CS239422B1 - Substituted benzothiazolium salts and a process for their preparation - Google Patents
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Abstract
Vynález rieSi spfisob přípravy nových látok 2-alkyltio-3-alkylbenzotiazolových solí všeobecného vzorca I kde R znamená metyl, etyl, alyl, propargyl, izobutyl; R1 znamená vodík, metyl, etyl, alyl, etoxykarbonylmetyl, benzyl, dodecyl a X” znamená Br”, I”, HSO^, alebo CH^SO^, s tým, že keí X“ je I" tak R neznamená metyl· Podstata spOsobu přípravy látok podTa vynálezu spočívá,v tom, že deriváty 2- -benzotiazolíntionu reagujá s RX, kde R a X znamená to isté, ako vo vzorci I a v prostředí organických rozpúšťadiel, ako sú nitrometán, aceton, tetrahydrofurén, dimetylformamid. zmes dimetylformamidu a acetonu (3:1) alebo bez rozpúšťadla pri teplote 18 až 110 °C po dobu 30 minút až 24 hodin. Látky podTa vynálezu sú účinné ako stimulétory alebo inhibitory rastu rastlin.The invention solves the problems of preparing new substances of 2-alkylthio-3-alkylbenzothiazole salts of general formula I where R means methyl, ethyl, allyl, propargyl, isobutyl; R1 means hydrogen, methyl, ethyl, allyl, ethoxycarbonylmethyl, benzyl, dodecyl and X" means Br", I", HSO4, or CH2SO4, with the proviso that when X" is I" then R does not mean methyl. The essence of the method for preparing the substances according to the invention lies in the fact that the 2-benzothiazolinethione derivatives react with RX, where R and X mean the same as in formula I and in the environment of organic solvents such as nitromethane, acetone, tetrahydrofuran, dimethylformamide. a mixture of dimethylformamide and acetone (3:1) or without a solvent at a temperature of 18 to 110 °C for a period of 30 minutes to 24 hours. The substances according to the invention are effective as plant growth stimulants or inhibitors.
Description
239422 2
Vynález sa týká derivátov benzotiazóliových solí obecného vzorca I
kde B znamená metyl, etyl, alyl, propargyl, izobutyl, R1 znamená vodík, metyl, etyl, alyl, etoxykarbonylmetyl, benzyl, dodecyl a X“ znamená jód, bróm, hydrosulfát, metylsulfát, spfisobu ich přípravy a účinku ako sti-mulátorov a inhibítorov rastu rastlín.
Podrobný literárny prieskum bol uvedený v práci 2-alkoxykarbonylmetyltio-3-alkyl-benzotiazóliové soli a spfisob ich přípravy (Sutoris V., Sekerka V., Sohlerová R.: AO 233 443. Z uvedených zlúčenín bol syntetizovaný, rozdielnou metodikou a v nízkomvýtažku len 2-metyltio-3-metylbenzotiazóliumjodid (Fry D. J., Kendall J. D.: J. Chem.Soc. 1951, 1 716). Ostatně benzotiazóliová soli podl*a vynálezu nie sú v literatúre do-teraz popísané a Studiu ich biologickej účinnosti nebola věnovaná žiadna pozornost.
Podstata spfisobu přípravy látok podl'a vynálezu spočívá v tom, že deriváty 3—R1—2—-benzotiazolíntiónu vzorca II C=Sdi—r1 (II) kde r' znamená to isté ako vo vzorci I, reagujú s RX, kde R a X znamená to isté, ako vovzorci I v prostředí organických rozpúětadiel, ako sú nitrometán, aceton, tetra-hydrofurán, dimetylformamid, zmes dimetylformamidu a acetonu (3:1) alebo bez roz-púšťadla pri teplote 18 až 110 °C po dobu 30 minút až 24 hodin.
