LU87884A1 - Herbizid wirksame harnstoff-derivate und verfahren zur herstellung derselben - Google Patents

Herbizid wirksame harnstoff-derivate und verfahren zur herstellung derselben Download PDF

Info

Publication number: LU87884A1
Authority: LU; Luxembourg
Prior art keywords: alkyl; group; general formula; alkoxy; active ingredient
Prior art date: 1990-01-31

Application number

LU87884A

Other languages

German (de)

English (en)

Inventor

Andras Vass

Jozsef Dudas

Judit Szabo

Dezsoe Miklos

Gabor Szalontai

Zoltan Simon

Balint Nagy

Maria Kovacs

Istvan Toth

Bela Szoeke

Jozsef Nagy

Karoly Balogh

Zsolt Dombay

Csaba Pavliscsak

Angela Bartfai

Erzsebet Mile

Karoly Fodor

Original Assignee

Nehezvegyipari Kutato Intezet

Eszakmagyar Vegyimuevek

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.)

1990-01-31

Filing date

1991-01-31

Publication date

1991-07-22

1991-01-31 Application filed by Nehezvegyipari Kutato Intezet, Eszakmagyar Vegyimuevek filed Critical Nehezvegyipari Kutato Intezet

1991-07-22 Publication of LU87884A1 publication Critical patent/LU87884A1/de

Links

238000000034 method Methods 0.000 title claims description 22
238000004519 manufacturing process Methods 0.000 title description 16
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 3
239000004480 active ingredient Substances 0.000 claims description 75
239000000203 mixture Substances 0.000 claims description 73
150000001875 compounds Chemical class 0.000 claims description 70
-1 amino, piperazinyl Chemical group 0.000 claims description 47
239000000729 antidote Substances 0.000 claims description 42
ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-n-[2-oxo-2-(prop-2-enylamino)ethyl]-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 claims description 24
230000002363 herbicidal effect Effects 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 12
YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
WFVUIONFJOAYPK-SDNWHVSQSA-N (z)-n-(1,3-dioxolan-2-ylmethoxy)benzenecarboximidoyl cyanide Chemical compound C=1C=CC=CC=1C(/C#N)=N/OCC1OCCO1 WFVUIONFJOAYPK-SDNWHVSQSA-N 0.000 claims description 8
OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
239000008187 granular material Substances 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
239000004563 wettable powder Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
150000005005 aminopyrimidines Chemical class 0.000 claims description 6
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
LPVPNRSVMLNXGQ-UHFFFAOYSA-N 1-(azepan-1-yl)-2,2-dichloroethanone Chemical compound ClC(Cl)C(=O)N1CCCCCC1 LPVPNRSVMLNXGQ-UHFFFAOYSA-N 0.000 claims description 4
QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
238000001704 evaporation Methods 0.000 claims description 4
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000004009 herbicide Substances 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
VATNSVZJQOBOIF-UHFFFAOYSA-N 2h-triazin-1-yl carbamate Chemical compound NC(=O)ON1NN=CC=C1 VATNSVZJQOBOIF-UHFFFAOYSA-N 0.000 claims description 2
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims 2
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
238000011282 treatment Methods 0.000 description 40
241000196324 Embryophyta Species 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
239000000843 powder Substances 0.000 description 28
240000008042 Zea mays Species 0.000 description 25
235000002017 Zea mays subsp mays Nutrition 0.000 description 24
239000002689 soil Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 21
RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 17
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 16
235000005822 corn Nutrition 0.000 description 16
238000009331 sowing Methods 0.000 description 15
239000004546 suspension concentrate Substances 0.000 description 15
238000012360 testing method Methods 0.000 description 15
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 14
235000003222 Helianthus annuus Nutrition 0.000 description 13
244000062793 Sorghum vulgare Species 0.000 description 13
239000002270 dispersing agent Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
241000208818 Helianthus Species 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
239000000047 product Substances 0.000 description 12
