NO874928L - Anvendelse av malonsyrederivatforbindelser for aa gi oekende avlinger. - Google Patents

Anvendelse av malonsyrederivatforbindelser for aa gi oekende avlinger. Download PDF

Info

Publication number: NO874928L
Authority: NO; Norway
Prior art keywords: substituted; ring system; alkyl; unsubstituted; aromatic
Prior art date: 1986-03-31

Application number

NO874928A

Other languages

English (en)

Norwegian (no)

Other versions

NO874928D0 (no

Inventor

Charles David Fritz

Anson Richard Cooke

David Treadway Manning

Thomas Neil Wheeler

James Joseph Cappy

Barbara Auxier Moore

Original Assignee

Rhone Poulenc Bv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-03-31

Filing date

1987-11-26

Publication date

1988-01-29

1987-03-30 Priority claimed from PCT/US1987/000647 external-priority patent/WO1987005897A2/en

1987-11-26 Application filed by Rhone Poulenc Bv filed Critical Rhone Poulenc Bv

1987-11-26 Publication of NO874928D0 publication Critical patent/NO874928D0/no

1988-01-29 Publication of NO874928L publication Critical patent/NO874928L/no

Links

-1 MALONIC ACID DERIVATIVE COMPOUNDS Chemical class 0.000 title claims description 172
230000001965 increasing effect Effects 0.000 title claims description 53
150000001875 compounds Chemical class 0.000 claims description 138
125000000217 alkyl group Chemical group 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 65
241000196324 Embryophyta Species 0.000 claims description 63
238000002360 preparation method Methods 0.000 claims description 63
238000000034 method Methods 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 58
125000006574 non-aromatic ring group Chemical group 0.000 claims description 52
125000004432 carbon atom Chemical group C* 0.000 claims description 45
125000001424 substituent group Chemical group 0.000 claims description 45
125000005842 heteroatom Chemical group 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 42
229910052736 halogen Inorganic materials 0.000 claims description 37
150000002367 halogens Chemical class 0.000 claims description 37
125000003342 alkenyl group Chemical group 0.000 claims description 33
125000006684 polyhaloalkyl group Polymers 0.000 claims description 33
229920006395 saturated elastomer Polymers 0.000 claims description 32
229910052717 sulfur Inorganic materials 0.000 claims description 32
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 31
150000002431 hydrogen Chemical class 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 30
125000004414 alkyl thio group Chemical group 0.000 claims description 29
125000004122 cyclic group Chemical group 0.000 claims description 29
125000001188 haloalkyl group Chemical group 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 27
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
125000004104 aryloxy group Chemical group 0.000 claims description 24
125000004423 acyloxy group Chemical group 0.000 claims description 23
125000003435 aroyl group Chemical group 0.000 claims description 23
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 22
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 22
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
244000068988 Glycine max Species 0.000 claims description 21
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 21
125000005110 aryl thio group Chemical group 0.000 claims description 21
125000000623 heterocyclic group Chemical group 0.000 claims description 20
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 19
101150065749 Churc1 gene Proteins 0.000 claims description 19
102100038239 Protein Churchill Human genes 0.000 claims description 19
125000002252 acyl group Chemical group 0.000 claims description 18
125000002837 carbocyclic group Chemical group 0.000 claims description 18
235000021307 Triticum Nutrition 0.000 claims description 17
125000004442 acylamino group Chemical group 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 17
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 17
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 13
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 11
244000046052 Phaseolus vulgaris 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
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 11
125000005164 aryl thioalkyl group Chemical group 0.000 claims description 11
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
235000010469 Glycine max Nutrition 0.000 claims description 9
125000005354 acylalkyl group Chemical group 0.000 claims description 9
125000006196 aroyl alkyl group Chemical group 0.000 claims description 9
125000005160 aryl oxy 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
235000013399 edible fruits Nutrition 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
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000004945 acylaminoalkyl group Chemical group 0.000 claims description 7
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 7
125000004103 aminoalkyl group Chemical group 0.000 claims description 7
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000000676 alkoxyimino group Chemical group 0.000 claims description 5
125000005277 alkyl imino group Chemical group 0.000 claims description 5
125000001118 alkylidene group Chemical group 0.000 claims description 5