Uvedenú reakciu naznačuje nasledovná schéma: s". C=Slil — R1
+ RX c — s -dl - r1 kde R, R1 a X” je horeuvedené: Všeobecné postupy přípravy 2-alkyltio-3-alkylbenzotiazóliumhalogenidov, hydrosulfátova metylsulfátov. 3 239422 Přikladl 0,03 molu 3-alkyl-2-benzotiazolíntiónu sa rozpustilo v 15 »1 nitroaetánu a po přidaní0,035 molu příslušného alkylhalogenidu sa reakčná zaes nechala stať prl laboratórnejteplete 24 hodin. Vykrystalizovaný podlel sa odfiltroval a prenyl acetónoa. Příklad 2 K 0,03 aolu 3-alkyl-2-benxotiazolíntlónu sa přidalo 0,04 aolu alkylhalogenidu areakčná zaes sa zahrlevala 4 hodiny na teplotu 70 aš 80 °C. Po přidáni suchého acetonusa pevný podlel izoloval flltréclou. Příklad 3 0,03 aolu 3-alkylbenzotlazolíntiónu sa rozpustí v 15 aš 20 al nitroaetánu, acetonu,tetrahydrofurénu, diaetylforaaaidu alebo zaesl diaetylforaaaidu a acetonu (3:1), pridésa 0,04 aolu alkylhalogenidu a reakčná zaes sa zahrieva vo vodnoa kúpeli na 60 aš 75 °Cpo dobu 10 hodin. Příklad 4 0,03 aolu 2-alkyltio-3-alkylbensotiasóliuahalogenldu sa rozpustí v 50 al vody, roztoksa přefiltruje a pridé 5 %-ný prebytok KCIO^ rozpuštěného v 15 al vody. Z bleleho zákalusa vylúCi olejovltý podlel, ktorý stétia krystalizuje. Příklad 5 K 0,03 aolu 3-*alkyl-2-benzotiazolíntlónu sa pridé 4,4 g /0,035 aolu) dlaetylsulfétua reakčná zaes sa 30 alnút aš 1 hodinu zahrieva na 60 aš 110 °C. Po vychladnutí sa pridéaceton, pevný podlel sa odfiltruje a dobré preayje acetónoa. Příklad 6 0,03 nolu 3-alkyl-2-benzotlazollntlónu sa rozpustí v 15 al acetonu a po přidaní 4,4 g(0,035 nolu) dlaetylsulfétu sa reakčná zaes zahrieva na teplotu varu reakEnej snesl 2 aš3 hodiny. Po ochladení sa isoluje krystalický podlel. Příklad 7 0,03 nolu 3-alkyl-2-benzotiazollntiónu sa rozpustí v Í5 al tetrahydrofurénu a sa nieSanlasa prlkvapké 3,4 g (0,035 aolu) HgSO^. Vylúčené krystalické létka sa čistí kryStallséciouz etanolu.
Analogické postupy sa poušijú pre přípravu alkenyl, alkinyl, etoxykarbonylaetyl abenzyl derivátov. Výsledky elementérnej analýzy a fyzlkélnochenické konstanty syntetizovaných zlúčenlnpodTa vynálezu sú uvedené v tabuPke 1. 'h-NMR spektrá bolí naaerané na přístroji Tesla BS 487 A prl 80 IIHZ v deuterovanejtrifluoroctovej kyselině, vnútorný Standard hexanetyléndlsiloxán. Výsledky sú uvedenév tabuíke 2. 239422 4 Látky podfa vynálezu sú účinné ako stlmulátory a inhibitory rastu rastlln. Baštovétesty aa uskutečnili autorml modifikovanou metodou na objekte vika siata. Přiklad 8osvetruje spdsob testovania zlúčenin pódia vynálezu na stimulačnú a lnhiblčnú účinnost. Přiklade
Semená vlky slátej klíčili v Petriho miskách v termostate, v trne prl 25 °C. Klíčencepo 48-hodinovom raste sa exponovali v molárnyeh roztokoch benzotiazóliových soliach,obecného vzorea 1, kde B, r’ a X~ znamená to isté, Testovanie sa uskutečnilo v koncentračnej Skále 10~16 až JO“1 mol. dm~3 a po 24 hodinách inkubácle bol stanovený prlrastokpredlžovacleho rastu koreňov. Při každom stanoveni bol uskutečněný aj rastový efektv kontrolněj sérii.