239000004094 surface-active agent Substances 0.000 description 11
235000011684 Sorghum saccharatum Nutrition 0.000 description 10
JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
229940100389 Sulfonylurea Drugs 0.000 description 8
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 8
235000009973 maize Nutrition 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
231100000674 Phytotoxicity Toxicity 0.000 description 7
229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
241000209140 Triticum Species 0.000 description 7
235000021307 Triticum Nutrition 0.000 description 7
239000002585 base Substances 0.000 description 7
244000038559 crop plants Species 0.000 description 7
239000007788 liquid Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
238000011161 development Methods 0.000 description 6
230000018109 developmental process Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 6
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
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KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
238000005507 spraying Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000230 xanthan gum Substances 0.000 description 5
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ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229920001732 Lignosulfonate Polymers 0.000 description 4
235000019738 Limestone Nutrition 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
230000006378 damage Effects 0.000 description 4
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
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238000011049 filling Methods 0.000 description 4
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239000006028 limestone Substances 0.000 description 4
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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239000002244 precipitate Substances 0.000 description 4
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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230000015572 biosynthetic process Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
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UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000005469 granulation Methods 0.000 description 3
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JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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125000001931 aliphatic group Chemical group 0.000 description 2
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000004744 fabric Substances 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
238000000227 grinding Methods 0.000 description 2
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238000000265 homogenisation Methods 0.000 description 2
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229910052740 iodine Inorganic materials 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
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TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
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239000012860 organic pigment Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
229910001562 pearlite Inorganic materials 0.000 description 1
238000005453 pelletization Methods 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
230000002688 persistence Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
DTQFYYLUCKXRJO-UHFFFAOYSA-N phenyl N-(4,6-dimethylpyrimidin-2-yl)-N-(ethoxymethyl)carbamate Chemical compound C1(=CC=CC=C1)OC(N(COCC)C1=NC(=CC(=N1)C)C)=O DTQFYYLUCKXRJO-UHFFFAOYSA-N 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
150000003021 phthalic acid derivatives Chemical class 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
238000003976 plant breeding Methods 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001522 polyglycol ester Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000344 soap Substances 0.000 description 1
HYOJDTOWSCGXBK-UHFFFAOYSA-N sodium;(2-chlorophenyl)sulfonylazanide Chemical compound [Na+].[NH-]S(=O)(=O)C1=CC=CC=C1Cl HYOJDTOWSCGXBK-UHFFFAOYSA-N 0.000 description 1
IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical class OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
238000009333 weeding Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

