IL101539A - Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing - Google Patents

Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing

Info

Publication number: IL101539A
Authority: IL; Israel
Prior art keywords: salt; formula; glycine; phosphonomethyl; ammonium
Prior art date: 1991-04-16

Application number

IL10153992A

Other languages

English (en)

Hebrew (he)

Other versions

IL101539A0 (en

Original Assignee

Monsanto Europe Sa

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.)

1991-04-16

Filing date

1992-04-09

Publication date

1998-09-24

1991-04-16 Priority claimed from HU911248A external-priority patent/HU214947B/hu

1991-07-19 Priority claimed from HU912427A external-priority patent/HU212802B/hu

1991-12-27 Priority claimed from HU914115A external-priority patent/HU214941B/hu

1992-04-09 Application filed by Monsanto Europe Sa filed Critical Monsanto Europe Sa

1992-12-30 Publication of IL101539A0 publication Critical patent/IL101539A0/xx

1998-09-24 Publication of IL101539A publication Critical patent/IL101539A/en

Links

XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical class OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims description 103
238000002360 preparation method Methods 0.000 title claims description 12
230000000361 pesticidal effect Effects 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 82
239000007787 solid Substances 0.000 claims abstract description 39
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 14
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 97
239000000047 product Substances 0.000 claims description 81
238000000034 method Methods 0.000 claims description 61
239000000203 mixture Substances 0.000 claims description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
239000002253 acid Substances 0.000 claims description 37
238000002844 melting Methods 0.000 claims description 29
230000008018 melting Effects 0.000 claims description 29
239000013078 crystal Substances 0.000 claims description 25
-1 aromatic alcohols Chemical class 0.000 claims description 23
150000001412 amines Chemical class 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
239000004480 active ingredient Substances 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 17
DIZXPRVREZXWFY-UHFFFAOYSA-N O[PH2]=O.CCCC(N)C(O)=O Chemical compound O[PH2]=O.CCCC(N)C(O)=O DIZXPRVREZXWFY-UHFFFAOYSA-N 0.000 claims description 13
239000000575 pesticide Substances 0.000 claims description 12
239000000243 solution Substances 0.000 claims description 12
238000010521 absorption reaction Methods 0.000 claims description 11
239000000376 reactant Substances 0.000 claims description 11
238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 10
230000002363 herbicidal effect Effects 0.000 claims description 9
239000002798 polar solvent Substances 0.000 claims description 9
238000002441 X-ray diffraction Methods 0.000 claims description 8
239000000654 additive Substances 0.000 claims description 8
150000003863 ammonium salts Chemical class 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
150000002500 ions Chemical class 0.000 claims description 7
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
239000011877 solvent mixture Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000725 suspension Substances 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
238000001914 filtration Methods 0.000 claims description 4
ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
230000008635 plant growth Effects 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
PDYXIVPKOMYDOK-UHFFFAOYSA-N Glyphosate-monoammonium Chemical compound [NH4+].OC(=O)CNCP(O)([O-])=O PDYXIVPKOMYDOK-UHFFFAOYSA-N 0.000 claims description 3
IQELFXQZJVWTKC-UHFFFAOYSA-N [O-][PH2]=O.CC(C)[NH3+].CC(C)[NH3+].CCCC(N)C([O-])=O Chemical compound [O-][PH2]=O.CC(C)[NH3+].CC(C)[NH3+].CCCC(N)C([O-])=O IQELFXQZJVWTKC-UHFFFAOYSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
238000011109 contamination Methods 0.000 claims description 3
239000006185 dispersion Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
229920003169 water-soluble polymer Polymers 0.000 claims description 3
239000006227 byproduct Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
150000005846 sugar alcohols Polymers 0.000 claims description 2
229920002554 vinyl polymer Polymers 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims 1
230000008030 elimination Effects 0.000 claims 1
238000003379 elimination reaction Methods 0.000 claims 1
125000005208 trialkylammonium group Chemical group 0.000 claims 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 abstract description 2
125000003282 alkyl amino group Chemical group 0.000 abstract 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000005562 Glyphosate Substances 0.000 description 20
229940097068 glyphosate Drugs 0.000 description 20
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 17
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 16
229910052921 ammonium sulfate Inorganic materials 0.000 description 16
235000011130 ammonium sulphate Nutrition 0.000 description 16
239000004471 Glycine Substances 0.000 description 15
239000001166 ammonium sulphate Substances 0.000 description 14
150000002191 fatty alcohols Chemical class 0.000 description 13
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 13
150000003973 alkyl amines Chemical class 0.000 description 12
239000000194 fatty acid Substances 0.000 description 10
239000000463 material Substances 0.000 description 10
239000002002 slurry Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
235000014113 dietary fatty acids Nutrition 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
229930195729 fatty acid Natural products 0.000 description 8
238000012360 testing method Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000005561 Glufosinate Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
239000004202 carbamide Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
KRICRZPJPJLRSU-UHFFFAOYSA-N [NH4+].[NH4+].[O-][PH2]=O.CCCC(N)C([O-])=O Chemical compound [NH4+].[NH4+].[O-][PH2]=O.CCCC(N)C([O-])=O KRICRZPJPJLRSU-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
229920000847 nonoxynol Polymers 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 3
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 3
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
UEYFKZOEGBKMKP-UHFFFAOYSA-N acetic acid;propan-2-amine Chemical compound CC(C)[NH3+].CC([O-])=O UEYFKZOEGBKMKP-UHFFFAOYSA-N 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
