CS259882B2 - 2-chloro-ethyl phosphonic acid esters and plant growth regulating agents containing same as active ingredient. - Google Patents

2-chloro-ethyl phosphonic acid esters and plant growth regulating agents containing same as active ingredient. Download PDF

Info

Publication number: CS259882B2
Authority: CS; Czechoslovakia
Prior art keywords: dihydro; yloxy; acid; plant growth; diethyl ester
Prior art date: 1984-07-18

Application number

CS855348A

Other languages

Czech (cs)

English (en)

Other versions

CS534885A2 (en

Inventor

Sandor Balint

Judit Bencsik

Ferenc Fodor

Andras Horvath

Elemer Tomordi

Csaba Soptei

Jozsef Karsai

Endre Sebestyen

Sandor Gaal

Ivan Gardi

Gyorgy Kis

Andras Papp

Original Assignee

Nitrokemia Ipartelepek

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-07-18

Filing date

1985-07-18

Publication date

1988-11-15

1985-07-18 Application filed by Nitrokemia Ipartelepek filed Critical Nitrokemia Ipartelepek

1988-03-15 Publication of CS534885A2 publication Critical patent/CS534885A2/cs

1988-11-15 Publication of CS259882B2 publication Critical patent/CS259882B2/cs

Links

230000008635 plant growth Effects 0.000 title claims abstract description 21
239000004480 active ingredient Substances 0.000 title abstract description 11
230000001105 regulatory effect Effects 0.000 title abstract description 7
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical class OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 title description 21
239000003795 chemical substances by application Substances 0.000 title description 3
-1 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl Chemical group 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
150000001768 cations Chemical class 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
238000002360 preparation method Methods 0.000 claims description 18
HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 5
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 5
230000008569 process Effects 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 46
239000005648 plant growth regulator Substances 0.000 abstract description 3
125000006526 (C1-C2) alkyl group Chemical group 0.000 abstract 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
238000011282 treatment Methods 0.000 description 43
241000196324 Embryophyta Species 0.000 description 23
230000012010 growth Effects 0.000 description 21
238000012360 testing method Methods 0.000 description 19
235000007688 Lycopersicon esculentum Nutrition 0.000 description 17
240000003768 Solanum lycopersicum Species 0.000 description 17
230000000694 effects Effects 0.000 description 17
244000068988 Glycine max Species 0.000 description 16
235000010469 Glycine max Nutrition 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000003306 harvesting Methods 0.000 description 15
MSHBKNAWDRSOSF-UHFFFAOYSA-N 7-(2-diethoxyphosphorylethoxy)-2,2-dimethyl-3h-1-benzofuran Chemical compound CCOP(=O)(OCC)CCOC1=CC=CC2=C1OC(C)(C)C2 MSHBKNAWDRSOSF-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
230000008859 change Effects 0.000 description 13
239000000126 substance Substances 0.000 description 13
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 11
239000007788 liquid Substances 0.000 description 11
235000003222 Helianthus annuus Nutrition 0.000 description 10
239000002689 soil Substances 0.000 description 10
239000007921 spray Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
241000208818 Helianthus Species 0.000 description 7
239000000243 solution Substances 0.000 description 7
235000008534 Capsicum annuum var annuum Nutrition 0.000 description 6
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 description 5
235000002566 Capsicum Nutrition 0.000 description 5
239000006002 Pepper Substances 0.000 description 5
241000722363 Piper Species 0.000 description 5
235000016761 Piper aduncum Nutrition 0.000 description 5
235000017804 Piper guineense Nutrition 0.000 description 5
235000008184 Piper nigrum Nutrition 0.000 description 5
241000209140 Triticum Species 0.000 description 5
235000021307 Triticum Nutrition 0.000 description 5
240000008042 Zea mays Species 0.000 description 5
235000002017 Zea mays subsp mays Nutrition 0.000 description 5
238000005507 spraying Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000005292 vacuum distillation Methods 0.000 description 5
RWQJSKNITXLYII-UHFFFAOYSA-N 7-(2-diethoxyphosphorylethoxy)-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OCCP(=O)(OCC)OCC)=CC=C21 RWQJSKNITXLYII-UHFFFAOYSA-N 0.000 description 4