Ako Standardy boli testované kyselina beta-lndolyloctová (IAA) a kyselina 2,4-di-chlórfenoxyoctová (2,4-0) a 2-chlóretyltrimetylamóniumchlorid (CCC). Výsledky stimulač-ného a inhiblčného účinku syntetizovaných zlúčenin pódia vynálezu sú uvedené v tabuTke 3. 5 239422 «ρ e-3
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Tabulka 2
’η-NMR chemické posuny (δ) benzotiazóliovýeh solí syntetizovaných podTa vynálezu číslo R R1 X“ I CH3 H HSO4 7,8 až 7,2 (ar, 4H, a); 2,66 (S-CH3, 3H, a) IX CH3 c»3 CH3SO4 7,8 až 7,2 (ar, 4H, b)j 3,78 (rf-CHp 3H, s)3,50 (CH3SO4, 3H, s)} 2,70 (S-CH3, 3H, s) III OT3 CH3 C1O4 7,8 až 7,2 (ar, 4H, a); 3,75 (N+-CH3, 3H, s)i2,67 (S-CH3, 3H, s) IV ch3 ch2ch=ch2 CH3SO4 7,8 až 7,2 (ar, 4H, a)j 5,5 (=CH, 1H, a); 5,0 (=CH2, 2H, b); 4,86 (N*-CH2, 2H, d); 2,71 (S-CH3, 3H, s) v CH3 ch2ch=ch2 J 7,9 až 7,2 (ar, 4H, a)j 5,6 (=CH, 1H, a){ 5,1 (=0¾. 2H, a); 4,88 (M+-CH2, 2H, d)j 2,73 (S-CH3, 3H, s) VI ch3 ch2cooc2h^ J 7,9 až 7,2 (ar, 4H, a)j 5,16 (N*-CH2, 2H, a);4,00 (0-CH2, 2H, q, J=7,4 Hz)j 2,75 (S^CHj,3H, s)} 0,91 (C-CH3,.3H, t) VII CH3 gh2c6h5 CH3SO4 7,9 až 7,2 (ar, 4H, a); 6,7 až 6,1 (Ph, 5H,5,43 (N+-CH2, 2H, s)i 3,46 (CHjSO“, 3H, s);2,69 (S-CH3, 3H, s) VIII ch3 (ch2)hch3 CH3SO4 7,9 až 7,2 (ar, 4H, a); 4,23 (B+-0H2, 2H, t)}3,49 (CH3S0" 3H, a) i 2,68 (S-CHp 3H, s); 1,8 až 0,6 (0υΗ23, 23H, a) IX C2H5 ch3 CH3SO4 7,8 až 7,2 (ar, 4H, a)i 3,79 (N*-CH3, 3H, s)j3,48 <CH3SO“, 3H, s)j 3,20 (S-CH2, 2H, q)j1,28 (C-CHp 3H, t) X CH2CH=CH2 H HS£>4 7,8 až 7,2 (ar, 4H, a); 5,9 až 5,0 (-CH^,3H, a); 3,75 (S-CH2, 2H, d) XI CH2CH=CH2 CH3 Br 7,8 až 7,2 (ar, 4H, a)j 5,8 až 5,0 (-CH-CH2,3H, a); 3,80 (S-CH2, 2H, d)j 3,78 (N+-CH3, 3H, s) XII ch2c«ch cr3 Br 7,9 až 7,2 (ar, 4H, a)} 3,95 (S-CH2, 2H, d)j3,82 (íT-Cltj, 3H, s)J 2,17 (-CH, 1H, t) XIII CHgCaCH C2H5 Br 7,9 až 7,2 (ar, 4H, a)j 4,34 (Ν+-βΗ2, 2H, q);4,00 (S-CH2, 2H, d); 2,19 (sCH, 1H, t); 1,23(c-ch3, 3H, t) XIV CH2CH(CH3)2 ch3 ch3so4 7,8 až 7,2 (ar, 4H, a); 3,78 (N+-CH3, 3H, s)j3,03 (S-CH2, 2H, d)} 1,90 (CH, 1H, n); 0,80(CH3, 6H, d) s - singlet, d - dublet, t - triplet, q - kvartet, n - nonet, a - aultiplet 239422 8
Tabulka 3
Stimule3ná a inhibičná úSinnost syntetizovaných zlúčenín podTa vynálezu číslo R r’ X" Stiaulácia mol. dm“3 Ήβη Inhibícia mol.dm“3—mni Z CH3 H HSO4 3,55 10“’3 11 CH3 ch3 CH3SO4 3,85 10“7 III CH3 ch3 C104 22,40 10“3 IV CH3 ch2ch»ch2 CH3SO4 3,60 ΙΟ’7 6,20 10“” v CH3 ch2ch=ch2 I 19,75 ,0“3 VI CH3 ch2cooc2h^ I 20,55 10“3 VII ch3 «W, CH3SO4 14,40 10“3 VIII CH3 (CH2),,CH3 CH3SO4 3,15 10“3 IX C2H5 CH3 ch3so4 5,85 io-" X ch2ch=ch2 H hso4 3,35 ΙΟ’7 XI ch2ch=ch2 ch3 Br 1,90 i°79 XII CHgCsCH ch3 Br 4,25 ,0-” XIII CHgCaCH C2«5 Br 3,45 10“’3 XIV CH2CH(CH3)2 IAA CH3 CH.S04 J 4 3,10 10“12 4,30 10-’3 2,4-D CCC 4,95 10“9 3,85 10“3 IAA - kyselina beta-indolyloctová; 2,4-D-kyselina 2,4-dichlórfenoxyoetové;CCC - 2-chlóretyltrimetylamóniumchlorid
239422 2
This invention relates to benzothiazolium salt derivatives of the formula I
