf Ag
Priority date: 1977-08-27
Filing date: 1978-08-25
Publication date: 1989-12-27
Also published as: DE2860117D1; PL107709B1; DK375478A; IL55340A0; FI782595A; SU791200A3; IL55340A; HU180206B; CS199742B2; DK157363C; BR7805534A; DD136793A5; PL209219A1

Description

1 DK 157363 B1 DK 157363 B

Opfindelsen angâr nye, værdifulde r-azolylalkoholer til régulering af plantevækst, og de er ejendommelige ved det i den kendetegnende del af krav 1 angivne.The invention relates to new, valuable r-azolyl alcohols for regulating plant growth, and are characterized by the features of the characterizing part of claim 1.

Det er kendt at anvende 2-chlorethyl-trimethylammonium-chlorid (chlorcholinchlorid, CCC) (J. Biol. Chem., 235, ® 475 (1960)) til pâvirkning af plantevæksten.It is known to use 2-chloroethyl trimethylammonium chloride (chlorocholine chloride, CCC) (J. Biol. Chem., 235, ® 475 (1960)) to influence plant growth.

Plantevækstregulatorer kan f. eks. forârsage en reduktion af længdevæksten, udl0se en spire- eller blomstrings-induktion, for0ge frostresistensen eller accelerere eller 10 hæmme dannelsen af sideskud.Plant growth regulators can, for example, cause a reduction in length growth, trigger a germination or flowering induction, increase frost resistance or accelerate or inhibit the formation of lateral shoots.

Af stor 0konomisk interesse er især forhindringen af, at korn "gâr i leje" f0r h0sten, ved hjælp af vækstregula- torer.Of particular economic interest is the prevention of grain "renting" before the fall, by means of growth regulators.

1515

Ved anvendelsen af de kendte kommercielle produkter som middel til regulering af plantevæksten, f. eks. af korn-sorter, hvorved man skal kunne opnâ en hæmmet vækst til forhindring af, at kornet gâr i leje, er virknigen ofteWhen using the known commercial products as a means of regulating plant growth, for example grain varieties, in order to be able to achieve inhibited growth to prevent the grain from renting, the effect is often

OAOA

^ ikke tilstrækkelig.^ not sufficient.

Det har vist sig, at r-azolylalkoholer, der er ejendommelige ved det i den kendetegnende del af kravet angivne, udviser en udmærket plantevækstregulerende virkning.It has been found that r-azolyl alcohols characterized by the characterizing part of the claim exhibit an excellent plant growth regulating effect.

25 r-azolylalkoholerne if01ge opfindelsen egner sig ved talrige planter udmærket til regulering af væksten, hvilket især ytrer sig ved en reduktion af længdevæksten.The 25-azolyl alcohols of the invention are suitable for numerous plants excellent for regulating growth, which is particularly evident by a reduction in length growth.

Virkningen er bedre end ved kendte vækstregulatorer.The effect is better than with known growth regulators.

3030

Virkningen viser sig frem for ait ved korn, f. eks. hvede, rug, byg, ris og havre, men ogsâ ved dikotyle planter (f. eks. solsikker, tomater, vinranker, bomuld, raps) og forskellige prydplanter, sâsom poinsettier og 35 hibiskus. De behandlede planter udviser i overensstem-The effect is evident in cereals, such as wheat, rye, barley, rice and oats, but also in dicotyledonous plants (eg sunflowers, tomatoes, vines, cotton, rapeseed) and various ornamental plants, such as poinsettias and 35 hibiscus. The treated plants exhibit in accordance with

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2 melse dermed en lavere vækst; desuden kan man iagttage en m0rkere bladfarvning.2 thus a lower growth; moreover, a darker leaf staining can be observed.

r-azolylalkoholeme if0lge opfindelsen kan bâde tilf0res 5 til kulturplanterne via jorden, dvs. gennem r0dderne, og ved spr0j tning via bladet. Pâ grund af den h0je plante-forligelighed kan den anvendte mængde varieres stærkt; sædvanligvis antages det dog, at tilf0rte mængder mellem 0,25 og 12 kg/ha er tilstrækkelige.The r-azolyl alcohols of the invention can both be added to the culture plants via the soil, i.e. through the roots, and by spraying through the leaf. Because of the high plant compatibility, the amount used can be greatly varied; however, it is usually assumed that added amounts of between 0.25 and 12 kg / ha are sufficient.

10 R1 betyder f. eks. methyl, isopropyl, n-butyl, sek.-bu-tyl, isobutyl, tert.-butyl, furanyl, thiophenyl, naph-thyl, diphenylyl, phenyl, p-tolyl, m- og p-methoxyphenyl, p-fluorphenyl, p-chlorphenyl eller 2,4-dichlor-phenyl.R 1 means, for example, methyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, furanyl, thiophenyl, naphthyl, diphenylyl, phenyl, p-tolyl, m methoxyphenyl, p-fluorophenyl, p-chlorophenyl or 2,4-dichlorophenyl.

15 R2 betyder f. eks. tert.-butyl, furanyl, 2-methylfuranyl, thiophenyl, pyridyl, naphthyl, phenyl, p-tolyl, p-isopropylphenyl, o- og p-methoxyphenyl, 2,3-dimethoxyphenyl, o-hydroxyphenyl, p-chlorphenyl, m- og p-20 bromphenyl, 2,4-dichlorphenyl, 2,4-dibromphenyl eller p-nitro-phenyl.R 2 means, for example, tert-butyl, furanyl, 2-methylfuranyl, thiophenyl, pyridyl, naphthyl, phenyl, p-tolyl, p-isopropylphenyl, o- and p-methoxyphenyl, 2,3-dimethoxyphenyl, o-hydroxyphenyl , p-chlorophenyl, m- and p-bromophenyl, 2,4-dichlorophenyl, 2,4-dibromophenyl or p-nitrophenyl.

Forbindelserne if01ge opfindelsen med formlen I er nye og kan fremstilles pâ f01gende mâde. De fremkommer f. eks., 25 nâr man reducerer b-azolylketoner med formlen 0The compounds of the invention of formula I are novel and can be prepared in the following manner. They appear, for example, when reducing b-azolyl ketones of formula 0

KK

R1-C-CH0-CH-R2 IIR1-C-CHO-CH-R2 II

2 I Az 30 hvori R1, R2 og Az har den f0r angivne betydning. Reduk-tionen kan f. eks. gennemf0res: a) med komplexe hydrider, sàsom natriumborhydrid i nær-35 værelse af et polært opl0sningsmiddel, som f. eks. metha-nol, eller med lithiumalanat i tetrahydrofuran, ved temperaturer mellem 0 °C og 30 °C og pàf01gende hydro-2 In Az 30 wherein R1, R2 and Az have the meaning given above. The reduction can be carried out, for example: a) with complex hydrides such as sodium borohydride in the presence of a polar solvent, such as methanol, or with lithium alanate in tetrahydrofuran, at temperatures between 0 ° C and 30 ° C and subsequent hydro

