CS207456B1 - herbicide means - Google Patents

herbicide means Download PDF

Info

Publication number: CS207456B1
Authority: CS; Czechoslovakia
Prior art keywords: amino; propyl; acid; salt; carboxy
Prior art date: 1976-05-17

Application number

CS320677A

Other languages

Czech (cs)

English (en)

Inventor

Walter Rupp

Manfred Finke

Hermann Bieringer

Peter Langelueddeke

Hans-Jerg Kleiner

Original Assignee

Hoechst 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.)

1976-05-17

Filing date

1977-05-16

Publication date

1981-07-31

1977-05-16 Application filed by Hoechst Ag filed Critical Hoechst Ag

1981-07-31 Publication of CS207456B1 publication Critical patent/CS207456B1/cs

Links

230000002363 herbicidal effect Effects 0.000 title claims description 8
239000004009 herbicide Substances 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 25
239000004480 active ingredient Substances 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical compound CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 26
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical group [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
CCNFQMNABFUFMN-UHFFFAOYSA-N Cl.CP(O)=O Chemical compound Cl.CP(O)=O CCNFQMNABFUFMN-UHFFFAOYSA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical class CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 5
150000007529 inorganic bases Chemical class 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
238000010494 dissociation reaction Methods 0.000 claims description 2
230000005593 dissociations Effects 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
125000003884 phenylalkyl group Chemical group 0.000 claims 1
241000196324 Embryophyta Species 0.000 abstract description 22
239000002253 acid Substances 0.000 abstract description 19
150000007513 acids Chemical class 0.000 abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
150000001408 amides Chemical class 0.000 abstract 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
125000004970 halomethyl group Chemical group 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
229910052717 sulfur Chemical group 0.000 abstract 1
239000011593 sulfur Chemical group 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
-1 2-hydroxyethoxy, 4-hydroxybutoxy Chemical group 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000011734 sodium Substances 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
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 10
238000006243 chemical reaction Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
239000000155 melt Substances 0.000 description 4
SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000005210 alkyl ammonium group Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
244000038559 crop plants Species 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 3
150000002903 organophosphorus compounds Chemical class 0.000 description 3
230000008635 plant growth Effects 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
JFTHBDBUVHRREF-UHFFFAOYSA-N 2-acetamidopropanedioic acid Chemical class CC(=O)NC(C(O)=O)C(O)=O JFTHBDBUVHRREF-UHFFFAOYSA-N 0.000 description 2
240000001592 Amaranthus caudatus Species 0.000 description 2
235000009328 Amaranthus caudatus Nutrition 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
244000075634 Cyperus rotundus Species 0.000 description 2
235000016854 Cyperus rotundus Nutrition 0.000 description 2
244000133098 Echinacea angustifolia Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
241000209082 Lolium Species 0.000 description 2
244000042664 Matricaria chamomilla Species 0.000 description 2
235000007232 Matricaria chamomilla Nutrition 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
240000006694 Stellaria media Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000010949 copper Substances 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000005131 dialkylammonium group Chemical group 0.000 description 2
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
235000014134 echinacea Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
NDRKHLDFNRVLBW-UHFFFAOYSA-N hydroxy-methyl-sulfidophosphanium Chemical compound CP(O)=S NDRKHLDFNRVLBW-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000011701 zinc Substances 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 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
IDBRULKICVRMNG-UHFFFAOYSA-N 2-amino-4-hydroxyphosphonoylbutanoic acid Chemical compound OC(=O)C(N)CCP(O)=O IDBRULKICVRMNG-UHFFFAOYSA-N 0.000 description 1
ZNVFLMYQLVSXSK-UHFFFAOYSA-N 4-[butoxy(methyl)phosphoryl]butan-2-one Chemical compound CCCCOP(C)(=O)CCC(C)=O ZNVFLMYQLVSXSK-UHFFFAOYSA-N 0.000 description 1
241000209136 Agropyron Species 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
241000743985 Alopecurus Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000219318 Amaranthus Species 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
241000339490 Brachyachne Species 0.000 description 1
244000056139 Brassica cretica Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
VSEALZMXPGYWSV-UHFFFAOYSA-N C(C)OP(=O)C=CC Chemical compound C(C)OP(=O)C=CC VSEALZMXPGYWSV-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
235000007866 Chamaemelum nobile Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000723353 Chrysanthemum Species 0.000 description 1
235000007516 Chrysanthemum Nutrition 0.000 description 1
235000005633 Chrysanthemum balsamita Nutrition 0.000 description 1
240000005250 Chrysanthemum indicum Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
235000021506 Ipomoea Nutrition 0.000 description 1
241000207783 Ipomoea Species 0.000 description 1
241000209510 Liliopsida Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
235000017945 Matricaria Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
241000209048 Poa Species 0.000 description 1
241000209049 Poa pratensis Species 0.000 description 1
241001071900 Scapanus orarius Species 0.000 description 1
235000005775 Setaria Nutrition 0.000 description 1
241000232088 Setaria <nematode> Species 0.000 description 1
241000220261 Sinapis Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
238000007059 Strecker synthesis reaction Methods 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
241001148683 Zostera marina Species 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
235000012735 amaranth Nutrition 0.000 description 1
239000004178 amaranth Substances 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000005452 bending Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GZUFHXSFPZCNJA-UHFFFAOYSA-N butoxy(methyl)phosphinic acid Chemical compound CCCCOP(C)(O)=O GZUFHXSFPZCNJA-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
OVFCVRIJCCDFNQ-UHFFFAOYSA-N carbonic acid;copper Chemical compound [Cu].OC(O)=O OVFCVRIJCCDFNQ-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
239000011646 cupric carbonate Substances 0.000 description 1
235000019854 cupric carbonate Nutrition 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
ISOLMABRZPQKOV-UHFFFAOYSA-N diethyl 2-acetamidopropanedioate Chemical compound CCOC(=O)C(NC(C)=O)C(=O)OCC ISOLMABRZPQKOV-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
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 1
239000004922 lacquer Substances 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
125000001117 oleyl group Polymers [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])=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
239000000546 pharmaceutical excipient Substances 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- C07F9/30—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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CS320677A 1976-05-17 1977-05-16 herbicide means CS207456B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH615376		1976-05-17