240000004160 Capsicum annuum Species 0.000 description 4
235000007862 Capsicum baccatum Nutrition 0.000 description 4
239000001728 capsicum frutescens Substances 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
230000004720 fertilization Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 3
JSTAJDYYTGMGEN-UHFFFAOYSA-N 2-(4-methyl-2-oxochromen-7-yl)oxyethylphosphonic acid Chemical compound CC1=CC(OC2=CC(=CC=C12)OCCP(O)(O)=O)=O JSTAJDYYTGMGEN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
244000020551 Helianthus annuus Species 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
235000009973 maize Nutrition 0.000 description 3
238000003359 percent control normalization Methods 0.000 description 3
239000003444 phase transfer catalyst Substances 0.000 description 3
239000001103 potassium chloride Substances 0.000 description 3
235000011164 potassium chloride Nutrition 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002426 superphosphate Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 description 2
IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
UBXUESSWMYFYAL-UHFFFAOYSA-N 7-(2-bromoethoxy)-2,2,4-trimethylchromene Chemical compound BrCCOC1=CC=C2C(C)=CC(C)(C)OC2=C1 UBXUESSWMYFYAL-UHFFFAOYSA-N 0.000 description 2
XLLJFWFFIDCGMI-UHFFFAOYSA-N 7-(2-bromoethoxy)-4-methylchromen-2-one Chemical compound C1=C(OCCBr)C=CC2=C1OC(=O)C=C2C XLLJFWFFIDCGMI-UHFFFAOYSA-N 0.000 description 2
ZMBGUZNIPBCBMC-UHFFFAOYSA-N 7-(2-chloroethoxy)-2,2-dimethyl-3h-1-benzofuran Chemical compound C1=CC(OCCCl)=C2OC(C)(C)CC2=C1 ZMBGUZNIPBCBMC-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
240000008384 Capsicum annuum var. annuum Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
238000004821 distillation Methods 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
UWTUEMKLYAGTNQ-UHFFFAOYSA-N 1,2-dibromoethene Chemical group BrC=CBr UWTUEMKLYAGTNQ-UHFFFAOYSA-N 0.000 description 1
JJOHSFWZFCGFNT-UHFFFAOYSA-N 1-(4-bromo-3-chlorophenyl)-3-methoxy-1-methylurea Chemical compound CONC(=O)N(C)C1=CC=C(Br)C(Cl)=C1 JJOHSFWZFCGFNT-UHFFFAOYSA-N 0.000 description 1
OLKWMFUGWXLVNM-UHFFFAOYSA-N 2,2,4-trimethylchromen-7-ol Chemical compound OC1=CC=C2C(C)=CC(C)(C)OC2=C1 OLKWMFUGWXLVNM-UHFFFAOYSA-N 0.000 description 1
GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
BOEGWRHPJUASPQ-UHFFFAOYSA-N 2-chloroethyl(ethoxy)phosphinic acid Chemical compound CCOP(O)(=O)CCCl BOEGWRHPJUASPQ-UHFFFAOYSA-N 0.000 description 1
JOJBIXXQYQURIR-UHFFFAOYSA-N 2-methoxyethylphosphonic acid Chemical compound COCCP(O)(O)=O JOJBIXXQYQURIR-UHFFFAOYSA-N 0.000 description 1
XPIQJMUYUKAKNX-VOTSOKGWSA-N 3-[(2e)-octa-2,7-dienyl]oxolane-2,5-dione Chemical class C=CCCC\C=C\CC1CC(=O)OC1=O XPIQJMUYUKAKNX-VOTSOKGWSA-N 0.000 description 1
CSBLCDBHJJXRBX-UHFFFAOYSA-N 7-[2-[bis(2-chloroethoxy)phosphoryl]ethoxy]-2,2-dimethyl-3h-1-benzofuran Chemical compound C1=CC(OCCP(=O)(OCCCl)OCCCl)=C2OC(C)(C)CC2=C1 CSBLCDBHJJXRBX-UHFFFAOYSA-N 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
229930192334 Auxin Natural products 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
GHMDBLDLEYKYOS-UHFFFAOYSA-N CC1(CC2=C(O1)C(=CC=C2)OCCP(=O)(OCCOC)OCCOC)C Chemical compound CC1(CC2=C(O1)C(=CC=C2)OCCP(=O)(OCCOC)OCCOC)C GHMDBLDLEYKYOS-UHFFFAOYSA-N 0.000 description 1
235000008536 Capsicum baccatum var pendulum Nutrition 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
240000004713 Pisum sativum Species 0.000 description 1
235000010582 Pisum sativum Nutrition 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
230000010757 Reduction Activity Effects 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000002363 auxin Substances 0.000 description 1
AQKNQRMIGNOQQF-UHFFFAOYSA-N azane;2-(2,4-dichlorophenoxy)acetic acid Chemical compound [NH4+].[O-]C(=O)COC1=CC=C(Cl)C=C1Cl AQKNQRMIGNOQQF-UHFFFAOYSA-N 0.000 description 1
VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229960000956 coumarin Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
230000017363 positive regulation of growth Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000026267 regulation of growth Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000010408 sweeping Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS855348A 1984-07-18 1985-07-18 2-chloro-ethyl phosphonic acid esters and plant growth regulating agents containing same as active ingredient. CS259882B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU842801A HU190580B (en)	1984-07-18	1984-07-18	Plant growth regulating compositions comprising phosphonic acid-esters as active substance