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3 lyse, f. eks. med vandige baser eller syrer, eller b) med hydrogen i nærværelse af en katalysator, sâsom platin eller Raney-nikkel og i nærværelse af et polært 5 opl0sningsmiddel, sâsom methanol, éthanol, isopropanol, ved en temperatur mellem 40 °C og 60 °C og et tryk mellem 1 og 100 bar, eller c) med aluminiumisopropylat i nærværelse af et inert 10 opl0sningsmiddel ved en temperatur mellem 40 og 120 ’C og efterf0lgende hydrolyse, f. eks. med vandig saltsyre.3 lysis, e.g., with aqueous bases or acids, or b) with hydrogen in the presence of a catalyst, such as platinum or Raney nickel, and in the presence of a polar solvent, such as methanol, ethanol, isopropanol, at a temperature between Or 40 ° C and a pressure between 1 and 100 bar, or c) with aluminum isopropylate in the presence of an inert solvent at a temperature between 40 and 120 ° C and subsequent hydrolysis, e.g., with aqueous hydrochloric acid.

De sâledes fremkomne forbindelser med formlen I bliver i henhold til de sædvanlige metoder isoleret og eventuelt 15 renset.The compounds of formula I thus obtained are isolated and purified, according to the usual methods.

Udgangsstofferne med formlen II kan fremstilles pâ f01gende mâde.The starting materials of formula II can be prepared in the following manner.

20 Man fremstiller 0-(l,2,4-triazol-(l)-yl- og Æ-imidazolyl-ketonerne med formlen II, nâr man omsætter tilsvarende substituerede a,0-umættede ketoner med de 0nskede azoler i nærværelse af opl0snxngs- eller fortyndingsmidler ved temperaturer mellem 20 og 80 °C, eller nâr man i stedet 25 for a,0-umættede ketoner omsætter de tilsvarende alde- hyder og ketoner i nærværelse af azoler og eventuelt i nærværelse af et fortyndingsmiddel.The O- (1,2,4-triazol- (1) -yl- and? -Imidazolyl ketones of formula II) are prepared when reacting similarly substituted α, O-unsaturated ketones with the desired azoles in the presence of solution. or diluents at temperatures between 20 and 80 ° C or when substituting 25, for example, unsaturated ketones, the corresponding aldehydes and ketones are reacted in the presence of azoles and optionally in the presence of a diluent.

30 3530 35

DK 157363 BDK 157363 B

44

Forskrift ARegulation A

ch3CH3

CH^-CO-CHo-CHCH ^ -CO-CHO CH

a chJ/ 2and chJ / 2

En opl0sning af 11 g (0,11 mol) 3,3-dimethylbutan-2-on og 14 g (0,1 mol) p-chlorbenzaldehyd i 120 ml éthanol blandes med 10 ml 20% vandig natronlud og holdes i om-10 r0ring 2 timer ved 50 °C. Efter tilsætning af 13,8 g (0,2 mol) 1,2,4-triazol efterr0res blandingen i yderligere 8 timer ved 50 °C. Derpâ bliver opl0sningsmidlet afdestilleret, og den tilbageblivende remanens fordeles mellem 300 ml vand og 300 ml ether.A solution of 11 g (0.11 mol) of 3,3-dimethylbutan-2-one and 14 g (0.1 mol) of p-chlorobenzaldehyde in 120 ml of ethanol is mixed with 10 ml of 20% aqueous sodium hydroxide solution and kept for about 10 minutes. stir for 2 hours at 50 ° C. After adding 13.8 g (0.2 mole) of 1,2,4-triazole, the mixture is stirred for an additional 8 hours at 50 ° C. The solvent is then distilled off and the residue is partitioned between 300 ml of water and 300 ml of ether.

1515

Den etheriske opl0sning t0rres over CaSO^, filtreres og gasses med t0r hydrogenchlorid ved 5 til 10 °C.The ethereal solution is dried over CaSO4, filtered and gassed with dry hydrogen chloride at 5 to 10 ° C.

Man opnâr 24,3 g (74% af den teoretiske værdi) hydro-20 chlorid af l-[l,2,4-triazolyl-(l)-]-l-(4'-chlorphenyl)- 4,4-dimethylpentan-3-on som hvide krystaller med smel-tepunkt 139-141 °C.24.3 g (74% of theory) of hydrochloride of 1- [1,2,4-triazolyl- (1) -] - 1- (4'-chlorophenyl) -4,4-dimethylpentane are obtained. -3-one as white crystals with melting point 139-141 ° C.

F01gende ketoner kan f. eks. anvendes som udgangs-25 materialer.The following ketones may be used, for example, as starting materials.

30 3530 35

Tabel 1Table 1

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5 R^CO-CHp-CH-R2 'R 2 CO-CH 2 -CH 2 R 2

* I* I

5 Λ ί P Smp. Smp. (hydro-5 ί ί P Mp. Mp. (hydro-

Nr. R R X Y Z °C chloridj DCNo. R R X Y Z ° C chloride j DC

iQ 1 (CH3)3C- ci-^Oy ’ N N; CH 139-141iQ 1 (CH3) 3C- C1-6 O 'N N; CH 139-141

‘2 CH3- (CH3)3C- ‘ N N CH'2 CH3- (CH3) 3C-' N N CH

3 (CH3)2CH- ô- N' N ' CH ; 53-55 15 .—i 4 (CH3)2CH- C1-/qV N N CH 118-120 5 sek.-C^H^- O- N N CH 41-43 20 6 iso-C4H9- O- N N CH 163-166 7 (CH3)3C- O- N N CH 69-71 8 ^CH3^3c“ CH, N N CH 49-513 (CH3) 2CH- ô- N 'N' CH; 53-55 15.-i 4 (CH3) 2CH- C1- / qV NN CH 118-120 5 sec.-C ^ H ^ - O- NN CH 41-43 20 6 iso-C4H9-O-NN CH 163- 166 7 (CH3) 3C- O- NN CH 69-71 8 ^ CH3 ^ 3c “CH, NN CH 49-51

25 Y25 Y

9 (CH3)3C- N N CH 118-120 10 sek.-C/,Ηο- γΞ/” N. N CH. harpiks 30 4 9 11 iso-C. Hq ' \2r N N CH 167-169 © 35 12 (CH,),C- N N CH 162-164 © 13 (CH,),C- nQP~ N CH CH · 68-699 (CH3) 3C- N N CH 118-120 10 sec.-C /, Ηο- γΞ / ”N. N CH. resin 30 4 9 11 iso-C. Hq '\ 2r N N CH 167-169 © 35 12 (CH,), C- N N CH 162-164 © 13 (CH,), C- nQP ~ N CH CH · 68-69

OISLAND

Tabel 1 (fortsat)Table 1 (continued)

