NO742668L - - Google Patents
Info
- Publication number
- NO742668L NO742668L NO742668A NO742668A NO742668L NO 742668 L NO742668 L NO 742668L NO 742668 A NO742668 A NO 742668A NO 742668 A NO742668 A NO 742668A NO 742668 L NO742668 L NO 742668L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- alkyl group
- hydrogen
- compound according
- sodium
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 13
- 239000011591 potassium Substances 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 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 claims description 11
- 230000008635 plant growth Effects 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 239000005864 Sulphur Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052744 lithium Inorganic materials 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- CROOPQURPKJTOH-UHFFFAOYSA-N COC(=O)P(O)(O)=O.C(C)[Na] Chemical group COC(=O)P(O)(O)=O.C(C)[Na] CROOPQURPKJTOH-UHFFFAOYSA-N 0.000 claims description 6
- NOSMQIYCWDWLIL-UHFFFAOYSA-N COC(=O)P(O)(O)=O.C[Na] Chemical group COC(=O)P(O)(O)=O.C[Na] NOSMQIYCWDWLIL-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052788 barium Inorganic materials 0.000 claims description 6
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 5
- BGYPJLADNCZNGX-UHFFFAOYSA-N methoxycarbonylphosphonic acid Chemical group COC(=O)P(O)(O)=O BGYPJLADNCZNGX-UHFFFAOYSA-N 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- YPJQMKNLYYYMOM-UHFFFAOYSA-N diazanium;methyl phosphonatoformate Chemical group [NH4+].[NH4+].COC(=O)P([O-])([O-])=O YPJQMKNLYYYMOM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- DFHAXXVZCFXGOQ-UHFFFAOYSA-K trisodium phosphonoformate Chemical group [Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O DFHAXXVZCFXGOQ-UHFFFAOYSA-K 0.000 claims description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- FUKBGYXHGNWHFP-UHFFFAOYSA-L [Na+].[Na+].COP(O)(=O)C([O-])=O.COP(O)(=O)C([O-])=O Chemical group [Na+].[Na+].COP(O)(=O)C([O-])=O.COP(O)(=O)C([O-])=O FUKBGYXHGNWHFP-UHFFFAOYSA-L 0.000 claims description 3
- ICSHUPSUGZYMFT-UHFFFAOYSA-L disodium;carboxy(ethoxy)phosphinate Chemical group [Na+].[Na+].CCOP([O-])(=O)C(O)=O.CCOP([O-])(=O)C(O)=O ICSHUPSUGZYMFT-UHFFFAOYSA-L 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 239000011572 manganese Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- FFCBLGDWKJHVHG-UHFFFAOYSA-N CSC(=O)P(O)(O)=O.C[Na] Chemical group CSC(=O)P(O)(O)=O.C[Na] FFCBLGDWKJHVHG-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 45
- 239000000243 solution Substances 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 230000012010 growth Effects 0.000 description 13
- -1 alkali metal salt Chemical class 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000005342 ion exchange Methods 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 5
- 239000004552 water soluble powder Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 235000014441 Prunus serotina Nutrition 0.000 description 4
- 241001278079 Salix nigra Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000002373 plant growth inhibitor Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- XLWYFERKZNPRDR-UHFFFAOYSA-N CSC(=S)P(O)(O)=O.C(C)[Na] Chemical compound CSC(=S)P(O)(O)=O.C(C)[Na] XLWYFERKZNPRDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000220225 Malus Species 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 240000008027 Akebia quinata Species 0.000 description 2
- 235000007756 Akebia quinata Nutrition 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 241000735234 Ligustrum Species 0.000 description 2
- 241000220296 Malus sp. Species 0.000 description 2
- RHUODGTXEYJWLD-UHFFFAOYSA-N NC(=O)OP(O)=O Chemical class NC(=O)OP(O)=O RHUODGTXEYJWLD-UHFFFAOYSA-N 0.000 description 2
- 240000008296 Prunus serotina Species 0.000 description 2
- 241001412173 Rubus canescens Species 0.000 description 2
- 241000921305 Salix sp. Species 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- VITRIUYHBVKBDH-UHFFFAOYSA-N methyl dimethoxyphosphorylformate Chemical compound COC(=O)P(=O)(OC)OC VITRIUYHBVKBDH-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 231100001184 nonphytotoxic Toxicity 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical class OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000013138 pruning Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- 235000003097 Artemisia absinthium Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- RACPNRHEFWJTJX-UHFFFAOYSA-N CSC(=O)P(O)(O)=O.C(C)[Na] Chemical compound CSC(=O)P(O)(O)=O.C(C)[Na] RACPNRHEFWJTJX-UHFFFAOYSA-N 0.000 description 1
- 244000201986 Cassia tora Species 0.000 description 1
- 235000014552 Cassia tora Nutrition 0.000 description 1
- 235000007516 Chrysanthemum 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
- 244000075634 Cyperus rotundus Species 0.000 description 1
- 235000016854 Cyperus rotundus Nutrition 0.000 description 1
- 235000012827 Digitaria sp Nutrition 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 244000078127 Eleusine coracana Species 0.000 description 1
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
- 241000555682 Forsythia x intermedia Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- 241000218998 Salicaceae Species 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000218636 Thuja Species 0.000 description 1
- 240000003243 Thuja occidentalis Species 0.000 description 1
- 235000008109 Thuja occidentalis Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 241001506773 Xanthium sp. Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical compound BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 description 1
- UHURJXXAXXMMLW-UHFFFAOYSA-N but-3-en-1-yl radical Chemical compound [CH2]CC=C UHURJXXAXXMMLW-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- NWVQNVFVBMFHHI-UHFFFAOYSA-N ethoxy(methoxycarbonyl)phosphinic acid Chemical compound CCOP(O)(=O)C(=O)OC NWVQNVFVBMFHHI-UHFFFAOYSA-N 0.000 description 1
- NOJFJZZMRDSOLM-UHFFFAOYSA-N ethyl diethoxyphosphorylformate Chemical compound CCOC(=O)P(=O)(OCC)OCC NOJFJZZMRDSOLM-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000005094 fruit set Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- MLJVWFGPQCOELH-UHFFFAOYSA-N methyl diethoxyphosphorylformate Chemical compound CCOP(=O)(OCC)C(=O)OC MLJVWFGPQCOELH-UHFFFAOYSA-N 0.000 description 1
- BMPFQUFNKSYHME-UHFFFAOYSA-N methyl diethoxyphosphorylmethanedithioate Chemical compound CCOP(=O)(OCC)C(=S)SC BMPFQUFNKSYHME-UHFFFAOYSA-N 0.000 description 1
- YHCFHHZOOKYAEO-UHFFFAOYSA-N methylazanium;methyl phosphonatoformate Chemical compound [NH3+]C.[NH3+]C.COC(=O)P([O-])([O-])=O YHCFHHZOOKYAEO-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- ILRVASBWNRYBFD-UHFFFAOYSA-K trisodium phosphonoformate hexahydrate Chemical compound O.O.O.O.O.O.[Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O ILRVASBWNRYBFD-UHFFFAOYSA-K 0.000 description 1
- 238000009736 wetting Methods 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Planteveksthemmende middel Plant growth inhibitor
Oppfinnelsen angår carboxyfosfonater og anvendelse avThe invention relates to carboxyphosphonates and their use
disse som planteveksthemmende middel. Bruk av forskjellige carbamoylfosfonater for å kontrollere plantevekst er kjent. Således an- these as a plant growth inhibitor. The use of various carbamoyl phosphonates to control plant growth is known. Thus an-
går f.eks. US patentskrift nr. 3 627 507 og tysk tilgjengeliggjort patentsøknad nr. 2 040 367 bruk av carbamoylfosfonater for å kontrol- goes e.g. US Patent No. 3,627,507 and German Published Patent Application No. 2,040,367 use of carbamoyl phosphonates to control
lere plantevekst. I ingen av disse publikasjoner er imidlertid carboxyfosfonater ifølge oppfinnelsen foreslått. I Berichte 57, clay plant growth. However, in none of these publications are carboxyphosphonates according to the invention proposed. In Berichte 57,
1023 (1924) er trinatriumcarboxyfosfonat og dessuten sink-, mangan-, kobber-, bly- og sølvsalter beskrevet. I denne publikasjon er imidlertid ikke angitt noe angående bruk av disse salter. I US patentskrift nr. 3 033 891 er beskrevet estere og salter av alkyl-thiocarbonylfosfonsyre, men i denne publikasjon er det ikke antydet at disse forbindelser skulle kunne virke kontrollerende på plante- 1023 (1924), trisodium carboxyphosphonate and also zinc, manganese, copper, lead and silver salts are described. In this publication, however, nothing is indicated regarding the use of these salts. US Patent No. 3,033,891 describes esters and salts of alkyl-thiocarbonylphosphonic acid, but in this publication it is not suggested that these compounds could have a controlling effect on plant
veksten.the growth.
