BE578356A - - Google Patents
Info
- Publication number
- BE578356A BE578356A BE578356DA BE578356A BE 578356 A BE578356 A BE 578356A BE 578356D A BE578356D A BE 578356DA BE 578356 A BE578356 A BE 578356A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- compound
- herbicidal composition
- industrial product
- composition according
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 36
- 230000002363 herbicidal Effects 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 150000003931 anilides Chemical class 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 claims description 8
- -1 chloro - Chemical class 0.000 claims description 7
- VCBRBUKGTWLJOB-UHFFFAOYSA-N Chloranocryl Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCBRBUKGTWLJOB-UHFFFAOYSA-N 0.000 claims description 5
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical group O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- AAMKOBUANACSLQ-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)NC(C(=CCC)C)=O Chemical compound ClC=1C=C(C=CC1Cl)NC(C(=CCC)C)=O AAMKOBUANACSLQ-UHFFFAOYSA-N 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N Methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
- KHKQLHGXCMYPRB-UHFFFAOYSA-N N-(4-chloro-3-methylphenyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(C)=C1 KHKQLHGXCMYPRB-UHFFFAOYSA-N 0.000 claims description 3
- 239000004563 wettable powder Substances 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- BHGAQZHIWVFABO-UHFFFAOYSA-N CC=1C=C(C=CC1C)NC(C(=CC)C)=O Chemical compound CC=1C=C(C=CC1C)NC(C(=CC)C)=O BHGAQZHIWVFABO-UHFFFAOYSA-N 0.000 claims 1
- NHQXXNQUBYATDQ-UHFFFAOYSA-N CC=1C=C(C=CC1C)NC(C(=CCC)C)=O Chemical compound CC=1C=C(C=CC1C)NC(C(=CCC)C)=O NHQXXNQUBYATDQ-UHFFFAOYSA-N 0.000 claims 1
- GHVVHTBODMHHAF-UHFFFAOYSA-N CC=1C=C(C=CC1Cl)NC(C(=CCC)C)=O Chemical compound CC=1C=C(C=CC1Cl)NC(C(=CCC)C)=O GHVVHTBODMHHAF-UHFFFAOYSA-N 0.000 claims 1
- XNXCPCWMJGQWFF-UHFFFAOYSA-N N-(3-chloro-4-methylphenyl)-2-methylpent-2-enamide Chemical compound CCC=C(C)C(=O)NC1=CC=C(C)C(Cl)=C1 XNXCPCWMJGQWFF-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000006193 liquid solution Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 530
- 241000196324 Embryophyta Species 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 229920000742 Cotton Polymers 0.000 description 9
- 240000006962 Gossypium hirsutum Species 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000004009 herbicide Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 240000002860 Daucus carota Species 0.000 description 5
- 235000002767 Daucus carota Nutrition 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 240000000772 Brassica cretica Species 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 240000005158 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000009973 maize Nutrition 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 230000001473 noxious Effects 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HIHCTGNZNHSZPP-UHFFFAOYSA-N 4-chloro-3-methylaniline Chemical compound CC1=CC(N)=CC=C1Cl HIHCTGNZNHSZPP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N Isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N Methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- RQKFYFNZSHWXAW-UHFFFAOYSA-N Starlicide Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 2
- 240000006802 Vicia sativa Species 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005610 enamide group Chemical group 0.000 description 2
- 230000029578 entry into host Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000001373 (E)-2-methylpent-2-enoic acid Substances 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 1
- KFTHUBZIEMOORC-UHFFFAOYSA-N 2-methylbut-2-enamide Chemical compound CC=C(C)C(N)=O KFTHUBZIEMOORC-UHFFFAOYSA-N 0.000 description 1
- PGTISPYIJZXZSE-UHFFFAOYSA-N 2-methylpent-2-enamide Chemical compound CCC=C(C)C(N)=O PGTISPYIJZXZSE-UHFFFAOYSA-N 0.000 description 1