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66

Nr. R1 R2 X Y Z cSoridT5?” 5 14 (CH3)3Ct CH N N .130-132 15 (GH3)3C- CH N CH 89^91 10 16 (CH3)3C- Cl-^ N .CH CH 65-67 17 (CH3)3C- Br^ . N N CH 142-145 15 18 (CH3)3C- Cl w N N CH 154-156No. R1 R2 X Y Z cSoridT5? " 5 14 (CH3) 3Ct CH N N .130-132 15 (GH3) 3C- CH N CH 89 ^ 91 10 16 (CH3) 3C- Cl- ^ N .CH CH 65-67 17 (CH3) 3C- Br ^. N N CH 142-145 15 18 (CH3) 3C- Cl w N N CH 154-156

Cl 2o 19 (ch3)3c- Cl CH N CH 73-77Cl 2o 19 (ch3) 3c- Cl CH N CH 73-77

Cl 20 (CH3)3C- 0Η3-^^ N N CH 153-155 25 21 (CH3)3C- CH3-^- CH N CH 98-100 22 (CH3)3C- /QV N N CH 141-143Cl 20 (CH3) 3C-O3 - ^^ N N CH 153-155 25 21 (CH3) 3C- CH3 - ^ - CH N CH 98-100 22 (CH3) 3C- / QV N N CH 141-143

30 CH30 CH

23 (ch3)3c- . n n ch 155-157 ch3 '—' 35 24 (CH3)3C-· CH^ N N CH 158-161 25 (CH3)3C- Br N N CH 104-10623 (ch3) 3c-. n n ch 155-157 ch3 '-' 35 24 (CH3) 3C- · CH ^ N N CH 158-161 25 (CH3) 3C- Br N N CH 104-106

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77

Tabel 1 (fortsat)Table 1 (continued)

Mr· r1 r2 * Y z §T ; C^rid^g' 5 26 (CH3)3C- N K CH 164-167 27 f~\ ^JV N N CH 106 ' ' CCH, 10 28 N N CH 142-144 29 /—v CH3CL.OCH3 N N CH 101-102 Q- 30 (oV (ÔV N N CH 95-97 '— \-^/pCH3 20 31 CH3°^> (Qs N N CH 134-135 32 Cl CH3 <& N N CH 81-82 • 33 CH3°70V N N CH 126-128 .Mr · r1 r2 * Y z §T; C ^ rid ^ ^ g g 26 (CH3) 3C- NK CH 164-167 27 f f ~ \V NN CH 106 'CCH, 10 28 NN CH 142-144 29 / -v CH CHCL.OCH3 NN CH 101-102 Q- 30 (oV (ÔV NN CH 95-97 '- \ - ^ / pCH3 20 31 CH3 ° ^> (Qs NN CH 134-135 32 Cl CH3 <& NN CH 81-82 • 33 CH3 ° 70V NN CH 126 -128.

25 '—' 34 (0)- N N CH 126 CH3°>_ /-* ' 30 35 <0> O-, N· N CH 130-133 36 CH30^y N N CH 112-114 37 (CH3)^C- N N CH 76-79 (CH3)3C- N N GH 104-10625 '-' 34 (0) - NN CH 126 CH3 °> _ / - * '30 35 <0> O-, N · N CH 130-133 36 CH30 ^ y NN CH 112-114 37 (CH3) ^ C - NN CH 76-79 (CH3) 3C- NN GH 104-106

Tabel 1 (fortsat)Table 1 (continued)

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88

Nr. R?" X Y Z Smp* Smp. (hvdro- _0 C chloridj °ç 5 39 <cbhC- » » CH 125-127 (oV- (CH,),C- N N CH 136-138 40 Y_/ 33 (o) 10 « : C%-<Ô)- (C^C- * » “ 128-13° « ‘Cli3>3C- " M CH 10°-102 43' 01-/ÔY <C%>3C' " " CH 113:1-15 44 ! Cl-Z^Y (CH3>3C- “ k ch ^-12^ 45 CI^V <CH3>3C- * " CH 7°-72No. R? XYZ Mp * Mp (Hydro- _0 C chloridej ° ç 5 39 <cbhC- »» CH 125-127 (oV- (CH,), C- NN CH 136-138 40 Y_ / 33 (o) 10 :: C% - <Ô) - (C ^C- * »“ 128-13 ° '' Cli3> 3C- "M CH 10 ° -102 43" 01- / ÔY <C%> 3C ' : 1-15 44! Cl-Z ^ Y (CH3> 3C- "k ch ^ -12 ^ 45 CI ^ V <CH3> 3C- *" CH 7 ° -72

ClCl

Br N_ (CH„kC- N N CH 114-116 46 {oy 20 47 (0)-(0)- (CH3)3C- * iJ CH 127-128 48 (CH3)3C- (CH3>3C- 11 !1 CH 98-99 , , , \Or- N N CH 106-108 25 se r\ ®- * "CH 146-148Br N_ (CH2 kC- NN CH 114-116 46 {oy 47 (0) - (0) - (CH3) 3C- * CH CH 127-128 48 (CH3) 3C- (CH3> 3C-11! 1 CH 98-99,,, \ Or- NN CH 106-108 25 see r \ ®- * "CH 146-148

Br och3 5i (ch3)3c- ' (θ>- " * CH 92'95 _^°CH3 30 - <5> O-Br and 35i (ch3) 3c- (θ> - "* CH 92'95 _ ^ ° CH3 - <5> O-

«! <o>- .Qr HSCH'! <o> - .Qr HSCH

54 ClToV f\ N N CH 78-81 35 Wn 55 H5C0-(g)- N N CH 108-11054 ClToV f \ N N CH 78-81 35 Wn 55 H5C0- (g) - N N CH 108-110

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99

Det f01gende eksempel angâr fremstilling af r-azolylalko-holerne if01ge opfindelsen.The following example relates to the preparation of the r-azolyl alcohols according to the invention.

Eksempel 1 5Example 1 5

y—Ny-N

P X,> ch,-c-ch-ch9-ch 10 CEÎ \§)-C1 la) I en opl0sning af 29,1 g l-[l,2,4-triazolyl-(l)]-l-15 (4'-chlorphenyl)-4,4-dimethylpentan-3-on i 300 ml metha-nol indf0res under omr0ring og isk0ling ved 3 til 8 °C portionsvis 5,9 g natriumborhydrid. Efter 8 timers omr0ring ved stuetemperatur inddampes blandingen. Rema-nensen holdes under omr0ring i 1 time med 150 ml 4% na-20 tronlud og ekstraheres med 250 ml methylenchlorid. Det organiske lag t0rres over NaSO^ og koncentreres i vakuum.PX,> ch, -c-ch-ch9-ch 10 CEÎ \ §) -C1a) In a solution of 29.1 g of 1- [1,2,4-triazolyl- (l)] - 15 ( 4'-Chlorophenyl) -4,4-dimethylpentan-3-one in 300 ml of methanol is introduced with stirring and ice-cooling at 3 to 8 ° C, 5.9 g of sodium borohydride in portions. After stirring for 8 hours at room temperature, the mixture is evaporated. The residue is stirred for 1 hour with 150 ml of 4% sodium hydroxide solution and extracted with 250 ml of methylene chloride. The organic layer is dried over NaSO4 and concentrated in vacuo.