Publications (1)

Publication Number	Publication Date
CS207456B1 true CS207456B1 (en)	1981-07-31

Family

ID=4305116

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS320677A CS207456B1 (en)	1976-05-17	1977-05-16	herbicide means

Country Status (28)

Country	Link
US (1)	US4168963A (fr)
JP (1)	JPS52139727A (fr)
AR (1)	AR220314A1 (fr)
AT (1)	AT358315B (fr)
AU (1)	AU506817B2 (fr)
BE (1)	BE854753A (fr)
BR (1)	BR7703155A (fr)
CA (1)	CA1120052A (fr)
CS (1)	CS207456B1 (fr)
DD (1)	DD130094A5 (fr)
DE (1)	DE2717440C2 (fr)
DK (1)	DK142441B (fr)
FR (1)	FR2351598A1 (fr)
GB (1)	GB1587292A (fr)
GR (1)	GR71675B (fr)
HU (1)	HU185003B (fr)
IL (1)	IL52098A (fr)
IT (1)	IT1143658B (fr)
KE (1)	KE3264A (fr)
NL (1)	NL179866C (fr)
NZ (1)	NZ184101A (fr)
OA (1)	OA05664A (fr)
PH (1)	PH13253A (fr)
PL (1)	PL103386B1 (fr)
PT (1)	PT66555B (fr)
SE (1)	SE439416B (fr)
SU (1)	SU659069A3 (fr)
ZA (1)	ZA772828B (fr)

