IL47156A - Phosphonic acid and thionophosphonic acid ester amides their preparation and their use as plantgrowth regulators - Google Patents

Phosphonic acid and thionophosphonic acid ester amides their preparation and their use as plantgrowth regulators

Info

Publication number: IL47156A
Authority: IL; Israel
Prior art keywords: compound; isopropyl; formula; iso; phosphonic acid
Prior art date: 1974-04-27

Application number

IL47156A

Other languages

English (en)

Other versions

IL47156A0 (en

Original Assignee

Bayer Ag

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.)

1974-04-27

Filing date

1975-04-24

Publication date

1977-08-31

1974-04-27 Priority claimed from DE2420627A external-priority patent/DE2420627C2/de

1975-04-24 Application filed by Bayer Ag filed Critical Bayer Ag

1975-06-25 Publication of IL47156A0 publication Critical patent/IL47156A0/xx

1977-08-31 Publication of IL47156A publication Critical patent/IL47156A/en

Links

-1 ester amides Chemical class 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 16
239000002253 acid Substances 0.000 title claims description 12
239000005648 plant growth regulator Substances 0.000 title description 4
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 88
150000001408 amides Chemical class 0.000 claims description 42
238000000034 method Methods 0.000 claims description 32
230000008569 process Effects 0.000 claims description 22
230000012010 growth Effects 0.000 claims description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
239000003085 diluting agent Substances 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
239000005864 Sulphur Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
230000008635 plant growth Effects 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
230000001105 regulatory effect Effects 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
239000011575 calcium Substances 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
229910004856 P—O—P Inorganic materials 0.000 claims 1
LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 claims 1
241000196324 Embryophyta Species 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
235000013399 edible fruits Nutrition 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
230000005070 ripening Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
230000009105 vegetative growth Effects 0.000 description 5
YMDQMMGRBWZOET-UHFFFAOYSA-N Cl.CC(C)NP(O)(=O)CCCl Chemical compound Cl.CC(C)NP(O)(=O)CCCl YMDQMMGRBWZOET-UHFFFAOYSA-N 0.000 description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241000234295 Musa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
240000003768 Solanum lycopersicum Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
230000009471 action Effects 0.000 description 3
235000021015 bananas Nutrition 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000003630 growth substance Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
239000004606 Fillers/Extenders Substances 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000001133 acceleration Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000005520 cutting process Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000010410 dusting Methods 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
150000002440 hydroxy compounds Chemical class 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
OGOPMOUFAUXUHE-UHFFFAOYSA-N 2-chloroethyl-n-ethylphosphonamidic acid Chemical compound CCNP(O)(=O)CCCl OGOPMOUFAUXUHE-UHFFFAOYSA-N 0.000 description 1
NHHZWJPOTNLLPG-UHFFFAOYSA-N 2-chloroethyl-n-propan-2-ylphosphonamidic acid Chemical compound CC(C)NP(O)(=O)CCCl NHHZWJPOTNLLPG-UHFFFAOYSA-N 0.000 description 1
RFAYOOFMTUPEFD-UHFFFAOYSA-N 2-chloroethyl-n-propylphosphonamidic acid Chemical compound CCCNP(O)(=O)CCCl RFAYOOFMTUPEFD-UHFFFAOYSA-N 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
108010088751 Albumins Proteins 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000035613 defoliation Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000003966 growth inhibitor Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
230000002015 leaf growth Effects 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000005068 transpiration Effects 0.000 description 1
239000002699 waste material Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

IL47156A 1974-04-27 1975-04-24 Phosphonic acid and thionophosphonic acid ester amides their preparation and their use as plantgrowth regulators IL47156A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2420627A DE2420627C2 (de)	1974-04-27	1974-04-27	N-iso-Propyl-2-chloräthan-(thiono)-phosphonsäureesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenwachstumsregulatoren

Publications (2)

Publication Number	Publication Date
IL47156A0 IL47156A0 (en)	1975-06-25
IL47156A true IL47156A (en)	1977-08-31

Family

ID=5914212

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL47156A IL47156A (en)	1974-04-27	1975-04-24	Phosphonic acid and thionophosphonic acid ester amides their preparation and their use as plantgrowth regulators