Ifølge oppfinnelsen kan plantevekst kontrolleres ved til-førsel til plantene av forbindelser med én av de følgende formler: According to the invention, plant growth can be controlled by supplying the plants with compounds with one of the following formulas:
hvori M betyr hydrogen, natrium, lithium, kalium, kalsium, magnesium, sink, mangan, barium eller R betyr M, alkyl.med 1-8 carbonatomer som eventuelt kan være sub-, stituert med et klor-, brom- fluor- eller jodatom, en alkenylgruppe med 3-8 carbonatomer eller in which M means hydrogen, sodium, lithium, potassium, calcium, magnesium, zinc, manganese, barium or R means M, alkyl.with 1-8 carbon atoms which may optionally be substituted, substituted with a chlorine, bromo-fluorine or iodine atom, an alkenyl group of 3-8 carbon atoms or
hvori X betyr oxygen eller svovel, Y betyr oxygen eller svovel, forutsatt at når Y betyr svovel, betyr X svovel, og når X betyr svovel, kan R ikke betyr hydrogen, wherein X means oxygen or sulphur, Y means oxygen or sulphur, provided that when Y means sulphur, X means sulphur, and when X means sulphur, R cannot mean hydrogen,
A betyr klor eller methyl, B betyr klor eller methyl, n betyr 0 eller 1, og m betyr 0 eller 1, A means chlorine or methyl, B means chlorine or methyl, n means 0 or 1, and m means 0 or 1,
R-^betyr hydrogen, en alkylgruppe med 1-4 carbonatomer eller en hydroxyalkylgruppe med 2-4 carbonatomer, R-^ means hydrogen, an alkyl group with 1-4 carbon atoms or a hydroxyalkyl group with 2-4 carbon atoms,
R2betyr hydrogen, en alkylgruppe med 1-4 carbonatomer eller en hydroxyalkylgruppe med 2-4 carbonatomer, R2 means hydrogen, an alkyl group with 1-4 carbon atoms or a hydroxyalkyl group with 2-4 carbon atoms,
R^betyr hydrogen, en alkylgruppe med 1-4 carbonatomer eller en hydroxyalkylgruppe med 2-4 carbonatomer, og R^ means hydrogen, an alkyl group of 1-4 carbon atoms or a hydroxyalkyl group of 2-4 carbon atoms, and
R 4 betyr hydrogen eller en- .alkylgruppe med 1-12 carbonatomer, forutsatt at det samlede antall carbonatomer i R-^, R2/R3 og R^er under 16, og R 4 means hydrogen or an alkyl group with 1-12 carbon atoms, provided that the total number of carbon atoms in R-^, R 2/R 3 and R^ is less than 16, and
Rg betyr en alkylgruppe med 1-6 carbonatomer, en alkenylgruppe med 3-4 carbonatomer eller benzyl. Rg means an alkyl group of 1-6 carbon atoms, an alkenyl group of 3-4 carbon atoms or benzyl.
Av forbindelsene med formel I er de forbindelser hvori R betyr en alkylgruppe med 1-4 carbonatomer eller M hvor M betyr natrium eller kalium, foretrukne. Innen denne gruppe av foretrukne forbindelser kan nevnes trinatriumcarboxyfosfonat, dinatriumethy1-carboxyfosfonat og dinatriummethylcarboxyfosfonat. Of the compounds of formula I, the compounds in which R means an alkyl group with 1-4 carbon atoms or M where M means sodium or potassium are preferred. Within this group of preferred compounds, mention may be made of trisodium carboxyphosphonate, disodium ethyl carboxyphosphonate and disodium methylcarboxyphosphonate.
De ovenfor beskrevne aktive forbindelser kan tilføres til planter for å regulere planteveksten. Uttrykket "tilføres til planter" som anvendt heri er ment å omfatte både en direkte tilførsel til plantene og en tilførsel til jorden hvori plantene vokser. The active compounds described above can be added to plants to regulate plant growth. The term "applied to plants" as used herein is intended to include both a direct application to the plants and an application to the soil in which the plants grow.
Av de ovenfor beskrevne forbindelser er de forbindelser nye hvori M betyr lithium, kalium, kalsium, magnesium, barium eller Of the compounds described above, the compounds in which M stands for lithium, potassium, calcium, magnesium, barium or
og R betyr M eller en alkylgruppe med 1-8 carbonatomer som kan være substituert med et klor-, brom-, fluor- eller jodatom, en alkenylgruppe med 3-8 carbonatomer, eller and R means M or an alkyl group with 1-8 carbon atoms which may be substituted with a chlorine, bromine, fluorine or iodine atom, an alkenyl group with 3-8 carbon atoms, or
hvori A betyr klor eller methyl, og B betyr klor where A means chlorine or methyl, and B means chlorine
eller methyl, n betyr 0 eller 1 og m betyr 0 eller 1.or methyl, n means 0 or 1 and m means 0 or 1.
Foretrukne forbindelser ifølge oppfinnelsen innbefatter også de forbindelser med formel II hvori Preferred compounds according to the invention also include those compounds of formula II in which
R betyr M, en alkylgruppe med 1-4 carbonatomer eller benzyl, M betyr hydrogen, natrium, kalium eller ammonium, R means M, an alkyl group with 1-4 carbon atoms or benzyl, M means hydrogen, sodium, potassium or ammonium,
Rc- betyr en alkylgruppe med 1-3 carbonatomer,Rc- means an alkyl group with 1-3 carbon atoms,
X betyr oxygen eller svovel, forutsatt at når X betyr svovel, kan R ikke bety hydrogen, og X means oxygen or sulphur, provided that when X means sulphur, R cannot mean hydrogen, and
Y betyr oxygen.Y stands for oxygen.
Av de mest foretrukne forbindelser ifølge oppfinnelsen kan nevnes methoxycarbonylfosfonsyre, diammoniummethoxycarbonylfosfonat, ethylnatriummethoxycarbonylfosfonat og methylnatriummethoxycarbonylfosfonat. Of the most preferred compounds according to the invention, mention may be made of methoxycarbonylphosphonic acid, diammonium methoxycarbonylphosphonate, ethyl sodium methoxycarbonylphosphonate and methylsodium methoxycarbonylphosphonate.
De forbindelser ifølge oppfinnelsen med formelenThe compounds according to the invention with the formula
er nye, hvori Z betyr oxygen eller svovel og R og M har den ovenfor angitte betydning, Rg. betyr M eller R^idet R^har den betydning som er angitt ovenfor, forutsatt'at..,, (a) når Z betyr S, kan R ikke are new, in which Z means oxygen or sulfur and R and M have the above meaning, Rg. means M or R^where R^has the meaning set forth above, provided that..,, (a) when Z means S, R cannot
bety hydrogen og Rg ikke M, (b) når Rg betyr M, kan R eller Mmeans hydrogen and Rg not M, (b) when Rg means M, R or M can
ikke bety hydrogen, og (c) når Rfi betyr M og Z betyr 0, kan Mdoes not mean hydrogen, and (c) when Rfi means M and Z means 0, M can
ikke bety hydrogen, sink, mangan eller natrium.do not mean hydrogen, zinc, manganese or sodium.
Forbindelsene med formelen I kan fremstilles ved alkalisk hydrolyse av det egnede substituerte alkylcarboxyfosfonat. Hydro-lysen utføres ved å tilbakeløpsdestillere utgangsmaterialet i van-dige oppløsninger inneholdende 2 eller 3 ekvivalenter med alkali-metallhydroxyd. Straks et alkalimetallsalt er blitt dannet, kan andre salter dannes ved omsetning med metallsalter av andre syrer eller ved hjelp av vanlig ionebytting. Det bør bemerkes at de ifølge oppfinnelsen anvendbare forbindelsers aktivitet beror på carboxyfosfonatanion. Den nøyaktige type av kationer som anionet er assosiert med, er av liten betydning. The compounds of formula I can be prepared by alkaline hydrolysis of the appropriate substituted alkylcarboxyphosphonate. Hydrolysis is carried out by refluxing the starting material in aqueous solutions containing 2 or 3 equivalents of alkali metal hydroxide. As soon as an alkali metal salt has been formed, other salts can be formed by reaction with metal salts of other acids or by means of ordinary ion exchange. It should be noted that the activity of the compounds usable according to the invention depends on the carboxyphosphonate anion. The exact type of cation with which the anion is associated is of little importance.
For formel II hvori R og M betyr hydrogen, kan alkoxycar-bonylfosfonsyrene og alkylthiocarbonylfosfonsyrene med formel II lett fremstilles ved omsetning av dialkylalkoxycarbonylfosfonatene eller alkylthiocarbonylfosf onater med hydrogen j-odid. Salter av disse syrer kan fremstilles ved å omsette syrene med énreller to ekvivalenter av en .base'med det egnede kation. For formula II in which R and M are hydrogen, the alkoxycarbonylphosphonic acids and the alkylthiocarbonylphosphonic acids of formula II can be easily prepared by reacting the dialkylalkyloxycarbonylphosphonates or alkylthiocarbonylphosphonates with hydrogen iodide. Salts of these acids can be prepared by reacting the acids with one or two equivalents of a base with the appropriate cation.