Den tilbageblivende faste, farvel0se remanens vaskes med 40 ml petroleumsether og frasuges.The remaining solid, colorless residue is washed with 40 ml of petroleum ether and suctioned off.

25 Man opnâr 26,1 g (89% af den teoretiske værdi) 1-[1,2,4-triazolyl-(1)]-1-(4'-chlorphenyl)-4,4-dimethylpentan-3-ol med smeltepunkt 104-106 °C.26.1 g (89% of theoretical value) of 1- [1,2,4-triazolyl- (1)] - 1- (4'-chlorophenyl) -4,4-dimethylpentan-3-ol with mp 104-106 ° C.

29,1 g l-[l,2,4-triazolyl-(l)]~l-(4'-chlorphenyl)-4,4-30 dimethylpentan-3-on opl0ses i 100 ml vandfri ether. Denne opl0sning bliver langsomt dryppet til en suspension af 5,7 g lithiumalanat i 200 ml vandfri ether. Blandingen opvarmes i 3 timer under tilbagesvaling og blandes derpè under isafk0ling drâbevis med 150 ml isvand. Derpà r0res 35 blandingen endnu med 200 ml 20% (vægt-%) vandig natronlud og ekstraheres tre gange, hver gang med 150 ml ether. Den organiske fase t0rres over NaSO^ og koncentreres i29.1 g of 1- [1,2,4-triazolyl- (1)] -1- (4'-chlorophenyl) -4,4-30 dimethylpentan-3-one are dissolved in 100 ml of anhydrous ether. This solution is slowly dropped to a suspension of 5.7 g of lithium alanate in 200 ml of anhydrous ether. The mixture is heated at reflux for 3 hours and then mixed dropwise with ice-cooling dropwise with 150 ml of ice water. The mixture is then stirred with 200 ml of 20% (wt%) aqueous baking soda and extracted three times, each time with 150 ml of ether. The organic phase is dried over NaSO4 and concentrated

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10 vakuum. Det delvist krystalliserede bundfald sammenr0res med petroleumsether og vaskes.10 vacuum. The partially crystallized precipitate is stirred with petroleum ether and washed.

Man opnâr 24,9 g (85% af den teoretiske værdi) 1-[1,2,4-5 triazolyl-(l)]-l-(4,-chlorphenyl)-4,4-dimethylpentan-3-ol med smeltepunkt 104-106 °C.24.9 g (85% of theory) of 1- [1,2,4-5 triazolyl- (1)] - 1- (4, -chlorophenyl) -4,4-dimethylpentan-3-ol are obtained. mp 104-106 ° C.

Pâ tilsvarende mâde kan man fremstille de i den f01gende tabel 2 angivne forbindelser.Similarly, the compounds listed in the following Table 2 can be prepared.

1010

Tabel 2Table 2

?H? H

R^CH-C^-CH-R2 15 ÀzR ^ CH-C ^ -CH-R2 15 15z

Nr. R1 R2 Az Smp. IR-bând °C cm”·1 λ 2 CH^ (CH^C- harPiks < A-V /N. 745, 1015, 1140, 3 (CH, pCH- // \ J) ^ar- 1280, 1505 , 2970.No. R1 R2 Az Mp. IR band ° C cm ”· 1 λ 2 CH CH (CH₂C-resPiks <A-V / N. 745, 1015, 1140, 3 (CH, pCH-// \ J)) -1280, 1505, 2970.

3 \0/ V7' piks 3110, 3450 (film) /7Z\ / 675, 1010, 1088, 4 (CH·,) o CH- Cl-< (yy k' \ har- 1270, 1490, 2875, 25 ^ 2 \_N/ piks 295°» 3300 aL 680, 745, 1015, har- 1135, 1280, 1503, PÎkS ^90 " 3280 ^mm qo <<,. η π yfl üar- 748. 1007, 1135, 30 6 îso-C^Hg // N > piks 1274, 1505 , 2920.3 \ 0 / V7 'pixel 3110, 3450 (film) / 7Z \ / 675, 1010, 1088, 4 (CH ·,) o CH- Cl- <(yy k' \ har-1270, 1490, 2875, 25 ^ 2 \ _N / pix 295 ° »3300 aL 680, 745, 1015, har- 1135, 1280, 1503, PÎkS ^ 90" 3280 ^ mm qo <<,. Η π yfl üar- 748. 1007, 1135, 30 6 îso -C ^ Hg // N> pix 1274, 1505, 2920.

n7 2960, 3280 (film) 35n7 2960, 3280 (film) 35

Tabel 2 (fortsat) 11Table 2 (continued) 11

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nr. R1 R2 Az Smp. IR-bând _° C cm"1_ i 7 (CH,),C- fj 1 \ har- 685, 750, 1075, D D '\n>- V m/ Piks 1280, !506, 2890.No. R1 R2 Az Mp. IR band _ ° C cm-1 in 7 (CH,), C-fj 1 \ har- 685, 750, 1075, D D '\ n> - V m / Pix 1280, 506, 2890.

u ,iNI 2970, 3380 (film) , . ΙΓ\ N > har- 780, 1005, 1133, 8 (CH,),C- CH,< > Piks 1270, 2950, 3110, ^ 2 N 3375 (film) 9 (CH ) C- il if N^\ har" 766» 1005* 1075, 9 ^h3;3c u u N \ piks 1275> 1365> 1500u, iNI 2970, 3380 (film) ,. ΙΓ \ N> har- 780, 1005, 1133, 8 (CH,), C- CH, <> Pixels 1270, 2950, 3110, ^ 2 N 3375 (film) 9 (CH) C-il if N "766» 1005 * 1075, 9 ^ h3; 3c u N \ pix 1275> 1365> 1500

Xs^ \»n7 2982, 3350 (film) (ÔV /Nv 10 sek.-C/HQ V-/ N \ 97-99 (ô) / \_/ '—N' N > 94-96 (threo-) N^n/ 105-107 (erytfcro-) N X 100-105 N—n/ ,—, 660, 915, 1012, i -2 ('rjH ) C- ci a (~)\ N y hap- 1075, 1010, 1490, 13 (CH3J3C l1\^/ V/ piks 2955 , 3400 (KBr)Xs ^ \ »n7 2982, 3350 (film) (ÔV / Nv 10 sec.-C / HQ V- / N \ 97-99 (ô) / \ _ / '—N' N> 94-96 (threo-) N ^ n / 105-107 (erythfcro-) NX 100-105 N-n /, -, 660, 915, 1012, i -2 ('rjH) C-ci a (~) \ N y hap-1075, 1010 , 1490, 13 (CH3J3C1 / 1 / V / pix 2955, 3400 (KBr)