230000003698 anagen phase Effects 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
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
125000005194 alkoxycarbonyloxy 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
125000005239 aroylamino group Chemical group 0.000 claims description 4
125000005333 aroyloxy 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
125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 4
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 4
125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 4
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
125000005252 haloacyl group Chemical group 0.000 claims description 4
125000005638 hydrazono group Chemical group 0.000 claims description 4
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 4
125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 4
229920001282 polysaccharide Polymers 0.000 claims description 4
239000005017 polysaccharide Substances 0.000 claims description 4
125000005031 thiocyano group Chemical group S(C#N)* 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
235000007238 Secale cereale Nutrition 0.000 claims description 3
240000003768 Solanum lycopersicum Species 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000000033 alkoxyamino group Chemical group 0.000 claims description 3
125000005138 alkoxysulfonyl 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
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
125000005133 alkynyloxy group Chemical group 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims description 3
150000004676 glycans Chemical class 0.000 claims description 3
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
125000005208 trialkylammonium group Chemical group 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
241000218631 Coniferophyta Species 0.000 claims description 2
235000001950 Elaeis guineensis Nutrition 0.000 claims description 2
244000127993 Elaeis melanococca Species 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
235000018290 Musa x paradisiaca Nutrition 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
244000269722 Thea sinensis Species 0.000 claims description 2
235000009470 Theobroma cacao Nutrition 0.000 claims description 2
244000299461 Theobroma cacao Species 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 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
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
125000000232 haloalkynyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [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
235000013616 tea Nutrition 0.000 claims description 2
125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims 5
125000005242 carbamoyl alkyl group Chemical group 0.000 claims 5
125000005041 acyloxyalkyl group Chemical group 0.000 claims 4
125000003282 alkyl amino group Chemical group 0.000 claims 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 2
125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims 2
150000003009 phosphonic acids Chemical class 0.000 claims 2
241001269524 Dura Species 0.000 claims 1
240000004658 Medicago sativa Species 0.000 claims 1
241000209056 Secale Species 0.000 claims 1
244000098338 Triticum aestivum Species 0.000 claims 1
240000008042 Zea mays Species 0.000 claims 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims 1
235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
125000000477 aza group Chemical group 0.000 claims 1
125000005243 carbonyl alkyl group Chemical group 0.000 claims 1
235000005822 corn Nutrition 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
125000005292 haloalkynyloxy group Chemical group 0.000 claims 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
239000007787 solid Substances 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
238000005481 NMR spectroscopy Methods 0.000 description 27
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000004480 active ingredient Substances 0.000 description 18
241000209140 Triticum Species 0.000 description 17
239000007921 spray Substances 0.000 description 17
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
239000000047 product Substances 0.000 description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
230000000694 effects Effects 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
238000012360 testing method Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
125000004429 atom Chemical group 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
241000219823 Medicago Species 0.000 description 10
230000000638 stimulation Effects 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000010992 reflux Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
108090000913 Nitrate Reductases Proteins 0.000 description 8
229930002875 chlorophyll Natural products 0.000 description 8
235000019804 chlorophyll Nutrition 0.000 description 8
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 8
239000000706 filtrate Substances 0.000 description 8
238000004519 manufacturing process Methods 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
239000002253 acid Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 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
125000001841 imino group Chemical group [H]N=* 0.000 description 6