Dialkylalkoxycarbonylfosfonatene og alkylthiocarbonylfosf onatene som er forløpere for forbindelsene ifølge oppfinnelsen, kan fremstilles ved hjelp av en rekke forskjellige metoder som er beskrevet innen litteraturen, som av Nylen i Chem. Ber. 57, 1023 The dialkylalkoxycarbonylphosphonates and alkylthiocarbonylphosphonates which are precursors to the compounds according to the invention can be prepared using a number of different methods which are described in the literature, such as by Nylen in Chem. Pray. 57, 1023
(1924), og av Reetz og medarbeidere i JACS 77'3813 (1955). Fremgangsmåten omfatter behandling av et egnet trialkylfosfit med et klorformiat eller thiolklorformiat. (1924), and by Reetz and co-workers in JACS 77'3813 (1955). The method comprises treatment of a suitable trialkyl phosphite with a chloroformate or thiol chloroformate.
I de nedenstående eksempler er fremstillingen av forbindelsene ifølge oppfinnelsen nærmere beskrevet. In the examples below, the preparation of the compounds according to the invention is described in more detail.
Eksempel 1.Example 1.
Ved anvendelse av metoden ifølge Nylen og beskrevet i Ber., 57B, 1023 (1924), ble en oppløsning av 21 deler triethyl-carboxyfosfonat i 60 deler vann som inneholdt 24 deler 50 % natriumhydroxyd, tilbakeløpsdestillert i 2 timer. Oppløsningen ble avkjølt over natten. Ved filtrering av reaksjonsblandingen ble det oppnådd 4,7 deler av produktet som var trinatriumcarboxyfosfonathexahydrat, sm.p. >250° C,<v>RBr= 1560, 1530 cm"<1>. Using the method according to Nylen and described in Ber., 57B, 1023 (1924), a solution of 21 parts of triethyl carboxyphosphonate in 60 parts of water containing 24 parts of 50% sodium hydroxide was refluxed for 2 hours. The solution was cooled overnight. By filtering the reaction mixture, 4.7 parts of the product were obtained which was trisodium carboxyphosphonate hexahydrate, m.p. >250° C,<v>RBr= 1560, 1530 cm"<1>.
På lignende måte ved anvendelse av det egnede metall-hydroxyd kan de følgende forbindelser fremstilles: In a similar way, using the appropriate metal hydroxide, the following compounds can be prepared:
, hvori R betyr M som på sin, side betyr lithium, , where R stands for M which in turn stands for lithium,
kalium, kalsium, magnesium, sink, mangan eller barium. potassium, calcium, magnesium, zinc, manganese or barium.
Triammoniumsaltene kan ikke fremstilles direkte ved hydrolyse av trialkylesterne. De må erholdes ved å føre en opp-løsning inneholdende trinatriumcarboxyfosfonat gjennom en ionebyttekolonne som på forhånd er blitt behandlet med det egnede ammoniumkation. The triammonium salts cannot be produced directly by hydrolysis of the trialkyl esters. They must be obtained by passing a solution containing trisodium carboxyphosphonate through an ion exchange column which has been previously treated with the appropriate ammonium cation.
På denne måte kan de følgende forbindelser fremstilles: In this way, the following compounds can be prepared:
hvor M betyr N<H>4, (<CH>3)NH3, (C4H9)NH3, (C^H^N^, (CH3)2N<H>2, (CH3)NH2EC12H25) , (CH3)3NH, (C^H^NH, (CH3)4Nf(CH3) 3N (C^Hg) , (CH3)3N(C12H25), (C2H4OH)NH3, (HOCH2CH2CH2CH2)NH3, (CH3)NH2(CH2CH2-OH) eller (CH3) N (CH2CH2OH) 3'. where M means N<H>4, (<CH>3)NH3, (C4H9)NH3, (C^H^N^, (CH3)2N<H>2, (CH3)NH2EC12H25) , (CH3)3NH, (C^H^NH, (CH3)4Nf(CH3) 3N (C^Hg) , (CH3)3N(C12H25), (C2H4OH)NH3, (HOCH2CH2CH2CH2)NH3, (CH3)NH2(CH2CH2-OH) or ( CH 3 ) N (CH 2 CH 2 OH) 3'.
Eksempel 2Example 2
En oppløsning av 15,5 deler ammoniumethylcarbamoylfos-fonat og 16 deler 50 % natriumhydroxyd i 50 deler vann ble tilbake-løpsdestillert i 2 timer. Oppløsningen ble avkjølt og inndampet til tørrhet under vakuum, og det ble erholdt dinatriumethylcarboxyfosfonat, sm.p. >300° C, Vren = 1580 (C=0), .1080 (P-0~), 1040 (P-OCH2CH3) cm"1. A solution of 15.5 parts of ammonium ethylcarbamoylphosphonate and 16 parts of 50% sodium hydroxide in 50 parts of water was refluxed for 2 hours. The solution was cooled and evaporated to dryness under vacuum to give disodium ethylcarboxyphosphonate, m.p. >300° C, Vren = 1580 (C=0), .1080 (P-0~), 1040 (P-OCH 2 CH 3 ) cm"1.
Eksempel 3Example 3
8,0 deler 50 % natriumhydroxyd ble langsomt tilsatt til8.0 parts of 50% sodium hydroxide was slowly added to
en oppløsning av 8,5 deler trimethylcarboxyfosfonat i 50 deler vann. Oppløsningen ble tilbakeløpsdestillert i 1 time, avkjølt og. oppløsningsmidlet fjernet under vakuum, og det ble erholdt 10,6 a solution of 8.5 parts of trimethylcarboxyphosphonate in 50 parts of water. The solution was refluxed for 1 hour, cooled and the solvent removed under vacuum to give 10.6
deler dinatriummethylcarboxyfosfonat, sm.p.<>>250° C, vren=1<5>80, 1080 (P~0~) , 1050 (P-0CH3) cm"<1.>parts disodium methylcarboxyphosphonate, m.p.<>>250° C, vren=1<5>80, 1080 (P~0~) , 1050 (P-0CH3) cm"<1.>
På lignende måte ved anvendelse av det egnede metall-hydroxyd og fosfonatester kan de følgende forbindelser fremstilles: In a similar way, using the appropriate metal hydroxide and phosphonate esters, the following compounds can be prepared:
Ved å føre en oppløsning av et egnet dinatriumalkylcar-boxyfosfonat gjennom en egnet ionebyttekolonne som på forhånd er blitt behandlet med det egnede ammoniumkation, kan de følgende forbindelser fremstilles: By passing a solution of a suitable disodium alkylcarboxyphosphonate through a suitable ion exchange column which has been previously treated with the suitable ammonium cation, the following compounds can be prepared:
Eksempel 4 Example 4
30 deler vannfritt hydrogenjodid ble satt til en omrørt oppløsning av 14,8 deler dimethylmethoxycarbonylfosfonat og 100 deler methylenklorid ved en temperatur på fra -5 til +5° C. Reaksjonsblandingen ble deretter oppvarmet til værelsetemperatur, hvoretter den ble omrørt over natten. Underlaget som ble dannet, ble fraskilt og inndampet under redusert trykk, og det ble erholdt 6,7 deler methoxycarbonylfosfonsyre. Nmr-spektrumet (dmso-dg) viste ingen P-0-CH3-dublett, men beholdt COOCH3-signalet. Det infrarøde 30 parts of anhydrous hydrogen iodide were added to a stirred solution of 14.8 parts of dimethylmethoxycarbonylphosphonate and 100 parts of methylene chloride at a temperature of from -5 to +5° C. The reaction mixture was then warmed to room temperature, after which it was stirred overnight. The substrate that formed was separated and evaporated under reduced pressure, and 6.7 parts of methoxycarbonylphosphonic acid were obtained. The Nmr spectrum (dmso-dg) showed no P-O-CH3 doublet but retained the COOCH3 signal. The infrared
0 _10 _1
spektrum viste gruppen C-OCH3 ved 17 0 0 cm<-1>og gruppen P- 0 ved 1100 cm"<1>. spectrum showed the group C-OCH3 at 17 0 0 cm<-1> and the group P- 0 at 1100 cm"<1>.
Ved å erstatte dimethylmethoxycarbonylfosfonatet ifølge eksempel 1 med det egnede dimethylalkoxycarbonyl- eller alkylthiocarbonylfosf onat kan de følgende forbindelser fremstilles: By replacing the dimethylmethoxycarbonyl phosphonate according to example 1 with the suitable dimethyl alkoxycarbonyl or alkylthiocarbonyl phosphonate, the following compounds can be prepared:
hvori R5betyr CH2=CHCH2CH2, CH2=CHC<H>2,CH3CH2, (CH3)2CHCH2, CH3CH2CH2CH2CH2CH2, C6H5CH2 eller CH3C<H>2<C>H2CH2CH2Eksempel 5 ) 3 deler av methoxycarbonylfosfonsyr som er produktet ifølge eksempel lj ble under omrøring satt til 50 deler ammonium-hydroxyd som inneholdt et par isstykker. Den avkjølte oppløsning ble omrørt i 15 minutter og ble deretter inndampet under redusert trykk, og det ønskede diammoniummethoxycarbonylfosfonat, sm.p. in which R5 means CH2=CHCH2CH2, CH2=CHC<H>2,CH3CH2, (CH3)2CHCH2, CH3CH2CH2CH2CH2CH2, C6H5CH2 or CH3C<H>2<C>H2CH2CH2 Example 5 ) 3 parts of methoxycarbonylphosphonic acid which is the product according to example lj were added while stirring to 50 parts of ammonium hydroxide which contained a couple of ice cubes. The cooled solution was stirred for 15 minutes and then evaporated under reduced pressure to give the desired diammonium methoxycarbonylphosphonate, m.p.