LU87884A 1990-01-31 1991-01-31 Herbizid wirksame harnstoff-derivate und verfahren zur herstellung derselben LU87884A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU90600A HU206024B (en)	1990-01-31	1990-01-31	Herbicidal compositions comprising substituted sulfonylurea derivatives and optionally antidote, as well as process for producing the active ingredients
HU60090		1990-01-31

Publications (1)

Publication Number	Publication Date
LU87884A1 true LU87884A1 (de)	1991-07-22

Family

ID=10950375

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87884A LU87884A1 (de)	1990-01-31	1991-01-31	Herbizid wirksame harnstoff-derivate und verfahren zur herstellung derselben

Country Status (29)

Country	Link
JP (1)	JPH069577A (fr)
KR (1)	KR950013855B1 (fr)
CN (1)	CN1053786A (fr)
AU (1)	AU638533B2 (fr)
BE (1)	BE1005348A3 (fr)
BR (1)	BR9100399A (fr)
CA (1)	CA2035319A1 (fr)
CS (1)	CS18891A2 (fr)
DE (1)	DE4102905A1 (fr)
DK (1)	DK16091A (fr)
ES (1)	ES2033200B1 (fr)
FI (1)	FI910456A7 (fr)
FR (1)	FR2658193A1 (fr)
GB (1)	GB2241699A (fr)
GR (1)	GR910100041A (fr)
HU (1)	HU206024B (fr)
IE (1)	IE910321A1 (fr)
IL (1)	IL97342A0 (fr)
IN (1)	IN171736B (fr)
IT (1)	IT1245018B (fr)
LU (1)	LU87884A1 (fr)
NL (1)	NL9100166A (fr)
NO (1)	NO910327L (fr)
NZ (1)	NZ236977A (fr)
PL (2)	PL288905A1 (fr)
PT (1)	PT96606A (fr)
SE (1)	SE9100289L (fr)
YU (1)	YU36391A (fr)
ZA (1)	ZA91583B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4121185B2 (ja)	1998-06-12	2008-07-23	新電元工業株式会社	電子回路装置
DE10218704B4 (de) *	2002-04-26	2006-11-30	Bayer Cropscience Gmbh	Halosulfonylbenzoesäurehalogenide, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung von substituierten Phenylsulfonylharnstoffen

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4371391A (en) *	1980-09-15	1983-02-01	E. I. Du Pont De Nemours And Company	Herbicidal sulfonamides
US4343649A (en) *	1980-11-17	1982-08-10	E. I. Du Pont De Nemours And Company	Herbicide antidotes
US4545811A (en) *	1981-08-06	1985-10-08	Ciba-Geigy Corporation	N-Phenylsulfonyl-N'-triazinyl-ureas
US4579584A (en) *	1981-10-13	1986-04-01	Ciba-Geigy Corporation	N-phenylsulfonyl-N'-triazinylureas
MA19680A1 (fr) *	1982-01-11	1983-10-01	Novartis Ag	N- arylsulfonyl - n' - pyrimidinylurees.
JPS58126872A (ja) *	1982-01-22	1983-07-28	Nippon Tokushu Noyaku Seizo Kk	置換フエニルスルホニルウレア誘導体、その製法及び除草剤
EP0098569A3 (fr) *	1982-07-08	1984-12-19	Hoechst Aktiengesellschaft	Sulfonylurées substituées par un hétérocycle, procédé pour leur préparation et leur utilisation dans l'agriculture
BR8304878A (pt) *	1982-09-10	1984-04-24	Du Pont	Composto e processo para sua preparacao:composicao adequada e processo para controlar o crescimento de vegetacao indesejada
DE3481031D1 (de) *	1983-04-12	1990-02-22	Ciba Geigy Ag	Herbizides mittel.
EP0147365A3 (fr) *	1983-11-03	1985-10-09	Ciba-Geigy Ag	Agent herbicide
US4685961A (en) *	1984-02-14	1987-08-11	Ciba-Geigy Corporation	Herbicidal sulfonylureas
DE3420769A1 (de) *	1984-06-04	1985-12-05	Bayer Ag, 5090 Leverkusen	Substituierte phenylsulfonylharnstoffe
US4645527A (en) *	1984-12-14	1987-02-24	E. I. Du Pont De Nemours And Company	Herbicidal antidotes
EP0190105A3 (fr) *	1985-01-31	1988-10-26	Ciba-Geigy Ag	Agent herbicide
HU201445B (en) *	1987-05-28	1990-11-28	Eszakmagyar Vegyimuevek	Herbicide composition containing sulfonyl-urea derivative as active component and glycinamide derivative as antidotum