229910052698 phosphorus Inorganic materials 0.000 description 6
230000008635 plant growth Effects 0.000 description 6
229910052709 silver Inorganic materials 0.000 description 6
239000004094 surface-active agent Substances 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000013504 Triton X-100 Substances 0.000 description 5
229920004890 Triton X-100 Polymers 0.000 description 5
240000006677 Vicia faba Species 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 5
125000004430 oxygen atom Chemical group O* 0.000 description 5
230000001850 reproductive effect Effects 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
238000003756 stirring Methods 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
OMUPQCXITFAUCB-UHFFFAOYSA-N 4,5-dichloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=C(Cl)C=C1N OMUPQCXITFAUCB-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
238000004458 analytical method Methods 0.000 description 4
125000002619 bicyclic group Chemical group 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
WGVYNZHLGPPMHJ-UHFFFAOYSA-N ethyl 1-[(4-bromo-2-methylphenyl)carbamoyl]cyclobutane-1-carboxylate Chemical compound C=1C=C(Br)C=C(C)C=1NC(=O)C1(C(=O)OCC)CCC1 WGVYNZHLGPPMHJ-UHFFFAOYSA-N 0.000 description 4
238000003306 harvesting Methods 0.000 description 4
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 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
230000001105 regulatory effect Effects 0.000 description 4
230000004044 response Effects 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 4
VLBCTILSUMRRIV-UHFFFAOYSA-N 1-[(4,5-dichloro-2-methylphenyl)carbamoyl]cyclopropane-1-carboxylic acid Chemical compound CC1=CC(Cl)=C(Cl)C=C1NC(=O)C1(C(O)=O)CC1 VLBCTILSUMRRIV-UHFFFAOYSA-N 0.000 description 3
GYIFQIIXFNIGSW-UHFFFAOYSA-N 2-methoxy-3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoic acid Chemical compound COC(C(O)=O)C(=O)OC(C)(C)C GYIFQIIXFNIGSW-UHFFFAOYSA-N 0.000 description 3
FVGBDIRMDCYICO-UHFFFAOYSA-N 3-(4-bromo-2-methylanilino)-3-oxopropanoic acid Chemical compound CC1=CC(Br)=CC=C1NC(=O)CC(O)=O FVGBDIRMDCYICO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
JQJNXJOEBFECBG-UHFFFAOYSA-N CCOC(=O)C1(C(O)=O)C=C1 Chemical compound CCOC(=O)C1(C(O)=O)C=C1 JQJNXJOEBFECBG-UHFFFAOYSA-N 0.000 description 3
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GOQZGKXDEIFQSS-UHFFFAOYSA-N ethyl 3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoate Chemical compound CCOC(=O)C(OC)C(=O)NC1=CC(Cl)=CC(Cl)=C1 GOQZGKXDEIFQSS-UHFFFAOYSA-N 0.000 description 1
NEGQZYYDIHYHMQ-UHFFFAOYSA-N ethyl 3-(4-chloroanilino)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NC1=CC=C(Cl)C=C1 NEGQZYYDIHYHMQ-UHFFFAOYSA-N 0.000 description 1
DVIGICXZLWQQCP-UHFFFAOYSA-N ethyl 3-(4-fluoroanilino)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NC1=CC=C(F)C=C1 DVIGICXZLWQQCP-UHFFFAOYSA-N 0.000 description 1
XAXORBKAARNPRH-UHFFFAOYSA-N ethyl 3-methylperoxy-3-oxopropanoate Chemical compound C(CC(=O)OCC)(=O)OOC XAXORBKAARNPRH-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
125000005291 haloalkenyloxy group Chemical group 0.000 description 1
RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
208000006278 hypochromic anemia Diseases 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
230000002015 leaf growth Effects 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 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
IQBWTCHGQZRPPP-UHFFFAOYSA-N methyl 3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoate Chemical compound COC(=O)C(OC)C(=O)NC1=CC(Cl)=CC(Cl)=C1 IQBWTCHGQZRPPP-UHFFFAOYSA-N 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
239000005645 nematicide Substances 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
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000009048 phenolic acids Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
230000000243 photosynthetic effect Effects 0.000 description 1
230000008121 plant development Effects 0.000 description 1
239000005648 plant growth regulator Substances 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
150000004804 polysaccharides Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 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
230000002265 prevention Effects 0.000 description 1
238000012545 processing Methods 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
238000009790 rate-determining step (RDS) Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000010076 replication Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000012109 statistical procedure Methods 0.000 description 1
239000000126 substance 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
238000012546 transfer Methods 0.000 description 1
230000014616 translation Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
230000009105 vegetative growth Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO874928A 1986-03-31 1987-11-26 Anvendelse av malonsyrederivatforbindelser for aa gi oekende avlinger. NO874928L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US84643586A	1986-03-31	1986-03-31
US1714987A	1987-03-04	1987-03-04
PCT/US1987/000647 WO1987005897A2 (en)	1986-03-31	1987-03-30	Use of malonic acid derivative compounds for increasing crop yield

