DD145599A1 - MEANS FOR REGULATING PLANT GROWTH - Google Patents

Abstract

The invention relates to novel means of regulating the Plant growth, in particular to increase the fruit set at agricultural and horticultural crops. The invention » Corresponding means provide a chemical structure new type of growth regulatory active compounds, In particular, on the flowering, the flowering process and the Interacting sex determination, promoting the fruit neck that Yield, the fruit quality, the content content and the Shelf life of crops positively influence the Accelerate maturing process as well as potencies Senescence influence, side shoot and Geiztriebhemmung feature. They are characterized by a content of compounds of general formula I in which r "1, r2, r3 and r4 are aliphatic, cycloaliphatic or aromatic radicals, which may be optionally also substituted, n the integers 0 to 3 and X are inorganic or organic acids or Quarters. Slide in the invention mentioned substances of general formula I are depending on Use in drug concentrations of 0.01 ppm to 10,000 ppm applied, expediently in the for sur sur biological process control usual preparation or Application forms such as solutions, emulsions, suspensions, powders, Pastes or granules, These formulations are known in the art Manufactured way.

Description

Means for regulating plant growth

Field of application of the invention

The invention relates to new gowns for regulating plant growth, in particular for increasing the fruit set in agricultural and horticultural crops.

Characteristic of the known solutions

Due to the current state of the art, it is possible to specifically intervene in the plant growth and development processes with already known artificial substances

Artificial regulators of plant metabolism and growth may be effective on a wide variety of receptors and may vary depending on the stage of development of the plants or plant parts or organo, the mode of administration, the time of application, and the mode of administration of the active ingredient Trigger reactions, resulting in a variety of possible applications »

It is known that substances with different chemical structure on the flower formation (DT Patent 2 110 ?? 3 _S CH Patent 4O38 _s DDIHPatont I69 490), the Gächlechtsdeterraination bsi cucumber (US Patent 3? 3 55S ₉ DDR-Fatoixt 184 324 'DDR patent' Ί69 490j DT Pat. No. 2 217 896) or the fruit set and yield (DT Patsnt 2 21-896, DT patent 2 400 454 _S US patent 18 845i CH patent 403S ₃ , DDR patent I69 490) influencing acting

~ ₂ ' ^: ~ fts is!

With regard to the chemical structure, the substances according to the invention represent a new type of growth-regulatory active compounds which, depending on the form of application, have a multiplicity of effects and in practice permit numerous application possibilities.

Object of the invention

The use of suitable means to regulate metabolic and growth processes in plants pursues the goal of increasing the yields of agricultural and horticultural crops, or to make them stable and to positively influence the quality of the harvested products. "The aim is also to reduce the burden on the environment reduce chemical substances and achieve a high economic effect through minimal effort »

Explanation of the essence of the invention

The invention relates to the use of active substances, which are tolerated in a large concentration range of a variety of crops and regulate the plant metabolism and the growth act. It has been found that substances of the general formula I.

R- (CH ₂ ) η CH / - N R ^{4 (} · -Χ \ \ R ²

1 in the R for aryl, substituted aryl, cyclohexyl, alkyl or

Pyridylj

R is alkyl which may optionally be substituted by aryl or cycloalkyl, aryl or cycloalkyl,

ir is hydrogen, methyl or ethyl,

2 for cycloalkyl or alkyl, the latter optionally being substituted by aryl, cycloalkyl> piperidyl, pyridyl, hydroxy, amino or acylamino, η is the integers 0 to 3

and X is HCl, oxalic acid, methyl iodide, dimethyl sulfate or E SO,

have a variety of growth characteristics, but in particular have an influence on flowering, the flowering process, sex deterioration, promote fruit set, positively influence the yield, fruit quality, content content and shelf life of harvested products, accelerate the ripening process and over potencies for Seneszenzbeeinflussung "S.eitentriebbildung and epicormic shoot inhibiting feature" the novel part of the compounds are prepared by known methods, for _e B ', by reacting the corresponding ketones of the general formula

- (CH ₂ ) _f

.CO

with amines of the general formula H_N - R. to ship *! Bases which reduce to the "invention-containing substances and which may optionally alkylate and quaternize them"

Another way to represent is the implementation of amines of the general formula

^R 1

CK - HK ₀

with corresponding ketones or aldehydes to Schiff bases, which are converted by reduction into the substances according to the invention

and then optionally alkylated or quaternized »