Country Status (5)

Country	Link
AU (1)	AU8051675A (tr)
ES (1)	ES436995A1 (tr)
IL (1)	IL47156A (tr)
IT (1)	IT1037647B (tr)
TR (1)	TR18352A (tr)

1975
- 1975-04-24 AU AU80516/75A patent/AU8051675A/en not_active Expired
- 1975-04-24 IL IL47156A patent/IL47156A/en unknown
- 1975-04-24 IT IT2275575A patent/IT1037647B/it active
- 1975-04-25 ES ES436995A patent/ES436995A1/es not_active Expired
- 1975-04-25 TR TR1835275A patent/TR18352A/tr unknown

Also Published As

Publication number	Publication date
IL47156A0 (en)	1975-06-25
ES436995A1 (es)	1977-01-16
AU8051675A (en)	1976-10-28
IT1037647B (it)	1979-11-20
TR18352A (tr)	1977-01-12

Publication	Publication Date	Title
US4315765A (en)	1982-02-16	Trialkylsulfonium salts of n-phosphonomethylglycine and their use as plant growth regulators and herbicides
EP0054382B1 (en)	1985-04-24	Triethylsulfonium salts of n-phosphonomethylglycine, production thereof, their use as plant growth regulators, herbicides and compositions containing them
US4227918A (en)	1980-10-14	Novel halogenoethyl sulphones and their use as plant growth regulators
US3885951A (en)	1975-05-27	Plant growth regulant compositions containing 2-haloethanesulphinic acid compounds
US3989525A (en)	1976-11-02	H-isopropyl-2-chloroethane-(thiono)-phosphonic acid ester amide compounds and herbicidal compositions
KR910000725B1 (ko)	1991-01-31	아세트산의 인 함유 작용성 유도체의 제조방법
US3825635A (en)	1974-07-23	2-chloroethane-(thiono)-phosphonic acid amido esters
CA1078841A (en)	1980-06-03	1,2,3-thiadiazol-5-yl-ureas useful in retarding the growth of and defoliating plants
CA1134854A (en)	1982-11-02	Amine salts of substituted n-phosphonomethylureas and their use as plant growth regulators
US3901679A (en)	1975-08-26	2-chloroethane-phosphonic-(or thiono phosphonic) acid amido compounds as plant growth regulants
US4292072A (en)	1981-09-29	Novel α-isocyanocarboxylic acid compounds and plant growth regulant compositions
EP0046069A1 (en)	1982-02-17	Herbicidal and plant growth regulant diphenylpyridazinones
US4376644A (en)	1983-03-15	Tri-mixed alkylsulfonium salts of N-phosphonomethylglycine and their use as plant growth regulators and herbicides
US3920727A (en)	1975-11-18	Novel n-arylcarbamic acid esters
IL47156A (en)	1977-08-31	Phosphonic acid and thionophosphonic acid ester amides their preparation and their use as plantgrowth regulators
US4239528A (en)	1980-12-16	Plant growth regulating compositions and methods using alpha-isocyanocarboxylic acid compounds
US4065288A (en)	1977-12-27	Novel 2-chloroethane-(thiono)-phosphonic acid amido compounds and plant growth inhibiting compositions
US4104049A (en)	1978-08-01	Chlorine-substituted vinylaminobenzoic acid compounds and plant growth regulant compositions
US3972705A (en)	1976-08-03	Amidothionophosphonic acid ester containing plant growth regulants
US4076517A (en)	1978-02-28	Method of inhibiting the growth of plants with phospholenium salts
US3979204A (en)	1976-09-07	Plant growth regulant compositions comprising 2-cyano-bicyclo[2,2,1]heptane
US4350520A (en)	1982-09-21	Plant growth regulant compositions
US4067721A (en)	1978-01-10	Imidazolidinedione compounds and plant growth influencing compositions
EP0007162B1 (en)	1982-07-14	Novel n-substituted 2-oxo-3-benzothiazoline derivatives, their use as leguminous plant growth regulants, and plant growth regulating compositions containing said derivatives as the active ingredients
US4482737A (en)	1984-11-13	Preparation of N-substituted N-isocyanatocarbonyl-carbamates