Publications (2)

Publication Number	Publication Date
NO874928D0 NO874928D0 (no)	1987-11-26
NO874928L true NO874928L (no)	1988-01-29

Family

ID=27360726

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO874928A NO874928L (no)	1986-03-31	1987-11-26	Anvendelse av malonsyrederivatforbindelser for aa gi oekende avlinger.

Country Status (2)

Country	Link
DK (1)	DK623687A (da)
NO (1)	NO874928L (da)

1987
- 1987-11-26 NO NO874928A patent/NO874928L/no unknown
- 1987-11-27 DK DK623687A patent/DK623687A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK623687D0 (da)	1987-11-27
NO874928D0 (no)	1987-11-26
DK623687A (da)	1988-01-26

Publication	Publication Date	Title
KR950002854B1 (ko)	1995-03-27	상승적 식물 생장 조절제 조성물
AU614488B2 (en)	1991-09-05	Synergistic plant growth regulator compositions
KR970001472B1 (ko)	1997-02-06	3-디플루오로 메틸 피라졸 카르복사미드 살균제
WO1987005898A2 (en)	1987-10-08	Use of malonic acid derivative compounds for retarding plant growth
KR910000253B1 (ko)	1991-01-23	제초제 및 식물 생장 조절 특성을 갖는 아실시클로헥산디온과 그의 옥심 에테르의 제조방법
EP0126713A2 (de)	1984-11-28	Cyclohexandion-carbonsäurederivate mit herbizider und das Pflanzenwachstum regulierender Wirkung
JPS6310749A (ja)	1988-01-18	Ｎ−ベンジル２−（４−フルオル−３−トリフルオルメチルフエノキシ）ブタン酸アミド及びそれを含有する除草剤
SU1169516A3 (ru)	1985-07-23	Способ борьбы с нежелательной растительностью
AU7284387A (en)	1987-10-20	Use of malonic acid derivative compounds for increasing crop yield
EP0156773B1 (de)	1989-09-06	Cyclohexenon-carbonsäurederivate mit herbizider und das Pflanzenwachstum regulierender Wirkung
US4556411A (en)	1985-12-03	Benzothiazole derivatives for plant growth and development modification
SU965355A3 (ru)	1982-10-07	Способ получени производных амидов 1,2,3-тиадиазол-5-карбоновой кислоты (его варианты)
US3427146A (en)	1969-02-11	Phenoxypyridazines as herbicides
RU2054255C1 (ru)	1996-02-20	Циклогексановые производные и гербицидная композиция
HU182905B (en)	1984-03-28	Compositions for the plant growth regulation containing substituted benzazolyl-thio-alkancarboxylic acid derivatives
EP0262428B1 (en)	1991-08-14	Hydantoin derivatives and herbicides containing the derivatives as an active ingredient
NO874928L (no)	1988-01-29	Anvendelse av malonsyrederivatforbindelser for aa gi oekende avlinger.
JPH07173141A (ja)	1995-07-11	新規ピリミジン誘導体及び除草、植調剤
DD257572A5 (de)	1988-06-22	Verfahren zur steigerung des ernteertrages
CA2035024C (en)	2001-05-29	Novel glyoxylates and herbicidal and plant growth regulant activity of glyoxylates
JPS6344739B2 (da)	1988-09-06
NZ219815A (en)	1990-11-27	Malonic acid derivatives as plant growth retardants
US4289527A (en)	1981-09-15	Plant growth regulating perfluoroacyl arylthioureido isoindolediones
HU182561B (en)	1984-02-28	Herbicide compositions containing 2-phenyl-5,6-dihydro-4-pyron derivatives and process for producing the active agents
JPH04257576A (ja)	1992-09-11	チオパラコン酸誘導体、それらを含む除草剤組成物及びそれらを用いる除草方法