From the above applications, the advantage of compounds of formula I is obvious, namely that they can be used in a variety of ways on a variety of crops to regulate the metabolism and growth processes * Decisive for the intended effect, especially concentration or amount of the administered drug and the longitudinal development of plants or plant parts or organs *

The application of the substances, according to formula I is advantageously carried out in the usual means for biological process control preparation or * application forms such as solutions, emulsions, suspensions, concentrates, with the addition of liquid and / or solid carriers bsw · diluents usually with the addition of surface-active Prepares substances and other formulation aids and can be diluted with water for use »The forms of application depend on the intended use. You have a fine one in any case. To ensure distribution of the active substances. The preparations are produced in a conventional manner by mixing "or grinding processes' · Also preparations in the form of powders or granules, pastes ₅ are possible"

The substances of the general formula I mentioned in the invention are used, depending on the intended use, in active ingredient concentrations of from 0.01 ppm to 10 000 ppm (10 % to 10 ° C./S)

The following examples illustrate the invention without limiting it. The synthesized compounds and their physical data are listed in Table 1

Example "1 N ^M cyclohexyl-1,3" diphenylpropylamine "" 2 '' hydrochloride

a) 42.0 g (0 ₈ 2 MoI) of 1,3-diphenylpropanone = - 2 are rait 19 * 8 g (0.2 mol) of cyclohexylamine and 200 ml of xylene with the interposition of a water for about 1 h under reflux boiled It 3.4 ml of water are separated off. The xylene is then distilled off under reduced pressure, and the residue is taken up in methanol and hydrogenated under normal pressure after addition of a suitable hydrogenation catalyst. The hydrogen uptake is 4.2 l. The catalyst is separated off and the methanol is removed distilled off small residue. The methanolischo residue is now made weakly acidic with HCl gas and then treated with ether "is obtained 55» S g K-cyclohexyl ~ 1 _i 3-diphcnylpropylamin '~ 2 Hydrochloride _S which after recrystallization from alcohol / ether, an F »From 207/209 ° C shows»

b) 42 _S 2 g (Oj2 mol) of 1,3-diphenylpropylamine ~ 2 v / erden treated with 19 _S 6 g (O ₄ 2 mol) of cyclohexanone and 250 ml of xylene in the same manner v / ie described under a) after distilling off the xylene under vacuum, the residue is Schiff's base "is hydrogenated and worked up as described under a)." This results in about 57 g X'ohes N-cyclo-hexyl-1,3 "" diphenylpropylamine-2 hydrochloride _t that melts after recrystallization at 207/209 ° C,

N-Möthyl-l '. ^T ~ cyqlohcxyl ~ 1,3 ~ ^- diphenylpropylamine ~ 2- ⁱ hydrochloride

g (0 _¥ 3 mol) of N-cyclohexyl-1'-diph'aurylpropylassin ^ are dissolved in 400 ial methanol, 0 g of 30 #iger formaldehyde »LÖDung and 40 g Ranoy nickel vorsetztx and under normal pressure with hydrogen reduced after boendex ^'1 Wasserstoffaufnahrae is separated from the catalyst and the solvent ABDT under vacuum; stilliort * the residue is dissolved in a little ethanol ;, abon> nit HCl gas. sour and with the double

Volume Ether added, "gives about 66 g of crude K-methyl-N-cyclohexyl-1 _f 3-diphenylpi" opyIamin ~ 2-hydrochloride ₉ after recrystallization from alcohol / ether has a mp of 183/184 ° Cβ

N, N _, N-dimethyl-N-cyclohexyl-1- _i- 3-diphenylpropyl-ammonium-2-iodide 30-g (0 * 1 mol) N-methyl-K-cyclohexyl-1,3-o-diphenylpropylamine with 14 ₉ 5 g (0 _s 1 mol) of methyl iodide in 100 ml of acetone refluxed for about 2 hours »With good cooling, 25 g of Ainmoniurasalzes precipitate in almost pure form with a F. of 202/204 ° C.