235000012538 ammonium bicarbonate Nutrition 0.000 description 3
239000001099 ammonium carbonate Substances 0.000 description 3
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
230000001105 regulatory effect Effects 0.000 description 3
239000012265 solid product Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 2
239000005971 1-naphthylacetic acid Substances 0.000 description 2
XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 2
XNXADQRVRLZXAD-UHFFFAOYSA-N 2-(2-phosphonoethylamino)acetic acid Chemical compound OC(=O)CNCCP(O)(O)=O XNXADQRVRLZXAD-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical group CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 2
NAXKFVIRJICPAO-LHNWDKRHSA-N [(1R,3S,4R,6R,7R,9S,10S,12R,13S,15S,16R,18S,19S,21S,22S,24S,25S,27S,28R,30R,31R,33S,34S,36R,37R,39R,40S,42R,44R,46S,48S,50R,52S,54S,56S)-46,48,50,52,54,56-hexakis(hydroxymethyl)-2,8,14,20,26,32,38,43,45,47,49,51,53,55-tetradecaoxa-5,11,17,23,29,35,41-heptathiapentadecacyclo[37.3.2.23,7.29,13.215,19.221,25.227,31.233,37.04,6.010,12.016,18.022,24.028,30.034,36.040,42]hexapentacontan-44-yl]methanol Chemical compound OC[C@H]1O[C@H]2O[C@H]3[C@H](CO)O[C@H](O[C@H]4[C@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@H]6[C@H](CO)O[C@H](O[C@H]7[C@H](CO)O[C@@H](O[C@H]8[C@H](CO)O[C@@H](O[C@@H]1[C@@H]1S[C@@H]21)[C@@H]1S[C@H]81)[C@H]1S[C@@H]71)[C@H]1S[C@H]61)[C@H]1S[C@@H]51)[C@H]1S[C@@H]41)[C@H]1S[C@H]31 NAXKFVIRJICPAO-LHNWDKRHSA-N 0.000 description 2
229960001413 acetanilide Drugs 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000005210 alkyl ammonium group Chemical group 0.000 description 2
229940077464 ammonium ion Drugs 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
229960004217 benzyl alcohol Drugs 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
238000000227 grinding Methods 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical class CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 2
230000010355 oscillation Effects 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000010773 plant oil Substances 0.000 description 2
229960004063 propylene glycol Drugs 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical class CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 description 1
239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
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 1
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
PAXFBVJVHLLRNY-UHFFFAOYSA-N 2-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]-4-ethyl-3-sulfamoylbenzoic acid Chemical group CCC1=C(C(=C(C=C1)C(=O)O)C(=O)NC2=NC(=CC(=N2)Cl)OC)S(=O)(=O)N PAXFBVJVHLLRNY-UHFFFAOYSA-N 0.000 description 1
SNDPXSYFESPGGJ-UHFFFAOYSA-N 2-aminopentanoic acid Chemical compound CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical group FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
BRPCDOLEVHTTRE-UHFFFAOYSA-N 6-oxo-6-propan-2-yloxyhexanoic acid Chemical compound CC(C)OC(=O)CCCCC(O)=O BRPCDOLEVHTTRE-UHFFFAOYSA-N 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
101100389431 Caenorhabditis elegans enol-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
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 description 1
239000005639 Lauric acid Substances 0.000 description 1
OXPCWUWUWIWSGI-MSUUIHNZSA-N Lauryl oleate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC OXPCWUWUWIWSGI-MSUUIHNZSA-N 0.000 description 1
239000005573 Linuron Substances 0.000 description 1
239000005574 MCPA Chemical group 0.000 description 1
239000005575 MCPB Substances 0.000 description 1
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WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
241001069925 Orestes Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
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239000012190 activator Substances 0.000 description 1
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
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150000001721 carbon Chemical group 0.000 description 1
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239000008121 dextrose Substances 0.000 description 1
ISPMIQMKDKSQJY-UHFFFAOYSA-N di(propan-2-yl)azanium;2-(phosphonomethylamino)acetate Chemical compound CC(C)NC(C)C.OC(=O)CNCP(O)(O)=O ISPMIQMKDKSQJY-UHFFFAOYSA-N 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
229960002380 dibutyl phthalate Drugs 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
WBBZUMDPZLYKIZ-UHFFFAOYSA-N ethylammonium propionate Chemical compound CC[NH3+].CCC([O-])=O WBBZUMDPZLYKIZ-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
150000002332 glycine derivatives Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
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239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940074928 isopropyl myristate Drugs 0.000 description 1
XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
229940075495 isopropyl palmitate Drugs 0.000 description 1
229940089456 isopropyl stearate Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
SUUDTPGCUKBECW-UHFFFAOYSA-N n-propylformamide Chemical compound CCCNC=O SUUDTPGCUKBECW-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003090 pesticide formulation Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000000243 photosynthetic effect Effects 0.000 description 1
NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical group NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
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239000002861 polymer material Substances 0.000 description 1
229940068984 polyvinyl alcohol Drugs 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical group ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
238000006276 transfer reaction Methods 0.000 description 1
WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000003466 welding Methods 0.000 description 1
239000004563 wettable powder 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/65—Insulin-like growth factors, i.e. somatomedins, e.g. IGF-1, IGF-2
- 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
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Toxicology (AREA)
Genetics & Genomics (AREA)
Environmental Sciences (AREA)
Wood Science & Technology (AREA)
Dentistry (AREA)
Plant Pathology (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Gastroenterology & Hepatology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Biophysics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Ophthalmology & Optometry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Drying Of Gases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