1990
- 1990-01-31 HU HU90600A patent/HU206024B/hu not_active IP Right Cessation
1991
- 1991-01-25 ZA ZA91583A patent/ZA91583B/xx unknown
- 1991-01-28 CS CS91188A patent/CS18891A2/cs unknown
- 1991-01-28 YU YU36391A patent/YU36391A/sh unknown
- 1991-01-29 NO NO91910327A patent/NO910327L/no unknown
- 1991-01-29 GB GB9101825A patent/GB2241699A/en not_active Withdrawn
- 1991-01-29 GR GR910100041A patent/GR910100041A/el unknown
- 1991-01-30 PT PT96606A patent/PT96606A/pt not_active Application Discontinuation
- 1991-01-30 SE SE9100289A patent/SE9100289L/xx not_active Application Discontinuation
- 1991-01-30 BR BR919100399A patent/BR9100399A/pt unknown
- 1991-01-30 IT ITTO910059A patent/IT1245018B/it active IP Right Grant
- 1991-01-30 IE IE032191A patent/IE910321A1/en unknown
- 1991-01-30 AU AU70082/91A patent/AU638533B2/en not_active Ceased
- 1991-01-30 BE BE9100088A patent/BE1005348A3/fr not_active IP Right Cessation
- 1991-01-30 CA CA002035319A patent/CA2035319A1/fr not_active Abandoned
- 1991-01-30 DK DK016091A patent/DK16091A/da not_active Application Discontinuation
- 1991-01-31 IN IN66/MAS/91A patent/IN171736B/en unknown
- 1991-01-31 LU LU87884A patent/LU87884A1/de unknown
- 1991-01-31 NL NL9100166A patent/NL9100166A/nl unknown
- 1991-01-31 DE DE4102905A patent/DE4102905A1/de not_active Withdrawn
- 1991-01-31 CN CN91100563A patent/CN1053786A/zh active Pending
- 1991-01-31 FR FR9101082A patent/FR2658193A1/fr active Pending
- 1991-01-31 PL PL91288905A patent/PL288905A1/xx unknown
- 1991-01-31 NZ NZ236977A patent/NZ236977A/en unknown
- 1991-01-31 FI FI910456A patent/FI910456A7/fi not_active Application Discontinuation
- 1991-01-31 PL PL91293799A patent/PL293799A1/xx unknown
- 1991-01-31 ES ES9100250A patent/ES2033200B1/es not_active Expired - Fee Related
- 1991-01-31 JP JP3098310A patent/JPH069577A/ja active Pending
- 1991-01-31 KR KR1019910001821A patent/KR950013855B1/ko not_active Expired - Lifetime
- 1991-02-22 IL IL9197342A patent/IL97342A0/xx unknown

Also Published As

Publication number	Publication date
FR2658193A1 (fr)	1991-08-16
AU638533B2 (en)	1993-07-01
BR9100399A (pt)	1991-10-22
FI910456A0 (fi)	1991-01-31
NL9100166A (nl)	1991-08-16
PT96606A (pt)	1991-10-15
CN1053786A (zh)	1991-08-14
YU36391A (sh)	1994-01-20
DK16091D0 (da)	1991-01-30
ES2033200B1 (es)	1994-04-01
NZ236977A (en)	1992-11-25
PL293799A1 (en)	1993-02-22
IE910321A1 (en)	1991-07-31
CS18891A2 (en)	1991-10-15
IT1245018B (it)	1994-09-13
DK16091A (da)	1991-08-01
IN171736B (fr)	1992-12-26
BE1005348A3 (fr)	1993-07-06
KR910014358A (ko)	1991-08-31
ES2033200A1 (es)	1993-03-01
ITTO910059A1 (it)	1992-07-30
NO910327L (no)	1991-08-01
DE4102905A1 (de)	1991-08-29
ITTO910059A0 (it)	1991-01-30
NO910327D0 (no)	1991-01-29
PL288905A1 (en)	1992-08-10
HU900600D0 (en)	1990-04-28
HUT56239A (en)	1991-08-28
FI910456A7 (fi)	1991-08-01
SE9100289L (sv)	1991-09-04
SE9100289D0 (sv)	1991-01-30
KR950013855B1 (ko)	1995-11-17
JPH069577A (ja)	1994-01-18
GB9101825D0 (en)	1991-03-13
IL97342A0 (en)	1992-05-25
GR910100041A (el)	1992-06-25
HU206024B (en)	1992-08-28
AU7008291A (en)	1991-08-01
CA2035319A1 (fr)	1991-08-01
GB2241699A (en)	1991-09-11
ZA91583B (en)	1991-10-30