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Tabel 2 (fortsat) 12 i\ir. R·*· R^ Az Smp. IR-bând 0 C cm"-1· « (CH3)3C- Br^- 120-122 15 (CH3)3C- Cl/ Q Y N J 118-120Table 2 (continued) 12 i \ ir. R · R · Az m.p. IR band 0 C cm -1 -1 (CH3) 3C-Br2 - 120-122 (CH3) 3C-Cl / Q Y N J 118-120

10 V—( \-W10 V— (\ -W

ClCl

'N'N

/ \ /~~\ ^ Tr 662, 735, 820, 16 (CH^UC- Cl/nV P ! har- 1075,1470,1585, 0 \ / -N piks 2960, 3360 (KBr)Tr 662, 735, 820, 16 (CH ^ UC- Cl / nV P! Har- 1075,1470,1585, 0 \ -N p 2960, 3360 (KBr)

Cl Λ 15 , N /“\ ^ \ 680, 790, 1080, 17 (CKUUC- OHτ{Γ)\ N }y har- 1135, 1510, 2885, -7 D y \ZL/ \_W piks 2960, 3400 (KBr) !B (CH3)3C- CHV? 98-99 ολ , . / \ 665, 700, 1010, 20 19 (0¾) c- < Ο V N N har- 1140, 1205, 1505, \ / \.r/ piks 2885, 2960, 3370 (film) CH^ __ jIj· 20 (CH3)3C- ΚΓ ^ 102-104Cl Λ 15, N / \ \ 680, 790, 1080, 17 (CKUUC- OHτ {Γ) \ N} y har- 1135, 1510, 2885, -7 D y \ ZL / \ _W pix 2960, 3400 ( KBr)! B (CH3) 3C- CHV? 98-99 ολ ,. / \ 665, 700, 1010, 20 19 (0¾) c- <Ο VNN har- 1140, 1205, 1505, \ / \ .r / pix 2885, 2960, 3370 (film) CH ^ __ jIj · 20 (CH3) 3C- ΚΓ ^ 102-104

CH-p v—HCH-p v-H

25 5 , , x /—v 660, 680, 1030, 21 (CH~),C- CH^Oi ny N \ har- 1250,1512,1610.5, x / -v 660, 680, 1030, 21 (CH CH), C-CH₂O in new N, has 1250, 1512, 1610.

'—' piks 2950, 3360 (film) 22 (CH3)3C- Br-/oy N (J 154-156 30 ^ \_/ V-N7 750, 886, 1073, 23 (CH,)3C- OpN-/ QV N Y har- 1137, 1352, 1525, \—/ V,/ piks 2980, 3035, 3250, (film) 35"-" pix 2950, 3360 (film) 22 (CH3) 3C- Br- / oy N (J 154-156 30 ^ \ _ / V-N7 750, 886, 1073, 23 (CH,) 3C- OpN- / QV NY has- 1137, 1352, 1525, \ - / V, / pix 2980, 3035, 3250, (movie) 35

, DK 157363 B, DK 157363 B

} ' ’ 13} '' 13

Tabel 2 (fortsat)Table 2 (continued)

Nr. R1 R2 Az Smp. IR-bând _°C. cm~ _ 7 Δ (- -^0CH3 5 24 ( U. / \ \ har- 750, 1008, 1131, S/ <2> Ό S.No. R1 R2 Az Mp. IR band _ ° C. cm ~ _ 7 Δ {- - ^ 0CH3 5 24 {U. / \ \ har- 750, 1008, 1131, S / <2> Ό S.

V v 9r ^—λ /—/511 740, 1000, 1125, 25 // \\ /r\ ^ har- 1270, 1450, 1497, \^y if piks 1595, 2910, 3230,V v 9r ^ —λ / - / 511 740, 1000, 1125, 25 // \\ / r \ ^ har- 1270, 1450, 1497, \ ^ y if pix 1595, 2910, 3230,

CH*0 jOCH, NCH * 0 YOCH, N

O3 "> 3 / \ 748, 1005, 1060, AT\ \ /> ha1r" 1272 » 1479, 1585, \ Ο Γ k-N7 Plks 2930 , 3290 (film) \_/ PCH3 f / \ /—( / \ 753, 830, 1028, 27 ( O V /yv \ > har- 1245, 1491, 1509, \ / W Γ \\_N/ Plks 1601, 1609, 2830, N-f 2930 , 2950 , 3350, 0CH-* (film) _/ 2 jj 15 28 CH3°/ÔV (oV f" \ har- 1240,^1487^1596.O3 "> 3 / \ 748, 1005, 1060, AT \ \ /> ha1r" 1272 »1479, 1585, \ Ο Γ k-N7 Plks 2930, 3290 (film) \ _ / PCH3 f / \ / - (/ \ 753, 830, 1028, 27 (OV / yv \> har- 1245, 1491, 1509, \ / W Γ \\ _ N / Plks 1601, 1609, 2830, Nf 2930, 2950, 3350, 0CH- * (film) _ / 2 jj 15 28 CH3 ° / ÔV (oV f "\ har- 1240, ^ 1487 ^ 1596.

N—' '—' \ </ Piks 2925, 3330 (film) '—N'N— "" - "\ </ Pixels 2925, 3330 (movie)" —N "

NN

29 d^o) ce3{q)· \_y 137"139 20 743, 1009, 1032, •γη // H CH-O·/ r>V N \ har- 1140, 1180, 1252, 30 403- 3 V // piks 151l! 1607 ; 2833; v-w/ 2930, 3112, 3270 jjf (film) M Ο Ό ^ IIS"- 25 t CH3°\ /-k 740, 1006, 1035, 37 )-V // \\ N > har- 1133, 1260, 1480, (nV SrJ* 7 Piks 1595 , 2928 , 3320, \u^ ' N (film) t /—\ _ 742 , 828, 1009, 30 33 CHOVoV /TJ N \ har- 1030,1242,1501, 5 W piks 1697,^2925, 3320, t ,, , /=^. /N\ 665, 748, 1005, 34 (CH.UC- 4 Λ N > har- 1072, 1132, 1370, VJ Piks 1428, 1470, 1585, “ 2950, 3350 (film) 3529 d ^ o) ce3 {q) · \ _y 137 "139 20 743, 1009, 1032, • γη // H CH-O · / r> VN \ har- 1140, 1180, 1252, 30 403-3 V / / pixel 151l! 1607; 2833; vw / 2930, 3112, 3270 jf (film) M Ο Ό ^ IIS "- 25 t CH3 ° \ / -k 740, 1006, 1035, 37) -V // \\ N> har- 1133, 1260, 1480, (nV SrJ * 7 Peaks 1595, 2928, 3320, \ n ^ A (film) t / - \ _ 742, 828, 1009, 30 33 CHOVoV / TJ N \ har-1030, 1242.1501, 5W pixel 1697, ^ 2925, 3320, t ,,, / = ^ ./N \ 665, 748, 1005, 34 (CH.UC- 4 Λ N> har- 1072, 1132, 1370, VJ Pixels 1428, 1470, 1585, "2950, 3350 (movie) 35

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Tabel 2 (fortsat) 14 nr. R1 R2 Az Smp. IR-bând ° C. cm"-1· 5 }i Q (CH3)3C- ^ 113-115Table 2 (continued) 14 No. R1 R2 Az Mp. IR band ° C. cm -1 -1 5} in Q (CH 3) 3 C- 113-115

,_, A, _, A

36 (3 (CH3>3C' Y/ 1W_15° (ûV , .36 (3 (CH3> 3C) Y / 1W_15 ° (uv ,.