N _t N-DiHet-hyal-1-cyclohexyl "1 _i 3 '- diphenylpropylafflmonium" -2 ™ sulfate 30s? g (0 _s 1 mol) of N-methyl-N-cyclohexyl-1,3'-diphenylpropylanine-2 are dissolved in 100 ml of ethanol and added dropwise with stirring to 13 g (0 _s 1 mol) of dimethyl sulfate at room temperature stirred for a few hours and allowed to stand overnight in the refrigerator »The precipitated hethosulfate is filtered off with suction5 washed with ether and dried. 35 g is obtained about _a crude _SAL2} which melts after recrystallization from alcohol / ether at 145 / 14-3 ° C · ...

N- (p-methoxybenzyl) "= '2 _s 4-" diniethylpentylamine "~ 3"" ⁿ yd. Hydrochloride 27.2" g (0 _$ 2 moles) of anisaldehyde are mixed with 23s, 0 g (0.2 mol) of 2 _i 4-Dimothylp6ntylamln-3 together dissolved in 25Ο ml of xylene and h under Zv / ischenschaltung a water separator 4 is boiled under reflux. There are deposited ca »1 _S 7 ml of water from" the xylene is distilled off under vacuum and the residue after recording in Hydrogenation of methanol and the addition of the catalyst After separation of the catalyst, the solvent is "off-tartarated" by treatment with HC1 gas. The base obtained as residue is converted into the hydrochloride ₍ which is added)

Addition of ether crystallizes to yield 15.0 g of crude N ~ (p "" methoxybenzyl) ~ 2 s ^ dimethyl pentylatnine-3 "" -hydrochloride id., After recrystallization from isopropanol / Xther

F. of 218 C owns

H ~ (1'-Cyclohexylp? Opyl ~ 2 ^t ) ""'"" phenylpropylafflin-2 ~ hydrochloride 26.8 g (0.2 mol) of 1-phenylpropanone ~2 and 28y3 g (0.2 mol) of 1-cyclohexylpropylamine » The mixture is dissolved in 50 ml of methanol and heated for about 20 minutes to 40 ° C. Subsequently, 3% of methanol and a suitable hydrogenation catalyst are added and then hydrogenated under normal pressure The residue is suspended in 100 ml of water and slightly acidified with concentrated hydrochloric acid. After cooling in the refrigerator, about 43 g of crude K ( ^{/ s} "cyclohexylpropyl" 2 ^! ) '1 "-phenylpropylamine are obtained * -2 * - Hydrochloride, which after recrystallization from aqueous methanol, an F * of 215/218 C showed

N'-Cyclohex.yl-i - ^ - pyridylpropylarjin '- ^ -' hydrochioride 2? F2 g (0.2 mol) -Pyridylpropylamin-2, 19.6 g (0 _s 2 mol) of cyclohexanone and 250 ml of xylene are under Intermediate connection of a water separator boiled for about 1 h under reflux. The xylene is then distilled off under reduced pressure and the resulting Schiff base is taken up in methanol and hydrogenated under normal pressure after addition of a suitable hydrogenation catalyst. The catalyst is separated off, the solution is acidified with concentrated HCl and then brought to dryness in vacuo. The solid residue is dissolved in Xtha. dissolved nol warm and after dera cooling with ether presetted The precipitated N "-Cyclohexyl ™ Ή-pyridyl-propylamine ^ -hyärochloria is filtered off with suction, washed and dried» Hon receives 44- g crystalline substance, which after recrystallization from ethanol / Athor a F «Possessed from 204/206 ° C«,

i% ß

Effect of N-methyl ^ = N ~ (1 _i '3 "" äiphenylpi-opyl-2) "cyclohexylarnin"' methosulfate (order "no. 12) on the cucumber at Geschiechtsdetermination" variety "Eve"

The plants were grown in the greenhouse and sprayed to drip point in the 2- to A-leaf stage with the spray. At an active ingredient concentration of 10 * 000 ppm (10%), the number of female flowers was significantly increased * while at the same time shortening the shoot length (Table 2) »

Promoting fruit set by N-methyl-N- (1,3-diphenylpropyl-2-cyclohexylarainraetbosulfate (current Kr 12) in tomato, variety Grit

At concentrations of 10 and 100 ppm sprayed on the inflorescence at the time of flowering, tomatoes in the greenhouse (decapitated on 2 inflorescences) showed an increase in fruit number and yield (Table 3) *