157° d, ble erholdt'.157° d, was obtained'.
Ved å erstatte ammoniumhydroxydet ifølge eksempel 2 med 1 eller 2 ekvivalenter av den egnede base eller ved vanlig ionebytting kunne dé følgende salter på lignende måte fremstilles: By replacing the ammonium hydroxide according to example 2 with 1 or 2 equivalents of the suitable base or by ordinary ion exchange, the following salts could be prepared in a similar way:
Eksempel 6 Example 6
En blanding av 15,0 deler natriumjodid og 9,4 deler di-methylmethoxycarbonylf osf onat på 20 deler 2-butanon ble oppvarmet i 1 time til 60° C. Blandingen ble avkjølt og filtrert, og det ble erholdt 8,0 deler av det ønskede methylnatriummethoxycarbonylfosfonat, sm.p. 183° d. A mixture of 15.0 parts of sodium iodide and 9.4 parts of dimethylmethoxycarbonyl phosphate in 20 parts of 2-butanone was heated for 1 hour at 60° C. The mixture was cooled and filtered, and 8.0 parts of the desired methyl sodium methoxycarbonylphosphonate, m.p. 183° d.
Eksempel 7Example 7
EthylnatriummethoxycarbonylfosfonatEthyl sodium methoxycarbonylphosphonate
En oppløsning av 5,9 deler diethylmethoxycarbonylfosfonat og 4,5 deler natriumjodid ble i 50 deler tetrahydrofuran omrørt i 60 timer ved værelsetemperatur. Den erholdte blanding ble filtrert, og det ble erholdt 3,5 deler av det ønskede ethylnatriummethoxycar-bonylf osf onat , sm.p. 123° d. A solution of 5.9 parts of diethylmethoxycarbonylphosphonate and 4.5 parts of sodium iodide in 50 parts of tetrahydrofuran was stirred for 60 hours at room temperature. The resulting mixture was filtered, and 3.5 parts of the desired ethyl sodium methoxycarbonyl phosphate were obtained, m.p. 123° d.
På lignende måte kan de følgende salter fremstilles fra dialkylalkoxycarbonylfosfonatene: In a similar manner, the following salts can be prepared from the dialkyl alkoxycarbonyl phosphonates:
Eksempel 8 Example 8
Når en vandig oppløsning av ethylnatriummethoxycarbonylfosfonat føres gjennom en egnet sur ionebyttekolonne, fåes ethyl-hydrogenmethoxycarbonylfosfonat. When an aqueous solution of ethyl sodium methoxycarbonylphosphonate is passed through a suitable acidic ion exchange column, ethyl hydrogen methoxycarbonylphosphonate is obtained.
På lignende måte kan de følgende hydrogenfosfonater fremstilles fra de egnede salter. In a similar manner, the following hydrogen phosphonates can be prepared from the appropriate salts.
. Eksempel 9. . Example 9.
En forsiktig nøytralisering av en vandig oppløsning av methylhydrogenmethoxycarbonylfosfonat med 1 ekvivalent ammonium-hydroxyd fører til methylammoniummethoxycarbonylfosfonatet. A careful neutralization of an aqueous solution of methylhydrogenmethoxycarbonylphosphonate with 1 equivalent of ammonium hydroxide leads to the methylammonium methoxycarbonylphosphonate.
På lignende måte kan de følgende fosfonatsalter fremstilles fra det egnede hydrogenfosfonat og den egnede base. In a similar manner, the following phosphonate salts can be prepared from the appropriate hydrogen phosphonate and the appropriate base.
Disse salter kan også fremstilles direkte fra natriumsaltene ved hjelp av vanlige ionebyttemetoder. These salts can also be prepared directly from the sodium salts using common ion exchange methods.
Eksempel 10Example 10
Ved anvendelse av fremgangsmåten beskrevet i US patent nr. 3 033 891 kan de følgende natriumsalter fremstilles. By using the method described in US patent no. 3,033,891, the following sodium salts can be prepared.
Eksempel 11 Example 11
EthylhydrogenmethylthiocarbonylfosfonatEthylhydrogenmethylthiocarbonylphosphonate
Ved å lede en vandig oppløsning av ethylnatriummethylthio-carbonylfosfonat fremstilt som beskrevet i US patentskrift nr. 3 033 891, gjennom en egnet sur ionebytteharpiks fåes ethhylhydro-genmethylthiocarbonylfosfonat. By passing an aqueous solution of ethyl sodium methylthiocarbonylphosphonate prepared as described in US Patent No. 3,033,891, through a suitable acidic ion exchange resin, ethylhydrogenmethylthiocarbonylphosphonate is obtained.
På lignende måte kan de følgende hydrogenfosfonater fremstilles fra de egnede salter. ■ In a similar manner, the following hydrogen phosphonates can be prepared from the appropriate salts. ■
... Eksempel 12 ... Example 12
MethylkaliumbenzylthiocarbonylfosfonatMethyl potassium benzylthiocarbonylphosphonate
Ved forsiktig nøytralisering av en vandig oppløsning av methylhydrogenbenzylthiocarbonylf os f onat med 1 ekvivalent kalium-hydroxyd fåes methylkaliumbenzylthiocarbonylfos.fonat. By careful neutralization of an aqueous solution of methylhydrogenbenzylthiocarbonylphosphonate with 1 equivalent of potassium hydroxide, methylpotassium benzylthiocarbonylphosphonate is obtained.
På lignende måte kan de følgende salter fremstilles fra det egnede hydrogenfosfonat og den egnede base. In a similar manner, the following salts can be prepared from the appropriate hydrogen phosphonate and the appropriate base.
Disse forbindelser kan også'fremstilles direkte fra natriumsaltene ved hjelp av vanlige ionebyttemetoder. These compounds can also be prepared directly from the sodium salts by conventional ion exchange methods.
Eksempel 13Example 13
E thylnatrium-( methylthio)- thiocarbonylfosfonatEthyl sodium-(methylthio)-thiocarbonylphosphonate
Til en oppløsning av 2,3 deler diethyl-(methylthio)-thio-carbonylf osf onat i 50 deler tørt tetrahydrofuran ble 1,5 deler natriumjodid tilsatt. Oppløsningen ble omrørt i 18 timer ved værelsetemperatur og deretter oppvarmet på dampbad i 0,5 time. Det. ønskede oransjefarvede ethylnatrium-(methylthio)-thiocarbonylfosfonat ble deretter filtrert og hadde et smeltepunkt på 288°d med spaltning. To a solution of 2.3 parts of diethyl-(methylthio)-thiocarbonylphosphonate in 50 parts of dry tetrahydrofuran, 1.5 parts of sodium iodide were added. The solution was stirred for 18 hours at room temperature and then heated on a steam bath for 0.5 hour. The. desired orange-colored ethyl sodium (methylthio)-thiocarbonylphosphonate was then filtered and had a melting point of 288°d with cleavage.
Eksempel 14Example 14
Ethylhydrogen-( methylthio)- thiocarbonylfosfonatEthylhydrogen-(methylthio)-thiocarbonylphosphonate
Når en vandig oppløsning av ethylnatrium-(methylthio)-thiocarbonylfosfonat ledes gjennom en egnet sur ionebyttekolonne, fåes ethylhydrogen-(methylthio)-thiocarbonylfosfonat. When an aqueous solution of ethyl sodium (methylthio)-thiocarbonylphosphonate is passed through a suitable acidic ion exchange column, ethylhydrogen-(methylthio)-thiocarbonylphosphonate is obtained.
På lignende måte kan ved bruk av de egnede fosfonatsalter de følgende forbindelser fremstilles. In a similar way, using the suitable phosphonate salts, the following compounds can be prepared.
Eksempel 15 Example 15
Methylbarium-( methylthio)- thiocarbonylfosfonatMethylbarium-(methylthio)-thiocarbonylphosphonate
Når methylhydrogen-(methylthio)-thiocarbonylfosfonat nøy-traliseres forsiktig med 0,5 ekvivalent bariumcarbonat, fåes methylbarium- (methylthio)-thiocarbonylfosfonat. When methylhydrogen-(methylthio)-thiocarbonylphosphonate is carefully neutralized with 0.5 equivalent of barium carbonate, methylbarium-(methylthio)-thiocarbonylphosphonate is obtained.
På lignende måte kan de følgende fosfonatsalter fremstilles fra det egnede hydrogenfosfonat og den egnede base. In a similar manner, the following phosphonate salts can be prepared from the appropriate hydrogen phosphonate and the appropriate base.
Disse salter kan også fremstilles direkte fra natriumsaltene ved hjelp av vanlige ionebyttemetoder. These salts can also be prepared directly from the sodium salts using common ion exchange methods.