10 37 V-( (CH3) C- N \ 178-180 \o/ /—\ , „ 820,1140, 1275, 38 CH3\ O / (CH3)3C- N > har- 1505. 2960, 3020, ^ W ^ 5 Piks (film) t _ / \ , . 680, 840, 1135, 15 39 F\Or (CHjJÆ N > har- 1220, 1510, I6Ô5.37 V- ((CH3) C- N \ 178-180 \ o / / - \, 820, 1140, 1275, 38 CH3 \ O / (CH3) 3C- N> har- 1505. 2960, 3020, ^ W ^ 5 Pixels (film) t _ / \,. 680, 840, 1135, 15 39 F \ Or (CHjJÆ N> har- 1220, 1510, I6Ô5.

13 .Vl/ 5 5 „/ piks 2960, 3350 (film) t N.13.Vl / 5 5 "/ pix 2960, 3350 (movie) to N.

40 Cl/oV (CH,),C- N- )> harp- 834, 1012, 1090, \ / 5 ^ piks 1140, 1490, 1510, , 2975, 3110, 3300 (film) 20 * / V 740, 835, 1015, 41 Cl-( O > (CB,),C- har- 109o, 1230, 1490.40 C1 / oV (CH2), C- N-> Harp- 834, 1012, 1090, \ / 5 pixel 1140, 1490, 1510,, 2975, 3110, 3300 (film) 20 * / V 740, 835 , 1015, 41 Cl- (O> (CB,), C- har- 109o, 1230, 1490.

\_/ 2 5 _N piks 2970 , 3350; (film) 42 <πφ (CH3)3C- ‘ 130-132 25 \\ _ / 2 5 _N pix 2970, 3350; (film) 42 <πφ (CH3) 3C- '130-132 25 \

Cl * B\_ 700, 750, 1068, 43 /-\ (CH,),C- N > . har- 1140, 1201, 1276, (o> 33 1^’(MS 2965' t ,n ,, Γ\ Γ~\ , v 699, 769,843, 30 44 OK OY (CH,),C- N /) har- 1009, 1139, 1273, V_y 3 3 piks 1370, 1486, 1502.Cl * B \ _ 700, 750, 1068, 43 / - \ (CH,), C- N>. har- 1140, 1201, 1276, (o> 33 1 ^ '(MS 2965' t, n ,, Γ \ Γ ~ \, v 699, 769,843, 44 44 OK OY (CH,), C-N /) has - 1009, 1139, 1273, V_y 3 3 pixels 1370, 1486, 1502.

“ 2965, 3320 (film) f 45 (ch3)3c- (ch3)3c- 120 35“2965, 3320 (film) f 45 (ch3) 3c- (ch3) 3c- 120 35

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Tabel 2 (fortsat) 15Table 2 (continued) 15

Nr. R1 R2 Az Smp. IR-bând _______C cm~_ 46 lî~\\ (o\- £96, 735, 1002, <w** Vl/ \ // ter- H31, 1271, 1496.No. R1 R2 Az Mp. IR band _______C cm ~ _ 46 l ~ ~ \\ (o \ - £ 96, 735, 1002, <w ** Vl / \ // ter- H31, 1271, 1496.

0 Piks 2912, 3260 (film] ^ocîî3 α\0>- ΜχΝν> 735, 804,882, \_/ N\\ / 1005, 1019, 1245, -LU - · BrS ^-N Plks 1^2, 2930, 330 y0CS3 - (fllB) 4B {CRr,hc- ΛΛ. har- 111,¾¾.¾¾.0 Pixels 2912, 3260 (film) ^ ocîî3 α \ 0> - ΜχΝν> 735, 804,882, \ _ / N \\ / 1005, 1019, 1245, -LU - · BrS ^ -N Plks 1 ^ 2, 2930, 330 y0CS3 - (fllB) 4B {CRr, hc- har. har- 111, ¾¾.¾¾.

Vl/ Plks 2950, 3360 (film^ 15 49 ,^£/~ Νν.^ harpiks . 50 (Ô)- O" \/ /^X 832, 1012, 1080, 20 ςι Cl/O Y V Γ N jj har- 1137, 1276, 1433, 51 Vi/ '—»N Vrf Piks 1489, 1592 , 3300 (film) f r-\ /V /V 829, 1026. 1167, 52 H^Co/oY \\ Γ N /> har- 1241, 1504, 1590, 3 \L_n' piks 3300 (film) 25 30 35Vl / Plks 2950, 3360 (film ^ 15 49, ^ £ / ~ Νν. ^ Resin. 50 (Ô) - O "\ / / ^ X 832, 1012, 1080, 20ς Cl / OYV Γ N jj har-1137 , 1276, 1433, 51 Vi / '- »N Vrf Piks 1489, 1592, 3300 (film) f r- \ / V / V 829, 1026. 1167, 52 H ^ Co / oY \\ Γ N /> have- 1241, 1504, 1590, 3 \ L_n 'pix 3300 (movie) 25 30 35

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1616

Anvendelsen af de aktive stoffer if0lge opfindelsen foregàr f. eks. i form af direkte udspr0jtelige opl0s-ninger, pulvere, suspensioner, ogsâ h0jprocentige van-dige, olieagtige eller lignende suspensioner eller dis-5 persioner, emulsioner, oliedispersioner, pastaer, pud-ringsmidler, udstr0mningsmidler, granulater ved udspr0jt-ning, tâgedannelse, forst0vning eller udhældning. Anvendelsesformerne retter sig helt efter anvendelses-formàlene; de skal i hvert tilfælde sikre den finest 10 mulige fordeling af de aktive stoffer if01ge opfindelsen.The use of the active substances according to the invention is carried out, for example, in the form of directly injectable solutions, powders, suspensions, as well as high percent aqueous, oily or similar suspensions or dispersions, emulsions, oil dispersions, pastes, powders. , emulsifiers, granules by spraying, forming, spraying or pouring. The forms of use are entirely according to the uses; in each case they must ensure the finest possible distribution of the active substances according to the invention.