Promotion of the fruit batch by N ~ methyl ~ i'I ~ 1 _f 3 "" diphenylpropyl ~ 2) -cyclohexylaiainraethosulfate (no. "12) in cucumber, variety" Spotresisting "

Boi application of the active substance in concentrations of 500 to 5 * 000 ppm in cucumbers in Folienzolt, applied at 2-4 ~ leaf stage, was to achieve a substantial increase in the number of red-eared fruits and the total yield (Table 4-) ₀

Example 11

Promotion of fruit set by N ~ methyl ~ N- ^> (1 _e 3 '~ diphenylprOpyl »2) ™ cyclohexylarainmethosulfat (Ifd * Nr * 12) in tomatoes ^ variety" Harzfeuer "

In the field trial (20 plants per plot, '6 repetitions), a significant increase in the yield of N-methyl-> N- (1,3-diphenyl-propyl-2) cyclohexylamine methosulfate was observed.

Fruit number and yield of tomatoes a _s wherein the average fruit weight was- not affected * The plants were decapitated at 2 inflorescences "The application was carried out on the whole plant to the start of flowering of each of the two inflorescences (Table 5) *

Promotion of fruit set by N-methyl-N "(1,3" * diphenylpropyl-2) ~ cyclohexylamine hydrochloride (Ifde Kr · 11) in tomato, variety "Harzfeuer"

In field experiments (20 plants per plot _t 6 repetitions) was when using L ^v M-! Ethyl-N- (1 _t 3 ~ diphenyl-propyl-2) -cyclo · hexylamin hydrochloride, a substantial increase in the fruit count and increase in the The plants had been deciduous on 2 inflorescences. The application was made to the whole plant at the beginning of flowering of each of the two bleeding levels table 6).

The youngsters wax turnst e st

Cresses of the winter wheat variety "Mironowskaja 808 ^u are pre-swollen in the test solution for 24 hours and germinated at 25 ° C." After one day, the seedlings are transferred to hydroponics and their shoot length, development and anomalies are measured or scored * (Table 7) "

Leaf also test

3 weeks old bean seedlings (Phaseolus vulgaris), processed into cuttings with two primary leaves. Application is by dipping the leaves in the test solution. "The criterion of effect after 6 days is the number of fallen or withered leaves compared to un-

P acted control, The table ° shows the results of the testing,

Sikkation / defoliation in cotton

From cotton plants (Gossypiuia hirsutum) cultivated in the greenhouse, the cotyledons are dipped into the test solution in the 2-leaf stage. Bach 12 days is scored for siccation (1 = weak, 2 κ medium} 3 = strong) and defoliation of the cotyledons «(Table 9).

in the R for aryl, substituted aryl "cyclohexyl", alkyl or pyridyl _t

R is alkyl which may optionally be substituted by aryl or cycloalkyl _s aryl or cycloalkyl

3 ..

ir for Wasserstoffj methyl or ethyl _t R for oder.Alkyl cycloalkyl "may be substituted with the latter optionally substituted by aryl," cycloalkyl Piperydyl _s, pyridyl, hydroxy _s' is amino or acylamino, η for the integers O to 3 ^an d X is HCl are, oxalic acid, 'methyl j iodide, dimethyl sulfate or _H? SO. ,, and used in admixture with conventional carriers and fillers ^ Hili'sstoffen or solvents v / _fi erae'n

2 "means zui · Seguli.erung of the plant growth * ,, characterized _f to act on the Geschlechtsdeiennination and fruit set in agricultural and horticultural crops"'

Si!