wherein B is methyl, ethyl, allyl, propargyl, isobutyl, R 1 is hydrogen, methyl, ethyl, allyl, ethoxycarbonylmethyl, benzyl, dodecyl, and X "is iodine, bromine, hydrosulfate, methylsulfate, and the like; plant growth inhibitors.
A detailed literary survey was conducted in the work of 2-alkoxycarbonylmethylthio-3-alkylbenzothiazolium salt and their preparation (Sutoris V., Sekerka V., Sohler R .: AO 233 443. 2-methylthio-3-methylbenzothiazolium iodide (Fry DJ, Kendall JD: J. Chem. Soc. 1951, 1716) Moreover, the benzothiazolium salts of the invention are not yet described in the literature and no attention has been paid to their biological activity study. .
The principle of the preparation of the compounds according to the invention is that the 3-R1-2-benzothiazolinothione derivatives of formula II C = Sdi-r 1 (II) wherein r 'is the same as in formula I, react with RX where R a is X is the same as in Formula I in organic solvents such as nitromethane, acetone, tetrahydrofuran, dimethylformamide, a mixture of dimethylformamide and acetone (3: 1) or without solvent at 18-110 ° C for 30 minutes up to 24 hours.
The reaction is indicated by the following scheme: s ". C = Slil - R1
+ R x c - s -d 1 - r 1 where R, R 1 and X "are as described above: General procedures for the preparation of 2-alkylthio-3-alkylbenzothiazolium halides, hydrosulfate methylsulfates. Example 23 0.03 mole of 3-alkyl-2-benzothiazolinethone was dissolved in 15 µl of nitroaethane and after addition of 0.035 mole of the appropriate alkyl halide, the reaction was allowed to cool for 24 hours. The crystallized portion was filtered off and prenyl acetone was added. Example 2 To 0.03 aol of 3-alkyl-2-benzothiazolinone, 0.04 aol of alkyl halide was added and the mixture was heated to 70-80 ° C for 4 hours. After addition of dry acetone, the solid was isolated by filtration. EXAMPLE 3 0.03 Aol of 3-alkylbenzothlazolinothione is dissolved in 15-20 al of nitroaethane, acetone, tetrahydrofurene, diaethylforaaaid or diaethylphosphoramide and acetone (3: 1), 0.04 aol of alkyl halide is added and the reaction mixture is heated to 60 with water. up to 75 ° C for 10 hours. Example 4 Dissolve 0.03 aol of a 2-alkylthio-3-alkylbenzothiazolium halide in 50 µl of water, filter the solution and add a 5% excess of KCl 3 dissolved in 15 µl of water. From the bleached cloudiness, he drains an oil-yellow bead that crystallizes. EXAMPLE 5 4.4 g (0.035 aol) of propylene sulphate was added to 0.03 aol of 3 ' -alkyl-2-benzothiazolinetone and the reaction mixture was heated to 60-110 [deg.] C. for 1 hour to 1 hour. After cooling, acetone is added, the solid is filtered and the acetone is washed well. EXAMPLE 6 0.03 nol of 3-alkyl-2-benzothlazolinone is dissolved in 15 .mu.l of acetone and, after addition of 4.4 g (0.035 mol) of methylsulfate, the reaction mixture is heated to reflux for 2 to 3 hours. After cooling, the crystalline fraction is isolated. EXAMPLE 7 0.03 nol of 3-alkyl-2-benzothiazolynone was dissolved in 15 [mu] l of tetrahydrofuran and 3.4 g (0.035 aol) of HgSO4 were added dropwise. The precipitated crystalline fly is purified by ethanol crystals.