Med henblik pà fremstilling af direkte udspr0jtelige opl0sninger, emulsioner, pastaer og oliedespersioner kommer mineraifraktioner med middelh0jt til h0jt koge-15 punkt, sâsom Petroleum eller dieselolie, desuden kul- tjæreolier osv., samt olier af vegetabilsk eller animalsk oprindelse, alifatiske, cycliske og aromatiske carbonhydrider, f. eks. toluen, xylen, paraffin, tetra-hydronaphthalen, alkylerede naphthalener eller disses 20 dérivater, alkoholer (f. eks. methanol, butanol), aminer (f. eks. ethanolamin, dimethylformamid) og vand; bære-stoffer, sâsom naturlige stenmel (f. eks. kaoliner, 1er-arter, talkum, kridt) og syntetiske stenmel (f. eks. h0jdispers kiselsyre, silicater); emulgeringsmidler, 25 sâsom ikke-ionogene og anioniske emulgatorer (f. eks.For the preparation of directly sprayable solutions, emulsions, pastes and oil dispersions, medium to high boiling point mineral fractions such as Petroleum or diesel oil, in addition coal oils, etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aliphatic, hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alcohols (e.g. methanol, butanol), amines (e.g. ethanolamine, dimethylformamide) and water; carriers, such as natural stone flour (e.g. kaolin, 1er species, talc, chalk) and synthetic stone flour (e.g., high-dispersion silicic acid, silicates); emulsifiers, such as nonionic and anionic emulsifiers (e.g.

polyoxyethylen-fedtalkohol-ether, alkylsulfonater og arylsulfonater) og dispergeringsmidler, sâsom lignin, sulfitaffaldslud og methylcellulose, i betragtning.polyoxyethylene fatty alcohol ether, alkyl sulfonates and arylsulfonates) and dispersants, such as lignin, sulfite waste liquor and methyl cellulose.

30 Formuleringerne indeholder i almindelighed mellem 0,1 og 95 vægt-% aktivt stof, fortrinsvis mellem 0,5 og 90%.The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.

Midler, som indeholder forbindelserne if0lge opfindelsen, kan ogsâ i disse anvendelsesformer foreligge sammen-35 blandet med andre aktive stoffer, f.eks. herbicider, insekticider, vækstregulerende midler og fungicider eller sammen med g0dningsmidler.Agents containing the compounds of the invention may also be present in these applications in admixture with other active substances, e.g. herbicides, insecticides, growth regulators and fungicides or together with fertilizers.

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1717

For anvendelsestiden gælder, at anvendelsen af de aktive stoffer if0lge opfindelsen skal foretages i et gunstigt tidsrum, hvis n0jagtige position retter sig efter de geografiske, klimatisk og végétative fænomener.For the period of use, the use of the active substances according to the invention must be carried out for a favorable period of time, the exact position of which aligns with the geographical, climatic and vegetative phenomena.

5 I de f01gende eksempler angives virkninger af stoffeme if01ge opfindelsen sont vækstregulatorer.5 In the following examples, effects of the substances according to the invention are indicated by healthy growth regulators.

Eksempel 2 10Example 2 10

Til unders0gelse af den biologiske aktivitet af de nye forbindelser gennemf0rte man fors0g i drivhus. Derved sâede man fors0gsplanterne under anvendelse af t0rvekul-tursubstrat, som var forsynet tilstrækkeligt med nærings-15 stoffer, i formstofbeholdere med en diameter pâ 12,5 cm. Anvendelsen af de aktive stoffer foregâr i vandig opl0sning eller dispersion i forskellige anvendte mængder pâ jordbunden pâ sâningsdagen. Stofferne blev derpâ spr0jtet direkte pâ jordoverfladen. I væksttiden pâ 18 20 dage udviste de planter, der var behandlet med de midler, som indeholder forbindelserne if0lge opfindelsen, i sammenligning med den ubehandlede blindpr0ve en tydeligt r ingéré længdevækst, hvilket kunne bekraeftes ved efterf0lgende længdemâlinger. Herved mâlte man 100 plan-25 ter i hver behandlingsrække.To study the biological activity of the new compounds, experiments were carried out in greenhouses. The test plants were thus seeded using peat culture substrate, which was adequately supplied with nutrients, in plastic containers with a diameter of 12.5 cm. The use of the active substances takes place in aqueous solution or dispersion in different amounts of soil applied on the sowing day. The substances were then sprayed directly onto the soil surface. During the growth period of 18 to 20 days, the plants treated with the agents containing the compounds of the invention, in comparison with the untreated blank, exhibited a clear longitudinal growth, which could be confirmed by subsequent length measurements. This measured 100 plants in each treatment series.

Det kendte aktive stof 2-chlorethyl-trimethyl-ammonium-chlorid (A) udviste for nogle planter og mængder en ringéré virkning (resultater: se tabel 3-5) 30 35 18The known active substance 2-chloroethyl trimethyl-ammonium chloride (A) showed a poor effect for some plants and amounts (results: see Table 3-5).

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Tabel 3 - Pâvirkning pâ længdevæksten af hvedeTable 3 - Impact on longitudinal growth of wheat

Aktivt stof Anvendt mængde Planteh0jde nr. kg/ha cm relativ 5 -^-Active substance Quantity of plant height no. Kg / ha cm relative 5 - ^ -

Kontrol (ubehandlet) - 29,5 100 A 3,0 21,1 71,5 12.0 19,3 65,4 10 - 7 3,0 25,5 86,4 12.0 17,0 57,6 15Control (untreated) - 29.5 100 A 3.0 21.1 71.5 12.0 19.3 65.4 10 - 7 3.0 25.5 86.4 12.0 17.0 57.6 15

Tabel 4 - Pâvirkning pà længdevæksten af byg 20 Aktivt stof Anvendt mængde Planteh0jde nr. kg/ha cm relativTable 4 - Effect on the length growth of barley 20 Active substance Applied amount Plant height no. Kg / ha cm relative

Kontrol (ubehandlet) - 28,5 100 25 A 3,0 23,3 81,8 12.0 21,5 75,4 19 3,0 23,5 82,5 12.0 20,5 71,9 30 -—---- 1 3,0 23,5 82,5 12.0 20,0 70,2 35Control (Untreated) - 28.5 100 25 A 3.0 23.3 81.8 12.0 21.5 75.4 19 3.0 23.5 82.5 12.0 20.5 71.9 30 -—--- - 1 3.0 23.5 82.5 12.0 20.0 70.2 35

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1919

Tabel 5 - Indflydelse pâ væksten af rapsTable 5 - Influence on the growth of rapeseed

Aktivt stof Anvendt mængde Planteh0jde nr. kg/ha cm relativ 5 -Active substance Quantity of plant height no. Kg / ha cm relative 5 -

Kontrol - 16,0 100 A 3,0 16,0 100 12,0 16,0 100 10 --- 7 3,0 15,0 93,8 12.0 10,5 65,6 19 3,0 15,0 93,8 15 12,0 11,5 71,9 23 3,0 15,0 93,8 12.0 12,0 75,0 20 21 3,0 15,0 93,8 12.0 12,0 75,0Control - 16.0 100 A 3.0 16.0 100 12.0 16.0 100 10 --- 7 3.0 15.0 93.8 12.0 10.5 65.6 19 3.0 15.0 93 , 8 15 12.0 11.5 71.9 23 3.0 15.0 93.8 12.0 12.0 75.0 20 21 3.0 15.0 93.8 12.0 12.0 75.0

Eksempel 3 25Example 3 25

Man blander 90 vægtdele af forbindelsen 3 med 10 vægtdele N-methyl-a-pyrrolidon og opnâr en opl0sning, der er egnet til anvendelse i form af meget smâ dràber.90 parts by weight of compound 3 are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution suitable for use in very small droplets is obtained.