Publication	Publication Date	Title
EP0116518B1 (fr)	1987-10-28	Urées N-phénylsulfonyl-N'-pyrimidinyl- et -triazinyl
EP0120814B1 (fr)	1988-07-27	Urées N-phénylsulfonyl-N'-pyrimidinyl- et -triazinyl
EP0099339B1 (fr)	1987-01-07	N-Phénylsulfonyl-N'-pyrimidinyl- et -triazinylurées condensées
EP0084020B1 (fr)	1987-09-16	Urées N-arylsulfonyle-N'-pyrimidinyle
EP0342569B1 (fr)	1994-06-22	2-Alkoxyphénoxysulfonylurées hétérocycliques et leur utilisation comme herbicides ou comme régulateurs de croissance des plantes
EP0044809A1 (fr)	1982-01-27	N-(2-substitué phénylsulfonyl)-N'-triazinyl urées
EP0072347A1 (fr)	1983-02-16	N-Phénylsulfonyl-N'-pyrimidinyl- et -triazinyl-urées
EP0126711A1 (fr)	1984-11-28	Dérivés de pyrimidine actifs comme herbicides et régulateurs de croissance des plantes, leur préparation et leur usage
EP0128116A1 (fr)	1984-12-12	N-Phénylsulfonyl-N'-pyrimidinyl- et -triazinyl urées condensé
EP0353641B1 (fr)	1994-12-07	Sulfonylurées substituées avec des hétérocycles, procédé pour leur préparation et leur utilisation comme herbicides et régulateurs de croissance des plantes
EP0149974A2 (fr)	1985-07-31	Agents pour protéger les plantes cultivées contre l'effet phytotoxique d'herbicides
EP0336354B1 (fr)	1994-11-02	Composés alkyl- et alcénylsulfonylurées hétérocycliquement substitués, procédés pour leur préparation et leur application comme herbicides ou régulateurs de croissance de végétaux
EP0147365A2 (fr)	1985-07-03	Agent herbicide
DD231716A5 (de)	1986-01-08	Herbizide mittel
EP0122231B1 (fr)	1990-01-17	Agent herbicide
EP0058639B1 (fr)	1985-08-14	Esters de l'acide 2-(4-(6-halogène-quinoxalinyl-2-oxy)-phénoxy)-propionique, leurs procédés de préparation et leur application comme herbicides et régulateurs de la croissance de plantes
LU87884A1 (de)	1991-07-22	Herbizid wirksame harnstoff-derivate und verfahren zur herstellung derselben
EP0303114B1 (fr)	1994-08-24	Phénylesters d'acide sulfamique hétérocycliquement substitués, procédé pour leur préparation et leur utilisation comme herbicides et régulateurs de croissance des plantes
DE3324800A1 (de)	1985-01-17	Neue heterocyclisch substituierte sulfonylharnstoffe
EP0409114A1 (fr)	1991-01-23	Sulfonylurées à groupement hétérocycliques, leur procédé de préparation et leur application comme herbicides ou régulateurs de croissance des végétaux
EP0126710A1 (fr)	1984-11-28	Moyen pour protéger les plantes cultivées contre l'effet phytotoxique des herbicides
EP0388771B1 (fr)	1995-06-28	Phénoxysulfonylurées à base d'esters alkyl d'acide salicyclique, procédés pour leur préparation et leur utilisation comme herbicides et régulateurs de croissance des plantes
CN112778315A (zh)	2021-05-11	烟嘧磺酰胺化合物、除草组合物、制备方法、应用
DE3842177A1 (de)	1990-06-21	Substituierte sulfonylharnstoffe
EP0151554A1 (fr)	1985-08-14	Dérivés de phénylsulfonamide