Table 1

R ¹ η E ¹ - (CH ₂ ) _n \ CH _ / - K \ R ³ • X L ^C 6 ^H 5 " R ^{/ + GI!} 3 -CH ₂ -CH ^C 6 ^H 11 X Fp ⁰ C R ^ R ^ ^C 6 ^H ₅ ~ -CH - CH- 2 1 CH ₃ ^C 6 ^H 11 CgH ₅ 1 R ² R ³ CgH - CH ₂ -CHg ^CH 3 CgH ₁₁ (( HCl 157-161 ^C 6 ^H 5 1 CH ₂ - CH-CH "I 1 C ₅ H ₉ HCl 197-198 ^C 6 ^H 5 1 CH ₃ H ^C 6 ^H 11 CH- OH CH HCl 208 - 212 Lfdo CH ₃ H C ₂ H ₅ Pipericlyl "· No. ₉ - CgH ₅ 1 rs η _Λ «1Τ C ₆ H ₅ -Ch ₂ H -CH ₂ -CH ^C 6 ^H 11 CgH ₁₁ HCl 215 - 218 1 1 CH ^C 6 ^H 11 2 ^{C 6K} 5 1 CH H C ₆ H ₅ -CH ₂ -CH- 13 HCl 18? - 191 3 e ^C 6 ^H 11 C ₆ H ₅ 0 CgH ₅ -CH ₂ CH ₃ C ₆ H ₁₁ ^H 2 ^C 2 ° 4 147 - Ή9 4 Ah CgH ₅ 1 CH ₃ 6 5 CgH ₁₁ HCl 202 - 2.O5 5 (CH) CH- C ₆ H ₅ 1 r ΐτ ».ρ w CgH ₅ Ch ₂ CH HCl I85-190 6 ^C 6 ^H 5 1 124-126 C ₆ H ₅ -CH ₂ H n-Cgl! 7 ^C 6 ^H 5 1 C ₆ H ₅ -CH ₂ CH ₃ CH J 202-204 HS 1 CgH ₁₁ HCl 183 ~ 184 8th CgH ₅ 1 CgH ₅ ^ CHg CB ₃ ' ^H 3 ^ 2 ⁸⁰ ^ - 143 - 145 9 CgH ₅ 1 CgH ₅ -CH ₂ CH ₃ HCl 178 - 181 CgH ₅ 1 ft xs «./"merk 65 2 CH ₃ HCl 226 ~ 229 10 CgH ₅ 1 CgH ₅ -CH ₂ K HCl 186 - I89 11 C ₆ H ₅ 2 Γ * Τϊ Λ »XJ CgH-CH K KCl 169 -. i? i 12 ^C 6 ^H 5 2 H HCl 146 - 148 13 CgH ₅ 1 CH ₃ H HCl 153-155 14 CgH _n 2 C ₂ H ₅ H KCl 243 - 244 15 ^C 6 ^H 5 1 CgH ₅ -CH ₂ H HCl 203 »206 16 CgH ₅ H 17 CgH ₅ -CH ₂ H 18 19 20.

Ser. R-No.

Fp ⁰ C

1 C ₆ H ₅ -CH ₂

H CH ₂ -CH ₂ OH HCX 99-101

H 4CU 0-C ₆ H ₂ ~ CH ₂ HCl 216-213

23 C ₆ H ₅

HCl 121-123

OH

24 CgH ₁ - 3 CH H H HCl HCl HCl 132-135 ^H 2 ^C 1 / 2HpS 2 ° 4 " ^{! 53} - 24 ' 25 <^ Η _Κ 6 5 1 H ^C 6 ^H 5 ~ ^(C V4 -CH HCl CH HCl I62 - I63 H ₂ C -CH _{? 2} «CE rfl, Ί28 2. 4 0, 125 V 26 C ₆ H _U -: 1 C ₆ H-CH H CxipCii V ₁ UlI ^ ρ HCl 186 - 188 cL HCl 218 HCl 186 ~> ^ 5 «- 12 27 ^C 6 ^H 11 O CH H ^C 6 ^H 11 HCl HCl 260 - 261 - 13: - 12 ' 28 29 4-CH ₃ -C ₆ II ₄ pyridyl- (2) - O 1 ^C 6 ^H 11 H H ^C 6 ^H 11 ^C 6 ^H 11 HCl HCl 264 - 266 204 ~ 206 - 16: -. 22 · ~ 18: 30 C ₆ H ₁₁ 1 C ₆ H ₁₁ -CH ₂ H -CH-HCl 141 - 144 CH ₃ 31 32 6 5 1 1 C ₆ H ₅ -CH ₂ ^C 6 ^H 5 " ^CH ?" HC ₂ H ₅ ^C 6 ^H 11 207-209 203-206 33 ^C 6 ^H 5 O ^C 6 ^H 11 H C ₆ H ₁₁ 277-282 34- ^ CH ₃ -C ₆ H ₄ - O ^C 6 ^H 11 H ^C 6 ^H 11 264 - 266 35 4 "CH _r -C, -H," ρ 5 ° 4 • O H ^C 6 ^H 11 247 - 249 36 <U 6 5 1 CH H Pyridyl (4) -CH- 2HCl 244 CH ₃ 3? 38 ^C 6% 3 3 c! i ³ H H -NH (CO) CII (CH ₃₎ H ₂ C 39 40 C ₆ H ⁵ 3 CH ₃ ^CIi 3 H H 41 42 4-3 ^C 6 ^H 5. (CHO-CH C-VH ₁ - 6 j? 3 o C ₆ H ₅ (CH ₂ ) ₅ (CHy ₂ -CH H tr H 4-CH ₃ OC ₆ H ₄

