DD257572A5 - Verfahren zur steigerung des ernteertrages - Google Patents
Verfahren zur steigerung des ernteertrages Download PDFInfo
- Publication number
- DD257572A5 DD257572A5 DD30126187A DD30126187A DD257572A5 DD 257572 A5 DD257572 A5 DD 257572A5 DD 30126187 A DD30126187 A DD 30126187A DD 30126187 A DD30126187 A DD 30126187A DD 257572 A5 DD257572 A5 DD 257572A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- substituted
- ring system
- unsubstituted
- compound
- Prior art date
Links
- 230000001965 increasing effect Effects 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 75
- 230000008569 process Effects 0.000 title claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 239000001257 hydrogen Substances 0.000 claims abstract description 59
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 44
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 9
- 239000011593 sulfur Substances 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 6
- -1 propargylthio, hydroxyimino Chemical group 0.000 claims description 227
- 150000001875 compounds Chemical class 0.000 claims description 153
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 241000196324 Embryophyta Species 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 58
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000004414 alkyl thio group Chemical group 0.000 claims description 30
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004122 cyclic group Chemical group 0.000 claims description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 26
- 125000004423 acyloxy group Chemical group 0.000 claims description 24
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 24
- 125000005110 aryl thio group Chemical group 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 23
- 125000003435 aroyl group Chemical group 0.000 claims description 23
- 244000068988 Glycine max Species 0.000 claims description 22
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 20
- 101150065749 Churc1 gene Proteins 0.000 claims description 20
- 102100038239 Protein Churchill Human genes 0.000 claims description 20
- 235000021307 Triticum Nutrition 0.000 claims description 20
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000004442 acylamino group Chemical group 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 19
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 16
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 13
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 13
- 229910052727 yttrium Inorganic materials 0.000 claims description 13
- 240000004658 Medicago sativa Species 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 11
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 11
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 11
- 235000010469 Glycine max Nutrition 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 235000013399 edible fruits Nutrition 0.000 claims description 10
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 9
- 125000005354 acylalkyl group Chemical group 0.000 claims description 9
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 9
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 9
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 9
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 9
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 9
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 9
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 9
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 9
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 230000001850 reproductive effect Effects 0.000 claims description 8
- 125000006196 aroyl alkyl group Chemical group 0.000 claims description 7
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
- 150000004676 glycans Chemical class 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 4
- 125000005277 alkyl imino group Chemical group 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 4
- 230000003698 anagen phase Effects 0.000 claims description 4
- 125000005239 aroylamino group Chemical group 0.000 claims description 4
- 125000005333 aroyloxy group Chemical group 0.000 claims description 4
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 4
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000004983 dialkoxyalkyl group Chemical class 0.000 claims description 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 4
- 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims description 4
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000005252 haloacyl group Chemical group 0.000 claims description 4
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
- 238000003898 horticulture Methods 0.000 claims description 4
- 125000005638 hydrazono group Chemical group 0.000 claims description 4
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 4
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 4
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 4
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 4
- 244000075850 Avena orientalis Species 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 3
- 231100000674 Phytotoxicity Toxicity 0.000 claims description 3
- 235000007238 Secale cereale Nutrition 0.000 claims description 3