IL10153992A 1991-04-16 1992-04-09 Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing IL101539A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
HU911248A HU214947B (hu)	1991-04-16	1991-04-16	Hatóanyagként nemhigroszkópos glifozát-monoammónium-sókat tartalmazó fitoaktív készítmények és eljárás azok, valamint hatóanyagaik előállítására
HU912427A HU212802B (en)	1991-07-19	1991-07-19	Phytoactive sack-like composition containing glyphosate-izopropylamine salt
HU914115A HU214941B (hu)	1991-12-27	1991-12-27	Glufozinátsót tartalmazó herbicid készítmények és eljárás a hatóanyag előállítására

Publications (2)

Publication Number	Publication Date
IL101539A0 IL101539A0 (en)	1992-12-30
IL101539A true IL101539A (en)	1998-09-24

Family

ID=27269953

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10153992A IL101539A (en)	1991-04-16	1992-04-09	Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing

Country Status (26)

Country	Link
US (3)	US5324708A (el)
EP (1)	EP0537318B1 (el)
JP (1)	JP2520218B2 (el)
KR (1)	KR960003896B1 (el)
AT (1)	ATE139236T1 (el)
AU (1)	AU653226B2 (el)
BG (1)	BG97162A (el)
BR (1)	BR9205234A (el)
CA (1)	CA2084663C (el)
CZ (1)	CZ366992A3 (el)
DE (1)	DE69211473T2 (el)
DK (1)	DK0537318T3 (el)
ES (1)	ES2089523T3 (el)
FI (1)	FI925702A0 (el)
GR (1)	GR3021027T3 (el)
IE (1)	IE921211A1 (el)
IL (1)	IL101539A (el)
MX (1)	MX9201731A (el)
NO (1)	NO300545B1 (el)
PL (1)	PL169534B1 (el)
PT (1)	PT100387A (el)
RO (1)	RO107950B1 (el)
SI (1)	SI9200053A (el)
SK (1)	SK366992A3 (el)
WO (1)	WO1992018513A1 (el)
YU (1)	YU39292A (el)