30 Eksempel 4 20 vægtdele af forbindelsen 4 opl0ses i en blanding, der bestâr af 80 vægtdele xylen, 10 vægtdele af tillejrings-produktet af 8 til 10 mol ethylenoxid til 1 mol oliesyre- 35 N-mono-ethanolamid, 5 vægtdele calciumsalt af dode-cylbenzensulfonsyre og 5 vægtdele af tillejringsproduktet af 40 mol ethylenoxid til 1 mol ricinusolie. Ved 20Example 4 20 parts by weight of compound 4 are dissolved in a mixture consisting of 80 parts by weight xylene, 10 parts by weight of the preparation product of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid 35 N-mono-ethanolamide, 5 parts by weight calcium salt of cylbenzenesulfonic acid and 5 parts by weight of the preparation product of 40 moles of ethylene oxide to 1 mole of castor oil. At 20

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udhældning og fin fordeling af opl0sningen i 100 000 vægtdele vand opnâr man en vandig dispersion, der inde-holder 0,02 vægt-% aktivt stof.pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of active substance is obtained.

5 Eksempel 5 20 vægtdele af forbindelsen 3 opl0ses i en blanding, der bestèr af 40 vægtdele cyclohexanon, 30 vægtdele isobuta-nol, 20 vægtdele af tillej ringsproduktet af 7 mol ethy-10 lenoxid til 1 mol isooctylphenyl og 10 vægtdele af tille j ringsproduktet af 40 mol ethylenoxid til 1 mol rici-nusolie. Ved udhældning og fin fordeling af opl0sningen i 100 000 vægtdele vand opnâr man en vandig dispersion, der indeholder 0,02 vægt-% af det aktive stof.Example 5 20 parts by weight of compound 3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the product of 7 moles of ethylene oxide to 1 mole of isooctylphenyl and 10 parts by weight of the product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

1515

Eksempel 6 20 vægtdele af forbindelsen 4 opl0ses i en blanding, der bestâr af 25 vægtdele cyclohexanol, 65 vægtdele af en 20 mineraloliefraktion med kogepunkt 210 til 280 °C og 10 vægtdele af tillejringsproduktet af 40 mol ethylenoxid til 1 mol ricinusolie. Ved udhældning og fin fordeling af opl0sningen i 100 000 vægtdele vand opnâr man en vandig dispersion, der indeholder 0,02 vægt-% af det aktive 25 stof.EXAMPLE 6 20 parts by weight of compound 4 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a 20 mineral oil fraction of boiling point 210 to 280 ° C and 10 parts by weight of the preparation product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Eksempel 7 20 vægtdele af det aktive stof 5 blandes godt med 3 vægt-30 dele af natriumsaltet af diisobutylnaphthalen-a- sulfonsyre, 17 vægtdele af natriumsaltet af en lignin-sulfonsyre af en sulfitaffaldslud og 60 vægtdele pulver-formig kiselsyregel og formales i en hammerm011e. Ved fin formaling af blandingen i 20 000 vægtdele vand opnâr man 35 en spr0jtevæske, der indeholder 0,1 vægt-% af det aktive stof.Example 7 20 parts by weight of the active substance 5 are well mixed with 3 parts by weight 30 parts of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid of a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer silica . Fine grinding of the mixture in 20,000 parts by weight of water gives 35 a spray liquid containing 0.1% by weight of the active substance.

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2121

Eksempel 8 3 vægtdele af forbindelsen 3 blandes grundigt med 97 vægtdele findelt kaolin. Man opnâr pâ denne mâde et 5 pudringsmiddel, der indeholder 3 vægt-% af det aktive stof.Example 8 3 parts by weight of compound 3 are thoroughly mixed with 97 parts by weight of finely divided kaolin. In this way, a powdering agent containing 3% by weight of the active substance is obtained.

Eksempel 9 10 30 vægtdele af forbindelsen 4 blandes grundigt med en blanding af 92 vægtdele pulverformig kiselsyregel og 8 vægtdele paraffinolie, der blev spr0jtet pâ overfladen af denne kiselsyregel. Pâ denne mâde opnâs et præparat af det aktive stof med god adhæsionsevne.EXAMPLE 9 30 parts by weight of Compound 4 are thoroughly mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. In this way, a preparation of the active substance with good adhesiveness is obtained.

1515

Eksempel 10 40 vægtdele af det aktive stof 3 blandes grundigt med 10 dele natriumsalt af et phenolsulfonsyre-urinstof-formal-20 dehyd-kondensat, 2 dele kiselgel og 48 dele vand. Man opnâr en stabil, vandig dispersion. Ved fortynding med 100 000 vægtdele vand opnâr man en vandig dispersion, der indeholder 0,04 vægt-% aktivt stof.Example 10 40 parts by weight of the active substance 3 are thoroughly mixed with 10 parts of sodium salt of a phenolic sulfonic acid urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion containing 0.04% by weight of active substance.

25 Eksempel 11 20 dele af det aktive stof 4 blandes grundigt med 2 dele calciumsalt af dodecylbenzensulfonsyre, 8 dele fedtalko-hol-polyglycolether, 2 dele natriumsalt af et phenolsul-30 fonsyre-urinstof-formaldehyd-kondensat og 68 dele af en paraffinsk mineralolie. Man opnâr en stabil, olieagtig dispersion.Example 11 20 parts of the active substance 4 are thoroughly mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolic sulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable, oily dispersion is obtained.

3535

Claims

DK 157363 BP atent requirements: r-azolyl alcohols for regulating plant growth, ke n-5 characterized by having the formula: R1 - CH - CH2 - CH - R * III OH Az 10 wherein R1 and R2 which may be the same or different is alkyl of up to 5 C atoms, cycloalkyl, furanyl, thiophenyl, pyridyl, naphthyl or phenyl, whereby the phenyl residue may be substituted by halogen, alkyl, alkoxy, alkenyloxy, hydroxy, nitro, trifluoromethyl, or R be biphenyl and Az is an imidazol-1-yl or 1,2,4-triazol-1-yl group. 20 25 30 35