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CA2344659C (fr)	1998-09-23	2008-08-19	Hampshire Chemical Corp.	Sarcosinates utilises comme adjuvants du glufosinate
DE19919848A1 (de)	1999-04-30	2000-11-02	Aventis Cropscience Gmbh	Verfahren zur Herstellung von L-Phosphinothricin durch enzymatische Transaminierung mit Aspartat
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CA2662391C (fr)	2006-09-04	2015-10-06	Meiji Seika Kaisha, Ltd.	Procede de fabrication d'un acide aminophosphinylbutanoique optiquement actif
JP5336851B2 (ja)	2006-09-20	2013-11-06	ＭｅｉｊｉＳｅｉｋａファルマ株式会社	リン含有α−アミノ酸の製造法およびその製造中間体
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BR112022014971A2 (pt)	2020-01-31	2022-09-20	Basf Se	Combinação herbicida, composição, métodos para produzir uma combinação herbicida, para controlar o crescimento indesejado das plantas e para tratar ou proteger culturas e uso de combinações herbicidas
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BR112022014831A2 (pt)	2020-01-31	2022-09-27	Basf Se	Combinação de herbicidas, composição, métodos para produzir uma combinação de herbicidas, para controlar o crescimento de plantas indesejadas e para tratar ou proteger culturas e uso de uma combinação de herbicidas
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BR112022014952A2 (pt)	2020-01-31	2022-09-20	Basf Se	Combinação de herbicidas, composição, métodos de produção de combinações de herbicidas, de controle do crescimento vegetal indesejado e de tratamento ou proteção de plantas e uso da combinação de herbicidas
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1977
- 1977-04-20 DE DE2717440A patent/DE2717440C2/de not_active Expired
- 1977-05-12 NL NLAANVRAGE7705259,A patent/NL179866C/xx not_active IP Right Cessation
- 1977-05-12 ZA ZA00772828A patent/ZA772828B/xx unknown
- 1977-05-12 DD DD7700198900A patent/DD130094A5/xx unknown
- 1977-05-13 IT IT23579/77A patent/IT1143658B/it active
- 1977-05-14 GR GR53461A patent/GR71675B/el unknown
- 1977-05-16 PL PL1977198145A patent/PL103386B1/pl not_active IP Right Cessation
- 1977-05-16 AR AR267641A patent/AR220314A1/es active
- 1977-05-16 NZ NZ184101A patent/NZ184101A/xx unknown
- 1977-05-16 AT AT347477A patent/AT358315B/de not_active IP Right Cessation
- 1977-05-16 HU HU77HO1982A patent/HU185003B/hu unknown
- 1977-05-16 AU AU25151/77A patent/AU506817B2/en not_active Expired
- 1977-05-16 BR BR3155/77A patent/BR7703155A/pt unknown
- 1977-05-16 US US05/797,171 patent/US4168963A/en not_active Expired - Lifetime
- 1977-05-16 CS CS320677A patent/CS207456B1/cs unknown
- 1977-05-16 PT PT66555A patent/PT66555B/pt unknown
- 1977-05-16 CA CA000278456A patent/CA1120052A/fr not_active Expired
- 1977-05-16 DK DK212977AA patent/DK142441B/da not_active IP Right Cessation
- 1977-05-16 JP JP5555077A patent/JPS52139727A/ja active Granted
- 1977-05-16 IL IL52098A patent/IL52098A/xx unknown
- 1977-05-17 BE BE177677A patent/BE854753A/fr not_active IP Right Cessation
- 1977-05-17 SE SE7705872A patent/SE439416B/xx not_active IP Right Cessation
- 1977-05-17 PH PH19781A patent/PH13253A/en unknown
- 1977-05-17 GB GB27063/77A patent/GB1587292A/en not_active Expired
- 1977-05-17 FR FR7715031A patent/FR2351598A1/fr active Granted
- 1977-05-17 OA OA56172A patent/OA05664A/fr unknown
- 1977-05-17 SU SU772480278A patent/SU659069A3/ru active
1983
- 1983-02-25 KE KE3264A patent/KE3264A/xx unknown