Forbindelsene og saltene ifølge oppfinnelsen anvendes for å påvirfø veksten av planter. Forbindelsene og saltene ifølge oppfinnelsen er spesielt nyttige for å hindre knoppbristing og for å hemme veksten av treaktige planter. Forbindelsene og saltene ifølge oppfinnelsen kan således anvendes innen slike områder som kraftledningsgater hvor det er spesielt ønskelig med lavtvoksende og langsomtvoksende vegetasjon. The compounds and salts according to the invention are used to stimulate the growth of plants. The compounds and salts according to the invention are particularly useful for preventing bud burst and for inhibiting the growth of woody plants. The compounds and salts according to the invention can thus be used in areas such as power line streets where low-growing and slow-growing vegetation is particularly desirable.
Foruten at de er verdifulle som planteveksthemmende midler, kan forbindelsene ifølge oppfinnelsen også anvendes for å kontrol- .'. lere blomstringen, fruktsettingen og farven for epler og andre fruk-ter. De er nyttige for å kontrollere veksten og blomstringen av dekorative plantesorter, som krysantemum og azaleaer. Besides being valuable as plant growth inhibitors, the compounds according to the invention can also be used to control learn the flowering, fruiting and color of apples and other fruits. They are useful for controlling the growth and flowering of ornamental plants, such as chrysanthemums and azaleas.
Forbindelsene ifølge oppfinnelsen kan også anvendes for å forlenge hviletiden for flerårige planter og derved beskytte ut-sprungne knopper mot frostbeskadigelse. Dette kan være spesielt viktig for beskyttelse av blomsterknopper som i enkelte år kan springe tidlig ut og ødelegges av lave temperaturer. Når forbindelsene ifølge oppfinnelsen tilføres til planter på det stadium når det følgende års knopper begynner å' utvikles eller er under utvik-ling, gir en markert hemming av knoppbristing den følgende vår og en sterkt nedsatt vekst. The compounds according to the invention can also be used to extend the rest period for perennial plants and thereby protect sprouted buds against frost damage. This can be particularly important for the protection of flower buds, which in some years can spring out early and be destroyed by low temperatures. When the compounds according to the invention are added to plants at the stage when the following year's buds begin to develop or are under development, a marked inhibition of bud burst results in the following spring and a greatly reduced growth.
For å vise de foreliggende forbindelsers og salters vekst-hemmende aktivitet er nedenfor en del forsøksresultater gjengitt. In order to show the growth-inhibiting activity of the present compounds and salts, some experimental results are reproduced below.
Ifølge et forsøk ble prøveforbindelsen tilført i et opp-løsningsmiddel sammen med et fuktemiddel og et fuktighetsbevarende middel til bomullsplanter (på fem-stadiet, innbefattende kimblad), krypbønner (i det annet trebladstadium, ekspanderende blad), orme-vindel (i fire-bladstadiumet, innbefattende kimblad), krokfrø According to an experiment, the test compound was added in a solvent together with a wetting agent and a humectant to cotton plants (at the five-leaf stage, including cotyledons), creeping beans (at the second three-leaf stage, expanding leaves), wormwood (at the four-leaf stage , including cotyledon), hook seed
(Xanthium sp., i fire-bladstadiumet innbefattende kimblad), Cassia tora (i tre-bladstadiumet, innbefattende kimblad), Cyperus rotundus (i tre- til fem-bladstadiumet), fingerhirse/(Digitaria sp., i to-blad-stadiumet), hønsehirse (Echinochloa sp., i to-bladstadiumet), vildhavre (Avena fatua, i et-bladstadiumet), hvete (i to-bladstadiumet) , mais (i tre-bladstadiumet), soyabønner (to kimblad), ris (i to-bladstadiumet), og durra (i tre-bladstadiumet). (Xanthium sp., in the four-leaf stage including cotyledons), Cassia tora (in the three-leaf stage, including cotyledons), Cyperus rotundus (in the three- to five-leaf stage), finger millet/(Digitaria sp., in the two-leaf stage ), millet (Echinochloa sp., in the two-leaf stage), wild oats (Avena fatua, in the one-leaf stage), wheat (in the two-leaf stage), corn (in the three-leaf stage), soybeans (two cotyledons), rice (in the two-leaf stage), and sorghum (in the three-leaf stage).
Behandlede planter og kontrollplanter ble holdt i et drivhus i 16 dager, hvoretter alle sorter ble sammenlignet med kontroll-. plantene og .visuelt bedømt for å fastslå virkningen av behandlingen. Treated plants and control plants were kept in a greenhouse for 16 days, after which all cultivars were compared with controls. the plants and .visually judged to determine the effect of the treatment.
Ved et annet forsøk ble prøveforbindelsen tilført i et lignende oppløsningsniiddel til potter med liguster (Ligustrum sp.), pil (Salix sp.), forsythia (Forsythioa sp.), Arbor Vitae (Thuja sp.) og eple- (Malus sp.). Planten ble holdt i et drivhus. Virkningen på plantene ble bedømt 1 uke og 4 uker etter tilførselen. In another experiment, the test compound was added in a similar dilution ratio to pots with privet (Ligustrum sp.), willow (Salix sp.), forsythia (Forsythioa sp.), Arbor Vitae (Thuja sp.) and apple (Malus sp.) . The plant was kept in a greenhouse. The effect on the plants was assessed 1 week and 4 weeks after application.
Forbindelsen tilført i et lignende oppløsningsmiddel til. potter med sorte Valentine-bønner . (Phaseolus vulgaris cv. Black Valentine), epler (Malus sp.) og pil (Salix sp.). Plantene ble holdt i et drivhus, og virkningen på plantene ble bedømt etter .til-førselen som angitt. The compound added in a similar solvent to. pots of black Valentine beans. (Phaseolus vulgaris cv. Black Valentine), apples (Malus sp.) and willows (Salix sp.). The plants were kept in a greenhouse and the effect on the plants was judged according to the supply as indicated.
Virkningen på plantene (ovenfor) er angitt ved hjelp av et tall og en bokstav. Tallet beskriver virkningsgraden og vari-erer fra null til ti idet null angir ingen virkning og ti 100 % virkning. Bokstaven angir typen av virkning som følger: C = klorose-necrose, D = bladfall, G = hemmet vekst, H = formvirk-ning (misformning), I = øket klorofyllmengde, P = endeknoppbeska-digelse, X = aksilærstimulering, 8Q<X>= øket fruktstørrelse, The effect on the plants (above) is indicated using a number and a letter. The number describes the degree of effectiveness and varies from zero to ten, with zero indicating no effectiveness and ten 100% effectiveness. The letter indicates the type of effect as follows: C = chlorosis-necrosis, D = leaf fall, G = inhibited growth, H = shape effect (deformation), I = increased amount of chlorophyll, P = terminal bud damage, X = axillary stimulation, 8Q<X >= increased fruit size,
8Y = løsnende knopper eller blomster8Y = loosening buds or flowers
54 fotnote: For betegnelsene "8Q" og "8Y" angir tallet ikke virkningsgraden (enhver prosentuell økning i fruktstørrel-sen er angitt ved 8Q). 54 footnote: For the designations "8Q" and "8Y" the number does not indicate the degree of effectiveness (any percentage increase in fruit size is indicated by 8Q).
Med uttrykket "planteveksthemmende middel" som anvendt heri er ment å betegne et middel som når det tilføres til en plante eller dens omgivelser, vil senke veksthastigheten for planten. Dette innebærer også en forsinket knoppskyting eller en forlengelse av hvileperioden. The term "plant growth inhibitor" as used herein is intended to denote an agent which, when added to a plant or its surroundings, will reduce the growth rate of the plant. This also involves a delayed bud shoot or an extension of the rest period.
Forbindelsene og saltene ifølge oppfinnelsen kan tilføres ved pådusjing på bladverket eller til jorden for å hemme plantenes veksthastighet eller for å påvirke blomstringen og fruktsettingen. The compounds and salts according to the invention can be added by spraying on the foliage or to the soil to inhibit the growth rate of the plants or to affect flowering and fruiting.
Forbindelsene ifølge oppfinnelsen tilføres fortrinnsvis i form av en dusj på bladverket eller på treverket i hvileperioden inntil avrenning, selv 'om en påføring av mindre volum også kan gi god virkning. The compounds according to the invention are preferably applied in the form of a shower on the foliage or on the wood during the rest period until runoff, although an application of a smaller volume can also have a good effect.