Analogous procedures are used to prepare alkenyl, alkynyl, ethoxycarbonylaethyl and benzyl derivatives. The results of the elemental analysis and the physical constant of the synthesized compounds of the invention are shown in Table 1. 1 H-NMR spectra were recorded on a Tesla BS 487 A pr180 IIHZ instrument in deuterated trifluoroacetic acid, internal Standard hexanethylenedlsiloxane. The results are shown in Table 2. 239422 4 The compounds of the invention are effective as mulifiers and growth inhibitors. The bastion tests and and were carried out by a modified method on a vika siata object. Example 8 illustrates the method of testing compounds of the invention for stimulatory and inhibitory activity. Priklade
Seeds of straw wolf germinated in Petri dishes in a thermostate, at a thorn of 25 ° C. Keying after 48-hour growth was exposed in molar solutions of benzothiazolium salts of general formula 1, where B, r 'and X ~ are the same. Testing was carried out in a concentration rock of 10 -16 to 10-mole. dm ~ 3, and after 24 hours of incubation, the growth of prolonged root growth was determined. In each determination, a growth effect was also performed in the control series.
As standards, beta-indolylacetic acid (IAA) and 2,4-dichlorophenoxyacetic acid (2,4-0) and 2-chloroethyltrimethylammonium chloride (CCC) were tested. The results of the stimulatory and inhibitory effect of the synthesized compounds of the invention are shown in Table 3. 5 239422 «ρ e-3
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CM CM CM CM CM 239422
Table 2
η-NMR chemical shifts (δ) of the benzothiazolium salts synthesized according to the invention No. R 1 X X I 1 CH 3 H HSO 4 7.8-7.2 (ar, 4H, a); 2.66 (S-CH3, 3H, a) IX CH3C3 CH3SO4 7.8-7.2 (ar, 4H, b) 3.78 (rf-CHp3H, s) 3.50 (CH3SO4, 3H, s) 2.70 (S-CH3, 3H, s) III OT3 CH3 C1O4 7.8-7.2 (ar, 4H, a); 3.75 (N + -CH3, 3H, s) 2.67 (S-CH3, 3H, s) IV ch3 ch2ch = ch2 CH3SO4 7.8 to 7.2 (ar, 4H, a) j 5.5 (= CH, 1H, [alpha]); 5.0 (= CH2, 2H, b); 4.86 (N * -CH 2, 2H, d); 2.71 (S-CH 3, 3H, s) in CH 3 ch 2 ch = ch 2 J 7.9-7.2 (ar, 4H, a) j 5.6 (= CH, 1H, a) {5.1 (= 0¾, 2H, a); 4.88 (M + -CH 2, 2H, d); 2.73 (S-CH 3, 3H, s); 4.00 (O-CH 2, 2H, q, J = 7.4 Hz); 2.75 (S, CH 3, 3H, s); 0.91 (C-CH 3, 4H, s); 3H, t) VII CH3 gh2c6h5 CH3SO4 7.9-7.2 (ar, 4H, a); 6.7 to 6.1 (Ph, 5H, 5.43 (N + -CH 2, 2H, s); 3.46 (CH 3 SO 2, 3H, s); 2.69 (S-CH 3, 3H, s) VIII CH3 (ch2) hch3 CH3SO4 7.9-7.2 (ar, 4H, a); 4.23 (B + -0H2, 2H, t)} 3.49 (CH3SO3H, a) 2.68 (S 1.8 to 0.6 (0υΗ23, 23H, a) IX C2H5 ch3 CH3SO4 7.8-7.2 (ar, 4H, a) 3.79 (N * -CH3, 3H); , s) 3,48 <CH 3 SO ”, 3H, s) j 3.20 (S-CH 2, 2H, q) j 1.28 (C-CHp 3H, t) X CH 2 CH = CH 2 H HS £> 4 7.8 up to 7.2 (ar, 4H, a); 5.9 to 5.0 (-CH3, 3H, a); 3.75 (S-CH2, 