Publications (2)

Publication Number	Publication Date
CS534885A2 CS534885A2 (en)	1988-03-15
CS259882B2 true CS259882B2 (en)	1988-11-15

Family

ID=10961160

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS855348A CS259882B2 (en)	1984-07-18	1985-07-18	2-chloro-ethyl phosphonic acid esters and plant growth regulating agents containing same as active ingredient.

Country Status (10)

Country	Link
US (1)	US4776874A (de)
EP (1)	EP0187806A1 (de)
JP (1)	JPS61502754A (de)
BG (1)	BG47499A3 (de)
CS (1)	CS259882B2 (de)
DD (1)	DD238910A5 (de)
DK (1)	DK123986D0 (de)
ES (1)	ES8706708A1 (de)
HU (1)	HU190580B (de)
WO (1)	WO1986000903A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PE20141468A1 (es)	2010-12-21	2014-11-05	Bayer Cropscience Lp	Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas
MX2014002890A (es)	2011-09-12	2015-01-19	Bayer Cropscience Lp	Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos.

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3531549A (en) *	1967-02-23	1970-09-29	Gaf Corp	Catechol half esters of beta-haloethylphosphonic acid
US3551528A (en) *	1967-02-23	1970-12-29	Gaf Corp	Phosphonic acid esters and the methol for their preparation
US4042370A (en) *	1974-09-18	1977-08-16	Sandoz Ltd.	Di-(acyloxyalkyl)-β-haloethane-phosphonates and dithiophosphonates and use as plant growth regulators
US4172863A (en) *	1976-06-14	1979-10-30	Waldmann John J	Halogen-containing phosphates
CA1085870A (en) *	1976-12-20	1980-09-16	Robert J. Kiesel	Preparation of haloalylphosphonic acid
DD132632A1 (de) *	1977-08-12	1978-10-18	Bernhard Hesse	Mittel zur beeinflussung des pflanzenwachstums
DE3001895A1 (de) *	1980-01-19	1981-07-23	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von alkanphosphonsaeurediarylester und alkanphosphinsaeurearylestern
IL71373A (en) *	1983-04-07	1987-07-31	Mitsubishi Chem Ind	O-(2,3-dihydro-2,2-dimethyl-7 benzofuranyl)thiophosphoric and phosphonic esters,process for their production and pesticidal compositions containing them
HU190579B (en) *	1984-07-18	1986-09-29	Nitrokemia Ipartelepek,Hu	Plant growth regulating compositions comprising etherified hydroxy-alkyl-phosphonic acid-derivatives as active substance