- 240000003768 Solanum lycopersicum Species 0.000 claims description 3
- 244000062793 Sorghum vulgare Species 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 3
- 125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 3
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
- 235000019713 millet Nutrition 0.000 claims description 3
- 244000099147 Ananas comosus Species 0.000 claims description 2
- 235000007119 Ananas comosus Nutrition 0.000 claims description 2
- 235000007319 Avena orientalis Nutrition 0.000 claims description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 2
- 240000000385 Brassica napus var. napus Species 0.000 claims description 2
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 2
- 240000007154 Coffea arabica Species 0.000 claims description 2
- 235000001950 Elaeis guineensis Nutrition 0.000 claims description 2
- 241000219146 Gossypium Species 0.000 claims description 2
- 241000208818 Helianthus Species 0.000 claims description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims description 2
- 244000017020 Ipomoea batatas Species 0.000 claims description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 claims description 2
- 240000005561 Musa balbisiana Species 0.000 claims description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 2
- 244000061176 Nicotiana tabacum Species 0.000 claims description 2
- 241000207836 Olea <angiosperm> Species 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 240000000111 Saccharum officinarum Species 0.000 claims description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000021536 Sugar beet Nutrition 0.000 claims description 2
- 235000009470 Theobroma cacao Nutrition 0.000 claims description 2
- 244000299461 Theobroma cacao Species 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 235000021015 bananas Nutrition 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 235000020971 citrus fruits Nutrition 0.000 claims description 2
- 235000016213 coffee Nutrition 0.000 claims description 2
- 235000013353 coffee beverage Nutrition 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 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
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 8
- 244000025254 Cannabis sativa Species 0.000 claims 2
- 240000003133 Elaeis guineensis Species 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 241000209056 Secale Species 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 150000003974 aralkylamines Chemical class 0.000 claims 1
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 1
- 150000002690 malonic acid derivatives Chemical class 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 55
- 238000002360 preparation method Methods 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000005481 NMR spectroscopy Methods 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
- 230000000694 effects Effects 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 241000209140 Triticum Species 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 230000000638 stimulation Effects 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 238000000921 elemental analysis Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 229930002875 chlorophyll Natural products 0.000 description 11
- 235000019804 chlorophyll Nutrition 0.000 description 11
- 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 11
- 238000009472 formulation Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 210000003298 dental enamel Anatomy 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 108090000913 Nitrate Reductases Proteins 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000003306 harvesting Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 7
- 244000013123 dwarf bean Species 0.000 description 7
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
- 238000009331 sowing Methods 0.000 description 7
- 239000002028 Biomass Substances 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 235000021331 green beans Nutrition 0.000 description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 6
- 239000003039 volatile agent Substances 0.000 description 6
- PCHYYOCUCGCSBU-UHFFFAOYSA-N 4-bromo-2-methylaniline Chemical compound CC1=CC(Br)=CC=C1N PCHYYOCUCGCSBU-UHFFFAOYSA-N 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 5
- VSOLGZMYTKTDGN-UHFFFAOYSA-N 1-[(4-bromo-2-methylphenyl)carbamoyl]cyclobutane-1-carboxylic acid Chemical compound CC1=CC(Br)=CC=C1NC(=O)C1(C(O)=O)CCC1 VSOLGZMYTKTDGN-UHFFFAOYSA-N 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000003780 insertion Methods 0.000 description 4
- 230000037431 insertion Effects 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 4
- 239000005648 plant growth regulator Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- ADLPNADGKPULBG-UHFFFAOYSA-M 2,3-dimethoxy-3-oxopropanoate Chemical compound COC(C([O-])=O)C(=O)OC ADLPNADGKPULBG-UHFFFAOYSA-M 0.000 description 3
- AHHOEWMSBSEQAQ-UHFFFAOYSA-N 3-ethoxy-2-methoxy-3-oxopropanoic acid Chemical compound CCOC(=O)C(OC)C(O)=O AHHOEWMSBSEQAQ-UHFFFAOYSA-N 0.000 description 3
- OAKURXIZZOAYBC-UHFFFAOYSA-M 3-oxopropanoate Chemical compound [O-]C(=O)CC=O OAKURXIZZOAYBC-UHFFFAOYSA-M 0.000 description 3