Also Published As

Publication number	Publication date
AR220314A1 (es)	1980-10-31
BR7703155A (pt)	1978-01-31
PH13253A (en)	1980-02-20
KE3264A (en)	1983-03-25
GR71675B (fr)	1983-06-21
IT1143658B (it)	1986-10-22
OA05664A (fr)	1981-05-31
DK212977A (fr)	1977-11-18
JPS52139727A (en)	1977-11-21
DK142441B (da)	1980-11-03
FR2351598B1 (fr)	1984-02-17
US4168963A (en)	1979-09-25
DE2717440C2 (de)	1984-04-05
NL179866C (nl)	1986-12-01
NL179866B (nl)	1986-07-01
ATA347477A (de)	1980-01-15
PL103386B1 (pl)	1979-06-30
PL198145A1 (pl)	1978-02-27
JPS5726564B2 (fr)	1982-06-05
DD130094A5 (de)	1978-03-08
SE7705872L (sv)	1977-11-18
FR2351598A1 (fr)	1977-12-16
PT66555A (en)	1977-06-01
HU185003B (en)	1984-11-28
SE439416B (sv)	1985-06-17
CA1120052A (fr)	1982-03-16
NL7705259A (nl)	1977-11-21
IL52098A (en)	1981-02-27
IL52098A0 (en)	1977-07-31
BE854753A (fr)	1977-11-17
AU2515177A (en)	1978-11-23
AT358315B (de)	1980-09-10
SU659069A3 (ru)	1979-04-25
DK142441C (fr)	1981-08-10
DE2717440A1 (de)	1977-12-01
ZA772828B (en)	1978-04-26
NZ184101A (en)	1979-10-25
GB1587292A (en)	1981-04-01
AU506817B2 (en)	1980-01-24
PT66555B (en)	1979-01-22

Publication	Publication Date	Title
CS207456B1 (en)	1981-07-31	herbicide means
CA1140566A (fr)	1983-02-01	Composes
US4270948A (en)	1981-06-02	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
EP0014684B1 (fr)	1982-05-19	Dérivés substitués en position 2 d'acides phénoxy-5 phénylphosphoniques, procédé pour leur préparation et leur utilisation comme herbicides
IL47972A (en)	1977-12-30	N-phosphonomethylglycines and herbicidal compositions containing them
EP0073574A1 (fr)	1983-03-09	Sels de phosphonium de la N-phosphonomethylglycine, leur préparation, compositions et utilisation comme herbicides et régulateurs de la croissance des plantes
EP0281103A2 (fr)	1988-09-07	Composés de l'acide phénoxycarboxylique et herbicide les contenant comme ingrédient actif
EP0013660B1 (fr)	1983-05-18	Aminoalcoyl esters de l'acide 2-nitro-5-(ortho-chloro-para-trifluorométhylphénoxy)-benzoique, leur préparation, herbicides les contenant comme agents actifs et leur usage
US3371132A (en)	1968-02-27	O-alkyl o(s)-(n-alkoxy-n-alkyl-carbamyl methyl) phenyl (thiolo) (thiono)phosphonates
US4729781A (en)	1988-03-08	3,6-dichloro-2-methoxybenzohydroxamic acid derivatives and use as herbicidal agents
CA1088065A (fr)	1980-10-21	Agents insecticides
EP0115176B1 (fr)	1986-08-06	Composés de l'étain de la N-phosphonométhylglycine et leur utilisation comme herbicides
NZ205526A (en)	1987-04-30	Phosphorus-containing derivatives of acetic acid as herbicides and plant growth regulants
US4421547A (en)	1983-12-20	4-Hydroxy-5-isopropyl-2-methylphenyl trimethylammonium, 1-piperidine carboxylate salt of N-phosphonomethylglycine and its use as a herbicide
US4461764A (en)	1984-07-24	Pesticidal phosphoryl- and phosphinyl-thioalkyl cyclic sufones
DD252752A5 (de)	1987-12-30	Mittel zur unkrautbekaempfung
EP0038636A2 (fr)	1981-10-28	Dérivés de sulfonamide, compositions les contenant et leur préparation et utilisation
US3647850A (en)	1972-03-07	Fluorine substituted benzyl dithiocarbamates and their production and use
CA1120747A (fr)	1982-03-30	Herbicides
EP0201807B1 (fr)	1989-09-13	Dérivés oximino d'acide phosphorique, procédé pour les préparer et leur utilisation comme pesticides
CH620812A5 (en)	1980-12-31	Herbicide
DE2601447A1 (de)	1976-07-29	Cyclohexen-ester
EP0232500A2 (fr)	1987-08-19	Di- et tripeptides à la phosphinothricine N-terminale, leur procédé de préparation et leur emploi pour lutter contre les mauvaises herbes
CS210604B2 (en)	1982-01-29	Herbicide and preparation method of active substance
EP0433446B1 (fr)	1992-12-30	Composes herbicides a base d'organophosphore