- JJYWRQLLQAKNAD-UHFFFAOYSA-N 2-methylpent-2-enoic acid Chemical compound CCC=C(C)C(O)=O JJYWRQLLQAKNAD-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 240000001452 Canavalia ensiformis Species 0.000 description 1
- 240000000218 Cannabis sativa Species 0.000 description 1
- PTROIRSGOGPSMB-UHFFFAOYSA-N ClC=1C=C(C=CC1C)NC(C(=C)C)=O Chemical compound ClC=1C=C(C=CC1C)NC(C(=C)C)=O PTROIRSGOGPSMB-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- FXZWPZMCZNJILD-UHFFFAOYSA-N N-[(6-bromopyridin-3-yl)methyl]ethanamine;hydrochloride Chemical compound Cl.CCNCC1=CC=C(Br)N=C1 FXZWPZMCZNJILD-UHFFFAOYSA-N 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N Tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 240000008529 Triticum aestivum Species 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005824 corn Nutrition 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001627 detrimental Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M laurate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- MZDYAVCNKNXCIS-UHFFFAOYSA-N pent-2-enamide Chemical compound CCC=CC(N)=O MZDYAVCNKNXCIS-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 235000021307 wheat Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE578356A true BE578356A (ja) |
Family
ID=190981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE578356D BE578356A (ja) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE578356A (ja) |
-
0
- BE BE578356D patent/BE578356A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2765577A1 (fr) | Nouveaux amides aromatiques, leur procede de preparation et leur application comme pesticides | |
| JPH0124779B2 (ja) | ||
| JPH0324469B2 (ja) | ||
| FR2471979A1 (fr) | Derives du tetrahydrofuranne, leur procede de preparation et leur application comme herbicide | |
| BE578356A (ja) | ||
| EP0034556B1 (fr) | Compositions régulatrices de la croissance des plantes contenant comme matière active des dérivés de l'acide méthylène-2 succinamique et nouveaux dérivés de cet acide utilisables dans ces compositions | |
| FR2594437A1 (fr) | Nouveaux derives du cyano-2 benzimidazole, leur preparation, les compositions les contenant et leur utilisation comme fongicide | |
| FR2761986A1 (fr) | Nouveaux amides aromatiques, leur procede de preparation et leur application comme pesticides | |
| EP0030514B1 (fr) | Dérivés de l'aniline, procédé pour leur préparation et compositions régulatrices de la croissance des plantes les contenant | |
| WO1980000344A1 (fr) | Nouvelle phenyluree substituee herbicide | |
| KR830000743B1 (ko) | 치환페닐 요소의 제조법 | |
| FR2519338A1 (fr) | Nouveaux derives de 3-nitrobenzenesulfonanilide, compositions fongicides les contenant comme ingredients actifs et procede pour lutter contre la hernie du chou les utilisant | |
| EP0249567A2 (fr) | Dérivés propargyloxybenzènes, leur préparation et compositions fongicides les contenant | |
| FR2563220A1 (fr) | Nouveaux derives 1-methylene-carbonyliques de 3-aryloxy-4-phenyl-azet-2 ones et leur application comme substances de croissance des plantes | |
| JPS59106454A (ja) | 新規な尿素誘導体、その製造法および殺虫組成物 | |
| BE577496A (ja) | ||
| FR2499562A1 (fr) | Phenylcarbamoylbenzimidates, leur preparation et leur utilisation | |
| LU83355A1 (fr) | Ethers diphenyliques a activite herbicide | |
| FR2608898A1 (fr) | Associations fongicides a base de cyanobenzimidazole et d'un fongicide systemique | |
| FR2471368A1 (fr) | Procede de production de derives de n-benzylpivalylamide, nouveaux produits ainsi obtenus et leur utilisation comme herbicides | |
| FR2481273A1 (fr) | 4-(4-(anilino)phenoxy)2-pentenoique et derives de cet acide, leur preparation et herbicides selectifs a base de ces substances | |
| BE853355A (fr) | Composes herbicides, compositions herbicides en contenant et leur procede d'utilisation | |
| FR2509580A1 (fr) | 1-phenyl-1,2,3-triazoles utilisables comme anti-appetants et leur preparation | |
| FR2499568A1 (fr) | Nouveaux n-(2-oxo-oxazolidino) -acetamides ayant des proprietes fongicides et compositions les contenant | |
| BE892042A (fr) | Phenylcarbamoylbenzimidates, leur preparation et leur utilisation |