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US5580841A (en) *	1985-05-29	1996-12-03	Zeneca Limited	Solid, phytoactive compositions and method for their preparation
US5468720A (en) *	1993-07-20	1995-11-21	Basf Corporation	High concentrated, solid mepiquat chloride products and processes for making dry form solid mepiquat chloride powder and tablets
TW289726B (el) *	1993-09-17	1996-11-01	Sankyo Co
US5516747A (en) *	1994-04-18	1996-05-14	Henkel Corporation	Pesticidal surfactant mixtures comprising alkyl polyglycosides and alkyl naphthalene sulfonates
US5614468A (en) *	1995-06-07	1997-03-25	Monsanto Company	Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a liquid-solid reaction system
US5633397A (en) *	1995-06-07	1997-05-27	Monsanto Company	Preparation of ammonium glyphosate via a gas-solid reaction system
US5710103A (en) *	1996-04-03	1998-01-20	Albemarle Corporation	Glyphosate compositions comprising hydrocarbyl dimethyl amine oxide and quaternary ammonium halide
US5700760A (en) *	1996-04-03	1997-12-23	Albemarle Corporation	Herbicidal and plant growth regulant compositions and their use
US5783516A (en) *	1996-06-28	1998-07-21	Albemarle Corporation	Herbicidal and plant growth regulant compositions and their use
US5703016A (en) *	1996-09-30	1997-12-30	Albemarle Corporation	Surfactant composition for use with glyphosate comprising dimethyl amine oxide, polyethoxylated alcohol, and pyridinium halide
DE19752552A1 (de)	1997-11-27	1999-06-02	Hoechst Schering Agrevo Gmbh	Tensidsysteme für flüssige wässrige Zubereitungen
ATE277517T1 (de)	1999-07-28	2004-10-15	Monsanto Technology Llp	Verfahren zur herstellung einer nachhaltig verarbeitbaren ammonium glyphosat paste
US6448434B1 (en)	1999-07-29	2002-09-10	Monsanto Technology Llc	Process for making ammonium glyphosate powder
US6599858B1 (en)	1999-07-29	2003-07-29	Monsanto Technology Llc	Process for making ammonium glyphosate flakes
US6734142B2 (en)	2001-04-23	2004-05-11	Monsanto Technology Llc	Ammonium glyphosate compositions and process for their preparation
GB0207438D0 (en) *	2002-03-28	2002-05-08	Syngenta Ltd	Formulation
EP1538910A2 (en)	2002-08-31	2005-06-15	Monsanto Technology LLC	Process for the preparation of a dry pesticidal composition containing a dicarboxylate component
US20050037924A1 (en) *	2002-08-31	2005-02-17	Monsanto Technology Llc	Sodium glyphosate compositions and process for their preparation
US7223718B2 (en) *	2005-03-07	2007-05-29	Falcon Lab Llc	Enhanced glyphosate herbicidal concentrates
CN101395164A (zh) *	2006-01-10	2009-03-25	罗伊·J·于	N-(膦酰基烷基)-氨基酸、其衍生物和组合物以及使用方法
BRPI0702341B1 (pt) *	2007-05-16	2016-06-14	Ricardo Amaral Remer	glufosinato sólido solúvel para defensivo agrícola, processo para sua obtenção e processo de controle de pragas agrícolas
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1992
- 1992-04-09 IL IL10153992A patent/IL101539A/en not_active IP Right Cessation
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- 1992-04-15 SI SI19929200053A patent/SI9200053A/sl unknown
- 1992-04-15 DK DK92909461.3T patent/DK0537318T3/da active
- 1992-04-15 PT PT100387A patent/PT100387A/pt not_active Application Discontinuation
- 1992-04-15 ES ES92909461T patent/ES2089523T3/es not_active Expired - Lifetime
- 1992-04-15 JP JP4508681A patent/JP2520218B2/ja not_active Expired - Lifetime
- 1992-04-15 BR BR9205234A patent/BR9205234A/pt not_active Application Discontinuation
- 1992-04-15 DE DE69211473T patent/DE69211473T2/de not_active Expired - Fee Related
- 1992-04-15 AT AT92909461T patent/ATE139236T1/de not_active IP Right Cessation
- 1992-04-15 RO RO92-01557A patent/RO107950B1/ro unknown
- 1992-04-15 EP EP92909461A patent/EP0537318B1/en not_active Expired - Lifetime
- 1992-04-15 CA CA002084663A patent/CA2084663C/en not_active Expired - Fee Related
- 1992-04-15 YU YU39292A patent/YU39292A/sh unknown
- 1992-04-15 IE IE121192A patent/IE921211A1/en not_active Application Discontinuation
- 1992-04-15 PL PL92297358A patent/PL169534B1/pl unknown
- 1992-04-15 KR KR1019920703204A patent/KR960003896B1/ko not_active IP Right Cessation
- 1992-04-15 AU AU16535/92A patent/AU653226B2/en not_active Ceased
- 1992-04-15 WO PCT/HU1992/000016 patent/WO1992018513A1/en not_active Application Discontinuation
- 1992-04-16 US US07/869,925 patent/US5324708A/en not_active Expired - Fee Related
- 1992-12-11 BG BG97162A patent/BG97162A/xx unknown
- 1992-12-15 NO NO924856A patent/NO300545B1/no unknown
- 1992-12-15 FI FI925702A patent/FI925702A0/fi unknown
- 1992-12-15 SK SK3669-92A patent/SK366992A3/sk unknown
- 1992-12-15 CZ CS923669A patent/CZ366992A3/cs unknown
1994
- 1994-02-04 US US08/192,414 patent/US5410075A/en not_active Expired - Fee Related
1995
- 1995-04-14 US US08/422,265 patent/US5543562A/en not_active Expired - Fee Related
1996
- 1996-09-12 GR GR960402380T patent/GR3021027T3/el unknown