2H, d) XI CH2CH = CH2 CH3 Br 7.8 up to 7.2 (ar, 4H, a); 5.8 to 5.0 (-CH-CH2, 3H, a); 3.80 (S-CH2, 2H, d); 3.78 (N + -CH3 , 3H, s) XII, CH 2 Cl 3 Br 7.9-7.2 (ar, 4H, a) 3.95 (S-CH 2, 2H, d) 3.82 (t-Clt, 3H, s) J 2.17 (-CH, 1H, t) XIII CH3CaCH2H5 Br 7.9-7.2 (ar, 4H, a) j 4.34 (Ν + -βΗ2, 2H, q); 4.00 (S -CH 2, 2H, d); 2.19 (sCH, 1H, t); 1.23 (c-ch 3, 3H, t) XIV CH 2 CH (CH 3) 2 ch 3 CH 3 O 4 7.8-7.2 (ar, 4H 3.78 (N + -CH 3, 3H, s) 3.03 (S-CH 2, 2H, d) 1.90 (CH, 1H, n) 0.80 (CH 3, 6H, d) s - singlet, d - doublet, t - triplet, q - quartet, n - nonet, a - ault iplet 239422 8
Table 3
Stimulating and inhibitory activity of the synthesized compounds of the present invention No. R r 'X "Molecular Dilution" 3 ηβη Mol.dm Inhibition 3 - mni Z CH 3 H HSO 4 3.55 10 "3 11 CH3 ch3 CH3SO4 3.85 10" 7 CH3 ch3 C104 22,40 10 “3 IV CH3 ch2ch» ch2 CH3SO4 3.60 ΙΟ7 7,20 10 “” in CH3 ch2ch = ch2 I 19,75, 0 “3 VI CH3 ch2cooc2h ^ I 20,55 10 "3 VII ch3« W, CH3SO4 14.40 10 "3 VIII CH3 (CH2) ,, CH3 CH3SO4 3.15 10 '3 IX C2H5 CH3 ch3so4 5.85 io-" X ch2ch = ch2 H hso4 3.35 ΙΟ " 7 XI ch2ch = ch2 ch3 Br 1.90 i ° 79 XII CHgCsCH ch3 Br 4.25, 0- ”XIII CHgCaCH C2« 5 Br 3.45 10 ”'3 XIV CH 2 CH (CH 3) 2 IAA CH 3 CH.S04 J 4 3,10 10 “12 4,30 10-'3 2,4-D CCC 4,95 10“ 9 3,85 10 “3 IAA - beta-indolylacetic acid; 2,4-D-2,4-Dichlorophenoxy-acetic acid; CCC-2-Chloroethyltrimethylammonium chloride
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS842570A CS239422B1 (en) | 1984-04-03 | 1984-04-03 | Substituted benzothiazolium salts and a process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS842570A CS239422B1 (en) | 1984-04-03 | 1984-04-03 | Substituted benzothiazolium salts and a process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS257084A1 CS257084A1 (en) | 1985-06-13 |
| CS239422B1 true CS239422B1 (en) | 1986-01-16 |
Family
ID=5363194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS842570A CS239422B1 (en) | 1984-04-03 | 1984-04-03 | Substituted benzothiazolium salts and a process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS239422B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107580592A (en) * | 2015-05-12 | 2018-01-12 | 巴斯夫欧洲公司 | Sulfide compound as nitrification inhibitor |
-
1984
- 1984-04-03 CS CS842570A patent/CS239422B1/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107580592A (en) * | 2015-05-12 | 2018-01-12 | 巴斯夫欧洲公司 | Sulfide compound as nitrification inhibitor |
| US11053175B2 (en) | 2015-05-12 | 2021-07-06 | Basf Se | Thioether compounds as nitrification inhibitors |
| CN107580592B (en) * | 2015-05-12 | 2022-03-04 | 巴斯夫欧洲公司 | Thioether compounds as nitrification inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| CS257084A1 (en) | 1985-06-13 |
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