Tabellejg

Effect of IV-methyl-N-cis 3 "* diphenyl-propyl ~ 2) -cyclohexylamine * methosulphate on the sexual maturation of cucumbers _t » Eva »

Act of fec ^; i Number of female flowers

in the relative to the unbeh. relative to

Spray mixture control unbeh "control

10000 ppm 180 8?

1000 ppm 125

Promotion of fruit set by N ~ methyl-N ~ (1,3-diphenylpropyl-2) -cyclohexylamine-niethosulfat in tomatoes, variety "Grit",

Impact offensive Number of fruits Yield relative in the relative to to the unbeh " spray mixture unbeh "control control 100 ppm 106 126 10 ppm 136 129 Table 4

Promotion of the fruit batch by N ~ methyl-lT ~ (1 ₉ 3 * ~ d.iphenylpropyl * -2) ~ cyclohexylarain ~ methosulfate in cucumber _$ variety "Spotresisting'O

Active substance concentration »Number of fruits Yield relative

in the relative to the unbeh _β

Spray mixture unbefcu control control

5000 ppm 126 12?

1000 ppm 129 139

500 ppm 130 I30

- 5 # 1 h

Sefef

TabjeIj-e J?

Requirement of fruit set by N-methyl "N- (I, 3-diphenylpropyl-2) -cyclohexylamine methosulfate in tomatoes, variety" Harzfeuer "»

· ^{Wirkstoffkonz:} in the fuel broth Number of fruits relative to the unbehv Kontr * Yield \ relative ZeunbeheKontr medium fruit ™ weight relative ₆ z "uncontrolled" 50 ppm 10 ppm 5 ppm 119 118 121 112 129 11? 9Ψ 103 98 Table 6

Promotion of fruit set by H-methyl-N- (1,3-diphenyl-propylc-fi) -cyclohexylamine hydrochloride in tomato, variety Harzfeuer,

Wirkstoffkonz in the Sprit2brühe

50 ppm 10 ppm

1 ppm

Number of fruits yield

relative to the relative

unbehe contra ucunbeh.contr

medium fruit 'weight' relative 'ζ »untreated control *

97 11.8 118 114

119

133 • 126 126

111 106 106 111

9% for »

IfcL No. according to Table 1 Concentration of tissue ~% Length increase in % 11 10 " ¹ 10" ² - 71 - 10 13 1O ~ ¹ - 43 14 10 ¹ - 68. ΙΟ "* ² - 21 15 -o- ¹ - 86 10 "* ² - 60

16 1?

19 27

28 25 42

10th

10 * 10 *

10 "10"

10 '

1ο ¹

10 '10'

"" ¹

* " ¹

" ¹

-

~ 77

- 20

- 64

- 51

- 66

- 25

- 86

- 40

- 49

- 15

gabelle 8

Defoaming bz-v / _e sikkierende potencies of the compositions of the invention

Ifde Nr _e according to Table 1

16

17

28

24

38

39

40

25 30

41 42

concentration

1ο ¹ -io ^c

10 ^c 10

10 ^C 10

10 ^C 10 "

10

10 '10

10 ^C 10 "

10

10

"" ¹

Defoliation of leaves (%) Sikkation (bon door) '* 70 70 60 60 1 2 2 1 90 90 3 1 100 • 100 3 2 40 3 100. 100 3 3 SO 80 1 1 60 30 2 1 100 3 90 2

7-

s

weak siccation medium siccation strong siccation

TabelIs 9

lfdt Nt, according to concentration Sikkation Table 1 Gew ^ - (Bunitur)

defoliation

$ to control

10 "2 1

Claims (1)

claim 1 means for regulating plant growth, characterized in that they contain compounds of general formula I, E ¹ - (CH _£ ) _a .CH - H ⁶ X> ι, R ²