1984
- 1984-07-18 HU HU842801A patent/HU190580B/hu not_active IP Right Cessation
1985
- 1985-07-12 JP JP60503199A patent/JPS61502754A/ja active Pending
- 1985-07-12 EP EP85903354A patent/EP0187806A1/de not_active Ceased
- 1985-07-12 WO PCT/HU1985/000043 patent/WO1986000903A1/en not_active Ceased
- 1985-07-15 DD DD85278589A patent/DD238910A5/de unknown
- 1985-07-17 US US06/839,498 patent/US4776874A/en not_active Expired - Fee Related
- 1985-07-18 CS CS855348A patent/CS259882B2/cs unknown
- 1985-07-18 ES ES545632A patent/ES8706708A1/es not_active Expired
1986
- 1986-03-18 BG BG074116A patent/BG47499A3/xx unknown
- 1986-03-18 DK DK123986A patent/DK123986D0/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
HU190580B (en)	1986-09-29
JPS61502754A (ja)	1986-11-27
US4776874A (en)	1988-10-11
DK123986A (da)	1986-03-18
EP0187806A1 (de)	1986-07-23
ES545632A0 (es)	1987-07-01
WO1986000903A1 (en)	1986-02-13
BG47499A3 (en)	1990-07-16
DK123986D0 (da)	1986-03-18
CS534885A2 (en)	1988-03-15
DD238910A5 (de)	1986-09-10
ES8706708A1 (es)	1987-07-01

Publication	Publication Date	Title
SU803845A3 (ru)	1981-02-07	Гербицидный состав
NO130107B (de)	1974-07-08
HU194029B (en)	1988-01-28	Herbicidal and plant growth regulator composition comprising aluminium-n-(phosponomethyl)-glycine as active substance and process for preparing the active substance
SU648046A3 (ru)	1979-02-15	Гербицидное средство
US3985773A (en)	1976-10-12	Plant growth regulators
JPS6150922B2 (de)	1986-11-06
SU1486049A3 (ru)	1989-06-07	Способ регулирования роста сельскохозяйственных культур
CS259882B2 (en)	1988-11-15	2-chloro-ethyl phosphonic acid esters and plant growth regulating agents containing same as active ingredient.
HU182985B (en)	1984-03-28	Fungicide and bactericide compositions and process for producing new isothiouromium-phosphite derivatives as active agents
HU182905B (en)	1984-03-28	Compositions for the plant growth regulation containing substituted benzazolyl-thio-alkancarboxylic acid derivatives
US3997595A (en)	1976-12-14	2-Chloroethanephosphonic acid derivatives
US3681406A (en)	1972-08-01	N-alkoxyalkylidenesulfonamide compounds
SU843696A3 (ru)	1981-06-30	Гербицидный состав
US3832155A (en)	1974-08-27	N-alkoxyalkylidenesulfonamide compounds as herbicides
SU833141A3 (ru)	1981-05-23	Способ регулировани роста растений сои
JPS5915881B2 (ja)	1984-04-12	ジブロモ置換プロピオンアミド類、除草剤解毒用組成物およびそれを含む除草用組成物
CS208675B2 (en)	1981-09-15	Herbicide means and means for regulation of the pod stuff and method of maikng the active agent
RU2060988C1 (ru)	1996-05-27	Замещенное производное бициклогептандиона и гербицидная композиция
EP0276204A2 (de)	1988-07-27	Pyridingametozide
JPH07522B2 (ja)	1995-01-11	植物生長調整剤
GB1593541A (en)	1981-07-15	Carbamate esters of hydroxyaryl sulphonium salts and methods of regulating plant growth employing them
JPH0326200B2 (de)	1991-04-10
KR810000852B1 (ko)	1981-08-10	신규 안식향산 아닐리드 유도체의 제조방법
JPS623801B2 (de)	1987-01-27
JPS62167710A (ja)	1987-07-24	稲の健苗育成剤