Forbindelsene og saltene ifølge oppfinnelsen har et meget vidt anvendelsesområde og kan tilføres Sn eller flere ganger etter brukerens ønske. De kan således tilføres våren kort tid før det forventes at den sterkeste plantevekst vil finne sted, for derved å hemme planteveksten. De kan tilføres senere under voksesesongen like etter beskjæring for å hemme planteveksten. De kan også til-føres når årets vekst har opphørt (om sensommeren, om høsten eller om vinteren) med det resultat at de behandlede planter vil befinne seg i hviletilstand det påfølgende år, mens ubehandlede planter vil spire og vokse. Hvis blomstringen og fruktsettingen skal forandres, foretas behandlingen før, under eller kort tid etter blomstringen. The compounds and salts according to the invention have a very wide range of applications and can be added to Sn or several times according to the user's wishes. They can thus be added in the spring shortly before the strongest plant growth is expected to take place, thereby inhibiting plant growth. They can be added later in the growing season just after pruning to inhibit plant growth. They can also be added when the year's growth has ceased (in late summer, autumn or winter), with the result that the treated plants will be in a dormant state the following year, while untreated plants will germinate and grow. If flowering and fruit set are to be changed, the treatment is carried out before, during or shortly after flowering.
Det vil forståes at den tilførte mengde er avhengig av de sorter som skal behandles og de ønskede resultater. Vanligvis anvendes 0,2 5 - 2 0 kg/ha, men også høyere eller lavere mengder kan It will be understood that the added quantity depends on the varieties to be treated and the desired results. Usually 0.25 - 20 kg/ha is used, but higher or lower amounts can also be used
i enkelte tilfeller gi den ønskede virkning.in some cases produce the desired effect.
Nyttige materialformer med., forbindelsene og saltene ifølge oppfinnelsen kan fremstilles på vanlige måter. Av slike nyttige materialformer kan nevnes støv, granulater, pellets, opp-løsninger, suspensjoner, emulsjoner, fukte-pulvere og emulgerbare konsentrater etc. En rekke av disse kan tilføres direkte. Sprøyt-bare materialformer kan fortynnes med egnede midler og anvendes i sprøytevolum på fra noen få liter til flere tusen liter pr. dekar. Sterkt konsentrerte blandinger anvendes hovedsakelig som utgangs-materialer for videre opparbeidelse. De materialformer som anvendes for tilførsel til plantene, inneholder grovt regnet 1-99 vekt% aktiv bestanddel eller aktive bestanddeler og minst et av a) 0,1 - 20 % overflateaktivt middel eller midler og b) 5 - 99 % fast'eller flytende fortynningsmiddel eller f ortynningsmidler.. Useful material forms with., the compounds and the salts according to the invention can be prepared in usual ways. Such useful material forms include dust, granules, pellets, solutions, suspensions, emulsions, wetting powders and emulsifiable concentrates, etc. A number of these can be supplied directly. Sprayable material forms can be diluted with suitable agents and used in spray volumes of from a few liters to several thousand liters per acres. Highly concentrated mixtures are mainly used as starting materials for further processing. The forms of material used for supply to the plants roughly contain 1-99% by weight active ingredient or active ingredients and at least one of a) 0.1 - 20% surfactant or agents and b) 5 - 99% solid or liquid diluent or f thinners..
De vil nærmere bestemt inneholde disse bestanddeler i de følgende omtrentlige forholdsvise mengder: More precisely, they will contain these components in the following approximate relative quantities:
Lavere eller høyere mengder med aktive bestanddel kan følgelig anvendes, avhengig av den beregnede anvendelse og forbin-delsens fysikalske egenskaper. Høyere forhold mellom overflateaktivt middel og aktiv bestanddel er av og til ønsket og kan erhol-,'. des ved å tilsette et overflateaktivt middel til materialet eller ved blanding i tank. På lignende måte kan store mengder olje eller fuktighetsbevarende midler tilføres til materialet eller ved blanding i tank. Lower or higher amounts of active ingredient can therefore be used, depending on the intended use and the physical properties of the compound. Higher ratios between surfactant and active ingredient are sometimes desired and can be obtained. des by adding a surface-active agent to the material or by mixing in a tank. In a similar way, large quantities of oil or humectants can be added to the material or by mixing in a tank.
Typiske faste fortynningsmidler er beskrevet i Watkins og medarbeidere, "Handbook of Insecticide Dust Diluents and Carriers", 2nd. Edri., Dorland Books, Caldwell, N.J. De sterkere absorberende fortynningsmidler foretrekkes for fuktbare pulvere, og de tyngre fortynningsmidler for støv. Typiske flytende fortynningsmidler og oppløsningsmidler er beskrevet i Marsden, "Solvents Guide", 2nd, Edn. Interscience, New York, 1950. En oppiøselighet under 0,1 % er foretrukket for suspensjonskonsentrater. ' Oppløsningskonsentrater bør fortrinnsvis være stabile overfor faseseparering ved 0° C. I "McCutcheon's Detergents and Emulsifiers Annual", Allured Publ. Corp., Ridgewood, New Jersey, og i Sisely og Wood, "Encyclopedia of Surface Active Agents", Chemical Publ. Co., Inc., New York, 1964, Typical solid diluents are described in Watkins et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd. Ed., Dorland Books, Caldwell, N.J. The stronger absorbent diluents are preferred for wettable powders, and the heavier diluents for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd, Edn. Interscience, New York, 1950. A solubility below 0.1% is preferred for suspension concentrates. ' Solution concentrates should preferably be stable to phase separation at 0° C. In "McCutcheon's Detergents and Emulsifiers Annual", Allured Publ. Corp., Ridgewood, New Jersey, and in Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publ. Co., Inc., New York, 1964,
er gitt lister over overflateaktive midler og anbefalte anvendelser. Alle materialformer kan inneholde mindre mengder tilsetningsmidler for å nedsette skumdannelse, sainmenbakning, korrosjon eller mikro-biologisk vekst etc. lists of surfactants and recommended applications are provided. All forms of material may contain small amounts of additives to reduce foam formation, sainmenbaking, corrosion or micro-biological growth etc.
Fremgangsmåtene for fremstilling av slike blandinger er velkjente. Oppløsninger fremstilles ganske enkelt ved å blande bestanddelene. Findelte, faste blandinger fremstilles ved blanding og, vanligvis, maling f.eks. i en hammermølle eller jetmølle. Suspensjoner fremstilles ved våtmaling, se f.eks. US patentskrift nr. 3 060 084. Granulater og pellets kan fremstilles ved å sprøyte det aktive materiale på på forhånd dannede kornformige bærematerialer eller ved hjelp av agglomereringsteknikk. Se J.E. Browning., "Agglomeration", ChemicalEngineering, des. 4, 1967, s. 147ff, og "Perry's Chemical Engineer's Handbook", 4th. Edn., McGraw-Hill, The methods for preparing such mixtures are well known. Solutions are prepared simply by mixing the ingredients. Finely divided, solid mixtures are produced by mixing and, usually, grinding e.g. in a hammer mill or jet mill. Suspensions are produced by wet painting, see e.g. US Patent No. 3,060,084. Granules and pellets can be produced by spraying the active material onto previously formed granular carrier materials or by means of agglomeration techniques. See J.E. Browning., "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff, and "Perry's Chemical Engineer's Handbook", 4th. Ed., McGraw-Hill,
N.Y. 1963, s, 8-59ff. NEW. 1963, pp. 8-59ff.
For ytterligere opplysninger angående metoder for fremstilling av de forskjellige materialformer kan det f.eks. vises til US patentskrift nr. 3 235 361, US patentskrift nr. 3 627 507, For further information regarding methods for the production of the various material forms, it can e.g. refer to US Patent No. 3,235,361, US Patent No. 3,627,507,
G.C. Klingman, "Weed Control as a Science", John Wilev&Sons, Inc., New York, 1961, s. 81 - 96, og J.D. Fryer og S.A. Evans, "Weed Control Handbook", 5th Edn. Blackwell Scientific Publications, Oxford, 1968, s. 101 - 103. G. C. Klingman, "Weed Control as a Science", John Wilev&Sons, Inc., New York, 1961, pp. 81-96, and J.D. Fryer and S.A. Evans, "Weed Control Handbook", 5th Edn. Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
I de nedenstående eksempler er fremstilling av de forskjellige materialformer inneholdende forbindelsene og saltene ifølge oppfinnelsen og anvendelsen av disse nærmere beskrevet. In the examples below, the preparation of the different material forms containing the compounds and salts according to the invention and their use are described in more detail.
Eksemp el 16.Example 16.
Fuktbart pulverWettable powder
Det ble fremstilt et fuktbart pulver bestående av A wettable powder consisting of
Bestanddelene ble godt blandet, ledet gjennom en luft-mølle for erholdelse av en gjennomsnittlig partikkelstørrelse under 15 ym, igjen blandet, og siktet gjennom en US standard sikt nr. 50 (0,3 mm åpning) før pakking. The ingredients were well mixed, passed through an air mill to obtain an average particle size below 15 µm, again mixed, and sieved through a US standard #50 sieve (0.3 mm aperture) before packaging.
Alle forbindelser ifølge oppfinnelsen kan overføres til All compounds according to the invention can be transferred to
et fuktbart pulver på samme måte.a wettable powder in the same way.