Also Published As

Publication number	Publication date
US5543562A (en)	1996-08-06
EP0537318A1 (en)	1993-04-21
SK366992A3 (en)	1995-05-10
NO924856L (no)	1992-12-15
CA2084663A1 (en)	1992-10-17
SI9200053A (en)	1992-11-27
KR930701459A (ko)	1993-06-11
FI925702A (fi)	1992-12-15
CA2084663C (en)	1997-12-23
CZ366992A3 (en)	1993-05-12
AU653226B2 (en)	1994-09-22
US5410075A (en)	1995-04-25
RO107950B1 (ro)	1994-01-31
PT100387A (pt)	1993-07-30
US5324708A (en)	1994-06-28
BG97162A (en)	1994-06-30
YU39292A (sh)	1994-06-24
NO924856D0 (no)	1992-12-15
DE69211473D1 (de)	1996-07-18
ES2089523T3 (es)	1996-10-01
ATE139236T1 (de)	1996-06-15
JP2520218B2 (ja)	1996-07-31
DE69211473T2 (de)	1997-01-09
IL101539A0 (en)	1992-12-30
EP0537318B1 (en)	1996-06-12
PL169534B1 (pl)	1996-07-31
WO1992018513A1 (en)	1992-10-29
MX9201731A (es)	1994-06-30
KR960003896B1 (ko)	1996-03-23
GR3021027T3 (en)	1996-12-31
AU1653592A (en)	1992-11-17
FI925702A0 (fi)	1992-12-15
BR9205234A (pt)	1993-07-27
IE921211A1 (en)	1992-10-21
NO300545B1 (no)	1997-06-16
PL297358A1 (en)	1994-01-10
DK0537318T3 (da)	1996-07-01
JPH06500339A (ja)	1994-01-13

Legal Events

Date	Code	Title
1999-01-26	FF	Patent granted
1999-09-22	KB	Patent renewed
2003-01-12	MM9K	Patent not in force due to non-payment of renewal fees

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