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- JBDSSBMEKXHSJF-UHFFFAOYSA-M cyclopentanecarboxylate Chemical compound [O-]C(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-M 0.000 description 1
- KLMUOAOHVRFGIB-UHFFFAOYSA-N cycloprop-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)C=C1 KLMUOAOHVRFGIB-UHFFFAOYSA-N 0.000 description 1
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- 239000002037 dichloromethane fraction Substances 0.000 description 1
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- WEISAZNMMVPNTH-UHFFFAOYSA-N diethyl 2-propan-2-ylidenepropanedioate Chemical compound CCOC(=O)C(=C(C)C)C(=O)OCC WEISAZNMMVPNTH-UHFFFAOYSA-N 0.000 description 1
- JPNJEJSZSMXWSV-UHFFFAOYSA-N diethyl cyclobutane-1,1-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCC1 JPNJEJSZSMXWSV-UHFFFAOYSA-N 0.000 description 1
- NAKRHRXBVSLQAO-UHFFFAOYSA-N diethyl cyclopentane-1,1-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCCC1 NAKRHRXBVSLQAO-UHFFFAOYSA-N 0.000 description 1
- MEDTZWPBIYWHBW-UHFFFAOYSA-N diethyl cycloprop-2-ene-1,1-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)C=C1 MEDTZWPBIYWHBW-UHFFFAOYSA-N 0.000 description 1
- KYYUCZOHNYSLFV-UHFFFAOYSA-N diethyl cyclopropane-1,1-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CC1 KYYUCZOHNYSLFV-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- UUUXEDQEPAEVEZ-UHFFFAOYSA-N ethyl 1-[(3,5-dichlorophenyl)carbamoyl]cyclobutane-1-carboxylate Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C1(C(=O)OCC)CCC1 UUUXEDQEPAEVEZ-UHFFFAOYSA-N 0.000 description 1
- DBJKGNRHRBGJJZ-UHFFFAOYSA-N ethyl 2-[(4-bromo-2-methylphenyl)carbamoyl]-3-methylbut-2-enoate Chemical compound CCOC(=O)C(=C(C)C)C(=O)NC1=CC=C(Br)C=C1C DBJKGNRHRBGJJZ-UHFFFAOYSA-N 0.000 description 1
- NGDNCOUQYWVQLS-UHFFFAOYSA-N ethyl 2-carbonochloridoylbutanoate Chemical compound CCOC(=O)C(CC)C(Cl)=O NGDNCOUQYWVQLS-UHFFFAOYSA-N 0.000 description 1
- KEJSNAMXOQAILU-UHFFFAOYSA-N ethyl 3-[(4-methyl-1,3-thiazol-2-yl)amino]-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NC1=NC(C)=CS1 KEJSNAMXOQAILU-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 150000002304 glucoses Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- NQVXBAJFUZHCSB-UHFFFAOYSA-N methyl 2-(2-chloro-2-oxoethoxy)acetate Chemical compound COC(=O)COCC(Cl)=O NQVXBAJFUZHCSB-UHFFFAOYSA-N 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- GMQFXIKZIQZCRJ-UHFFFAOYSA-N n-(4,5-dichloro-2-methoxyphenyl)-2,2-dimethylpropanamide Chemical compound COC1=CC(Cl)=C(Cl)C=C1NC(=O)C(C)(C)C GMQFXIKZIQZCRJ-UHFFFAOYSA-N 0.000 description 1
- GGGRWOLCYDENKP-UHFFFAOYSA-N n-(4-chloro-2-methoxyphenyl)-2,2-dimethylpropanamide Chemical compound COC1=CC(Cl)=CC=C1NC(=O)C(C)(C)C GGGRWOLCYDENKP-UHFFFAOYSA-N 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 230000001776 parthenogenetic effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000037039 plant physiology Effects 0.000 description 1
- 235000021118 plant-derived protein Nutrition 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000013630 prepared media Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000012109 statistical procedure Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FSIDRPAUDFSNER-UHFFFAOYSA-N tert-butyl 3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)C(OC)C(=O)NC1=CC(Cl)=CC(Cl)=C1 FSIDRPAUDFSNER-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84643586A | 1986-03-31 | 1986-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD257572A5 true DD257572A5 (de) | 1988-06-22 |
Family
ID=25297924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD30126187A DD257572A5 (de) | 1986-03-31 | 1987-03-30 | Verfahren zur steigerung des ernteertrages |
Country Status (6)
| Country | Link |
|---|---|
| CN (1) | CN87103552A (es) |
| DD (1) | DD257572A5 (es) |
| ES (1) | ES2005121A6 (es) |
| GR (1) | GR870501B (es) |
| MW (1) | MW8087A1 (es) |
| ZA (1) | ZA872315B (es) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115024322A (zh) * | 2022-07-20 | 2022-09-09 | 广东省科学院微生物研究所(广东省微生物分析检测中心) | 丙二酸单乙酯在植物促生中的应用 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496737B (zh) * | 2014-12-13 | 2017-12-22 | 西安近代化学研究所 | 一种合成α‑胺甲酰基氟乙酸酯化合物的方法 |
| CN106632028B (zh) * | 2016-12-22 | 2019-01-22 | 上海再启生物技术有限公司 | 一种卡博替尼的制备方法 |
| CN107879946A (zh) * | 2017-04-25 | 2018-04-06 | 湖南比德生化科技股份有限公司 | 一种制备环丙酰胺酸的方法 |
| CN112142619B (zh) * | 2020-10-20 | 2023-01-10 | 浙江工业大学 | 一种1,1-环丙烷二羧酸酰胺类化合物及其制备方法和应用 |
-
1987
- 1987-03-30 CN CN 87103552 patent/CN87103552A/zh active Pending
- 1987-03-30 ZA ZA872315A patent/ZA872315B/xx unknown
- 1987-03-30 DD DD30126187A patent/DD257572A5/de not_active IP Right Cessation
- 1987-03-30 GR GR870501A patent/GR870501B/el unknown
- 1987-03-31 ES ES8700912A patent/ES2005121A6/es not_active Expired
- 1987-11-13 MW MW80/87A patent/MW8087A1/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115024322A (zh) * | 2022-07-20 | 2022-09-09 | 广东省科学院微生物研究所(广东省微生物分析检测中心) | 丙二酸单乙酯在植物促生中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| GR870501B (en) | 1988-07-29 |
| ES2005121A6 (es) | 1989-03-01 |
| ZA872315B (en) | 1988-11-30 |
| CN87103552A (zh) | 1988-07-06 |
| MW8087A1 (en) | 1989-08-09 |
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