15 kg av dette materiale ble blandet med 600 liter vann i et sprøyteapparat forsynt med en omrører. Blandingen ble sprøytet på et 1 hektar område med en nylig beskåret hekk om våren etter at bladene var sprunget ut. (Dusjen kan rettes direkte mot plantene eller plantenes voksested). Ved hjelp av denne behandling nedsettes veksten av plantene i hekken sterkt uten at de utsettes for 15 kg of this material was mixed with 600 liters of water in a sprayer equipped with a stirrer. The mixture was sprayed on a 1 hectare area with a newly pruned hedge in the spring after the leaves had emerged. (The shower can be aimed directly at the plants or where the plants grow). With the help of this treatment, the growth of the plants in the hedge is greatly reduced without exposing them to
alvorlig beskadigelse. Hekken kan således holdes velstelt med minimal arbeidsinnsats for å trimme hekken. serious damage. The hedge can thus be kept well-kept with minimal effort to trim the hedge.
Eksempel 17Example 17
Vannoppløselig pulverWater soluble powder
Det ble fremstilt et vannoppløselig pulver bestående av A water-soluble powder consisting of
Bestanddelene blandes og grovmales i en hammermølle slik at bare et par prosent av den aktive bestanddel har en partikkel-størrelse over 250 ym (US sikt nr. 60). Når det settes til vann under omrøring, dispergeres det grovdelte pulver til å begynne med, og deretter oppløses den aktive bestanddel slik at det ikke er nød-vendig med ytterligere omrøring under påføringen. 10 kg av dette materiale oppløses i 800 liter vann inneholdende 0,5 % av et ikke-fytotoksisk fuktemiddel. Denne blanding sprøytes fra et helikopter på et område på 1 ha under en elektrisk kraftledningsgate hvor buskvekster og trær nylig var blitt beskåret. Denne behandling hemmer veksten av svartpil (Salix nigra), svart kirsebær (Prunus serotina) og en rekke andre treplanter. The ingredients are mixed and coarsely ground in a hammer mill so that only a few percent of the active ingredient has a particle size above 250 ym (US sieve no. 60). When added to water with stirring, the coarsely divided powder is initially dispersed, and then the active ingredient dissolves so that no further stirring is necessary during application. 10 kg of this material is dissolved in 800 liters of water containing 0.5% of a non-phytotoxic wetting agent. This mixture was sprayed from a helicopter on an area of 1 ha under an electric power line where shrubs and trees had recently been pruned. This treatment inhibits the growth of black willow (Salix nigra), black cherry (Prunus serotina) and a number of other woody plants.
Eksempel 18Example 18
O ppløsningResolution
Det ble fremstilt en oppløsning bestående avA solution consisting of
Bestanddelene ble blandet, og omrørt for fremstilling av en oppløsning som kan påføres direkte eller etter fortynning med ytterligere vann. 15 liter av denne oppløsning blandes med 200 liter vann og sprøytes på sensommeren på et 1 ha område av treplanter som vokser i en kraftledningsgate. De behandlede planter fortsetter å se ut som ubehandlede planter. Det følgende år befinner imidlertid plantene seg i hviletilstand i meget lang tid, mens ubehandlede planter spirer og vokser normalt. Ved hjelp av denne behandling nedsettes således sterkt den arbeidsinnsats som er nødvendig for at plantene skal holdes på en ønsket høyde. The ingredients were mixed and stirred to produce a solution that can be applied directly or after dilution with additional water. 15 liters of this solution are mixed with 200 liters of water and sprayed in late summer on a 1 ha area of tree plants growing in a power line street. The treated plants continue to look like untreated plants. The following year, however, the plants are in a dormant state for a very long time, while untreated plants germinate and grow normally. With the help of this treatment, the work effort required to keep the plants at the desired height is thus greatly reduced.
Eksempel 19Example 19
' 01jesuspensjon' 01jesuspension
Det ble fremstilt en oljesuspensjon bestående av An oil suspension consisting of
Bestanddelene males i en sandmølle inntil de faste partikler er blitt redusert til en partikkelstørrelse under ca. 5 ym. Den erholdte tykke suspensjon kan påføres direkte, men fortrinnsvis etter at den er blitt fortynnet med olje eller emulgert i vann. The components are ground in a sand mill until the solid particles have been reduced to a particle size below approx. 5 etc. The resulting thick suspension can be applied directly, but preferably after it has been diluted with oil or emulsified in water.
1 del av denne suspensjon blandes med 1 del vann i et sprøyteapparat forsynt med en omrører, og påføres om vinteren inntil suspensjonen renner av fra barken av i hviletilsatnd forekommende treplanter som vokser under en kraftledning. De behandlede planter holder seg i hviletilsatnd i meget lang tid, hvorved planteveksten sterkt nedsettes og dessuten den arbeidsinnsats som er nødvendig for beskjæring. 1 part of this suspension is mixed with 1 part of water in a sprayer equipped with a stirrer, and applied in winter until the suspension runs off the bark of dormant trees growing under a power line. The treated plants remain dormant for a very long time, whereby plant growth is greatly reduced and also the work effort required for pruning.
Eksempel 2 0Example 2 0
Vannoppløselig pulverWater soluble powder
Det ble fremstilt et vannoppløselig pulver bestående av A water-soluble powder consisting of
Bestanddelene blandes og grovmales i en hammerraø.lle. slik at bare et par prosent av den aktive bestanddel har en partikkel-størrelse på over 250 ym (US standard sikt nr. -60) . Når det settes til vann under omrøring, dispergeres det grovdelte pulver til å begynne med, og deretter oppløses den aktive bestanddel slik at det ikke er nødvendig med ytterligere omrøring under påføringen. 10 kg av dette materiale oppløses i 800 liter vann inneholdende 0,5 % av et ikke-fytotoksisk fuktemiddel. Dette materiale sprøytes fra et helikopter på et 1 ha område under en elektrisk kraftlinje hvor buskvekster og trær nylig er blitt beskåret. Denne behandling hemmer veksten av svartpil (Salix nigra), svart kirsebær (Prunus serotina) og en rekke andre trevekster. The ingredients are mixed and coarsely ground in a hammer mill. so that only a few percent of the active ingredient has a particle size of over 250 ym (US standard sieve no. -60). When added to water with agitation, the coarse powder is initially dispersed and then the active ingredient is dissolved so that no additional agitation is required during application. 10 kg of this material is dissolved in 800 liters of water containing 0.5% of a non-phytotoxic wetting agent. This material is sprayed from a helicopter on a 1 ha area under an electric power line where shrubs and trees have recently been pruned. This treatment inhibits the growth of black willow (Salix nigra), black cherry (Prunus serotina) and a number of other trees.
De følgende forbindelser kan fremstilles i form av en vannoppløselig pulverblanding og påføres på lignende måte med lignende resultater: ethylnatriummethoxycarbonylfosfonat, methylnatriummethoxycarbonylfosfonat, methylnatriumethoxycarbonylfosfonat, ethylnatriumethoxycarbonylfosfonat, ethylnatrium-(methylthio)-carbo-nylfosfonat og methylnatrium-(ethylthio)-carbonylfosfonat. The following compounds can be prepared in the form of a water-soluble powder mixture and applied in a similar manner with similar results: ethyl sodium methoxycarbonylphosphonate, methyl sodium methoxycarbonylphosphonate, methylsodium methoxycarbonylphosphonate, ethylsodium-(methylthio)-carbonylphosphonate, and methylsodium-(ethylthio)-carbonylphosphonate.
Eksempel 21Example 21
Fuktbart pulverWettable powder
Det ble fremstilt et fuktbart pulver med sammensetningen: A wettable powder was produced with the composition:
Bestanddelene blandes, føres gjennom en luftmølle for dannelse av partikler med en gjennomsnitts størrelse på vinder 15 ym, blandes påny og siktes gjennom en US standardsikt nr. 50 (0,3 mm åpning) før. pakking. The ingredients are mixed, passed through an air mill to form particles with an average size of 15 um, mixed again and sieved through a US standard sieve No. 50 (0.3 mm opening) before. packing.
Alle faste forbindelser ifølge oppfinnelsen kan overføres til et fuktbart pulver på samme måte. 15 kg av dette materiale blandes med 600 liter vann i et sprøyteapparat forsynt med en omrører. Blandingen sprøytes på et 1 ha område av nylig beskåret hekk om.våren etter at bladene har sprunget ut. (Sprøytingen kan gjøres direkte på plantene eller på plantenes voksested). Denne behandling nedsetter sterkt veksten av planter som vokser i hekken, men beskadiges ikke alvorlig. Hekken kan således holdes velstelt med minimal arbeidsinnsats for trimming av hekken. All solid compounds according to the invention can be transferred to a wettable powder in the same way. 15 kg of this material is mixed with 600 liters of water in a sprayer equipped with a stirrer. The mixture is sprayed on a 1 ha area of recently trimmed hedges in the spring after the leaves have sprouted. (The spraying can be done directly on the plants or at the plant's growing point). This treatment greatly reduces the growth of plants growing in the hedge, but is not seriously damaged. The hedge can thus be kept well-kept with minimal work for trimming the hedge.
Eksempel 22Example 22
OppløsningResolution
Det ble fremstilt en oppløsning bestående avA solution consisting of
Bestanddelene blandes og omrøres for fremstilling av en oppløsning som kan påføres direkte eller etter fortynning med ytterligere vann. Alle tilstrekkelig oppløselige forbindelser ifølge oppfinnelsen kan overføres til en oppløsning på lignende måte. 15 liter av denne oppløsning blandes med 200 liter vann og sprøytes om sensommeren på et 1 ha område av treplanter som vokser i en kraftlinjegate. De behandlede planter fortsetter å ligne ubehandlede planter. Det påfølgende år holder imidlertid plantene seg i hviletilstand i meget lang tid, mens ubehandlede planter spirer og vokser normalt. Behandlingen nedsetter således sterkt den nødven-dige arbeidsinnsats for å holde plantene på en ønsket høyde. The ingredients are mixed and stirred to produce a solution that can be applied directly or after dilution with additional water. All sufficiently soluble compounds according to the invention can be transferred to a solution in a similar way. 15 liters of this solution are mixed with 200 liters of water and sprayed in late summer on a 1 ha area of tree plants growing in a power line street. The treated plants continue to resemble untreated plants. The following year, however, the plants remain dormant for a very long time, while untreated plants germinate and grow normally. The treatment thus greatly reduces the necessary work effort to keep the plants at a desired height.
Claims (20)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38161973A | 1973-07-23 | 1973-07-23 | |
US38162073A | 1973-07-23 | 1973-07-23 | |
US39772373A | 1973-09-17 | 1973-09-17 | |
US47453774A | 1974-05-30 | 1974-05-30 | |
US05/474,536 US3943201A (en) | 1973-07-23 | 1974-05-30 | Alkoxy carboxycarbonylphosphonic acid esters |
Publications (1)
Publication Number | Publication Date |
---|---|
NO742668L true NO742668L (en) | 1975-01-24 |
Family
ID=27541382
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO742668A NO742668L (en) | 1973-07-23 | 1974-07-22 |
Country Status (22)
Country | Link |
---|---|
JP (1) | JPS5069236A (en) |
AR (1) | AR214853A1 (en) |
BE (1) | BE817918A (en) |
BR (1) | BR7405998D0 (en) |
CH (1) | CH591209A5 (en) |
CS (1) | CS180016B2 (en) |
DD (1) | DD111789A5 (en) |
DE (1) | DE2435407A1 (en) |
DK (1) | DK395274A (en) |
FR (1) | FR2238432B1 (en) |
GB (1) | GB1469136A (en) |
HU (1) | HU171255B (en) |
IE (1) | IE39635B1 (en) |
IL (1) | IL45303A (en) |
IT (1) | IT1049202B (en) |
LU (1) | LU70581A1 (en) |
MY (1) | MY8000218A (en) |
NL (1) | NL7409943A (en) |
NO (1) | NO742668L (en) |
PL (1) | PL98264B1 (en) |
SE (1) | SE422269B (en) |
SU (1) | SU671704A3 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1144937A (en) * | 1977-12-22 | 1983-04-19 | Dke J.E. Helgstrand | Aromatic derivatives, pharmaceutical compositions and methods for combatting virus infections |
DE3607445A1 (en) * | 1986-03-07 | 1987-09-10 | Hoechst Ag | METHOD FOR PRODUCING ALKALI PHOSPHONO FORMATS |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3033891A (en) * | 1959-11-27 | 1962-05-08 | Monsanto Chemicals | Mono salts of o-hydrocarbyl-carboalkylthiol phosphonic acids |
-
1974
- 1974-06-22 HU HU74DU00000226A patent/HU171255B/en unknown
- 1974-06-22 BR BR5998/74A patent/BR7405998D0/en unknown
- 1974-06-27 SE SE7408487A patent/SE422269B/en unknown
- 1974-07-19 DD DD180007A patent/DD111789A5/xx unknown
- 1974-07-19 IL IL45303A patent/IL45303A/en unknown
- 1974-07-19 CS CS7400005165A patent/CS180016B2/en unknown
- 1974-07-22 SU SU742044846A patent/SU671704A3/en active
- 1974-07-22 IT IT25437/74A patent/IT1049202B/en active
- 1974-07-22 FR FR7425333A patent/FR2238432B1/fr not_active Expired
- 1974-07-22 LU LU70581A patent/LU70581A1/xx unknown
- 1974-07-22 JP JP49083332A patent/JPS5069236A/ja active Pending
- 1974-07-22 DK DK395274A patent/DK395274A/da unknown
- 1974-07-22 GB GB3238374A patent/GB1469136A/en not_active Expired
- 1974-07-22 BE BE146790A patent/BE817918A/en unknown
- 1974-07-22 NO NO742668A patent/NO742668L/no unknown
- 1974-07-22 AR AR254812A patent/AR214853A1/en active
- 1974-07-23 DE DE2435407A patent/DE2435407A1/en not_active Withdrawn
- 1974-07-23 CH CH1016174A patent/CH591209A5/xx not_active IP Right Cessation
- 1974-07-23 NL NL7409943A patent/NL7409943A/en unknown
- 1974-07-23 PL PL1974172929A patent/PL98264B1/en unknown
- 1974-07-23 IE IE1560/74A patent/IE39635B1/en unknown
-
1980
- 1980-12-30 MY MY218/80A patent/MY8000218A/en unknown
Also Published As
Publication number | Publication date |
---|---|
JPS5069236A (en) | 1975-06-10 |
SE422269B (en) | 1982-03-01 |
FR2238432A1 (en) | 1975-02-21 |
IE39635L (en) | 1975-01-23 |
DE2435407A1 (en) | 1975-02-13 |
SU671704A3 (en) | 1979-06-30 |
FR2238432B1 (en) | 1978-07-13 |
IT1049202B (en) | 1981-01-20 |
HU171255B (en) | 1977-12-28 |
DD111789A5 (en) | 1975-03-12 |
CH591209A5 (en) | 1977-09-15 |
CS180016B2 (en) | 1977-12-30 |
AR214853A1 (en) | 1979-08-15 |
GB1469136A (en) | 1977-03-30 |
SE7408487L (en) | 1975-01-24 |
AU7146674A (en) | 1976-01-22 |
DK395274A (en) | 1975-03-10 |
IL45303A0 (en) | 1974-10-22 |
BR7405998D0 (en) | 1975-05-13 |
BE817918A (en) | 1974-11-18 |
IE39635B1 (en) | 1978-11-22 |
MY8000218A (en) | 1980-12-31 |
NL7409943A (en) | 1975-01-27 |
LU70581A1 (en) | 1974-11-28 |
PL98264B1 (en) | 1978-04-29 |
IL45303A (en) | 1977-07-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR860002169B1 (en) | The process for preparation of trialkylsulfonium salts of n-phosphonomethyglycine | |
EP0109314B1 (en) | Aluminum n-phosphonomethylglycine and its use as a herbicide | |
US3799758A (en) | N-phosphonomethyl-glycine phytotoxicant compositions | |
NO830500L (en) | N-PHOSPHONOMETHYLGYCINE DERIVATIVES AND PROCEDURES FOR PREPARING THEREOF | |
NO141090B (en) | N-PHOSPHONE MATHYLLYCINES FOR USE AS HERBICIDES AND / OR PHYTOTOXIC | |
EP0054382B1 (en) | Triethylsulfonium salts of n-phosphonomethylglycine, production thereof, their use as plant growth regulators, herbicides and compositions containing them | |
EP0073574B1 (en) | Phosphonium salts of n-phosphonomethylglycine, preparation and compositions thereof and the use thereof as herbicides and plant growth regulants | |
DK142056B (en) | N-organo-N-phosphonomethylglycine-N-oxide compounds for use as herbicides or plant growth regulators. | |
CA1118784A (en) | Glycylmethylphosphinic acid derivatives, process for their production and use thereof | |
US4341549A (en) | Phosphonium salts of N-phosphonomethylglycine and their use as herbicides and plant growth regulants | |
US3943201A (en) | Alkoxy carboxycarbonylphosphonic acid esters | |
US4018854A (en) | Carboxyphosphonates | |
WO1983003608A1 (en) | Tetra-substituted ammonium salt of n-phosphonomethylglycine and their uses as herbicides and plant growth regulants | |
NO742668L (en) | ||
SU1486049A3 (en) | Method of controlling the growth lf farm crops | |
EP0115176B1 (en) | Stannic n-phosphonomethylglycine compounds and their use as herbicides | |
AU614730B2 (en) | Compositions including herbicidal combinations of the glyphosate type and the phenoxybenzoic type | |
HU184234B (en) | Preparations for controlling the plant growth | |
US4106923A (en) | Phosphonomethyl glycine ester anhydrides, herbicidal composition containing same and use thereof | |
NO860068L (en) | HERBICIDE COMPOUNDS AND PREPARATIONS. | |
US4033749A (en) | Alkoxycarbonylphosphonic acid derivative brush control agents | |
US4328027A (en) | Di-triethylamine salt of N,N'-bis-carboethoxymethyl-N,N'-bis-phosphonomethylurea and its use as a plant growth regulator | |
US4108626A (en) | Alkoxycarbonylphosphonic acid derivative brush control agents | |
US4095970A (en) | 2,6-Dichlorothiolbenzoates and use thereof as plant growth regulators | |
US4701211A (en) | Substituted benzyltriethylammonium salts and their use as plant growth enhancers |