HU194685B - Selective herbicide comprising chloracetanilide and thiolcarbamate derivatives as herbicidal active substance and dioxolane derivative as antidote - Google Patents
Selective herbicide comprising chloracetanilide and thiolcarbamate derivatives as herbicidal active substance and dioxolane derivative as antidote Download PDFInfo
- Publication number
- HU194685B HU194685B HU387984A HU387984A HU194685B HU 194685 B HU194685 B HU 194685B HU 387984 A HU387984 A HU 387984A HU 387984 A HU387984 A HU 387984A HU 194685 B HU194685 B HU 194685B
- Authority
- HU
- Hungary
- Prior art keywords
- herbicidal
- herbicides
- antidote
- herbicide
- eptc
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 62
- 230000002363 herbicidal effect Effects 0.000 title claims description 58
- 239000000729 antidote Substances 0.000 title description 35
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 title description 11
- 150000004862 dioxolanes Chemical class 0.000 title description 3
- 239000013543 active substance Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 38
- OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims description 32
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical group ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 claims description 12
- 239000008096 xylene Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000008061 acetanilides Chemical class 0.000 claims 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 24
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 22
- 240000008042 Zea mays Species 0.000 description 22
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 22
- 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 description 21
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 21
- 239000002689 soil Substances 0.000 description 21
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 20
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 16
- 229940075522 antidotes Drugs 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 235000009973 maize Nutrition 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 14
- 230000000885 phytotoxic effect Effects 0.000 description 12
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 208000024891 symptom Diseases 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 7
- 241000219318 Amaranthus Species 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 239000000084 colloidal system Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- -1 dichloroacetyl Chemical group 0.000 description 5
- 238000009331 sowing Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000209510 Liliopsida Species 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 244000237956 Amaranthus retroflexus Species 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- ZKZMHCFSSXVOHD-UHFFFAOYSA-N [2-[4-[4-(dibutylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]-2-oxoethyl] pentanoate Chemical compound O1C(C)C(O)C(N(CCCC)CCCC)CC1OC1C2=C(O)C(C(=O)C3=C(OC)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(=O)COC(=O)CCCC)C1 ZKZMHCFSSXVOHD-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003864 humus Substances 0.000 description 3
- 239000002563 ionic surfactant Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000272814 Anser sp. Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- NLYNUTMZTCLNOO-UHFFFAOYSA-N Chlorbromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C(Cl)=C1 NLYNUTMZTCLNOO-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 244000115721 Pennisetum typhoides Species 0.000 description 2
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 2
- 241000719029 Polla Species 0.000 description 2
- 235000008515 Setaria glauca Nutrition 0.000 description 2
- 240000003461 Setaria viridis Species 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- PGUJGCSCVAACHH-UHFFFAOYSA-N n-(2-hydroxyethyl)naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)NCCO)=CC=CC2=C1 PGUJGCSCVAACHH-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- CRXGWGIJJCBJLW-UHFFFAOYSA-N n-propylnaphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)NCCC)=CC=CC2=C1 CRXGWGIJJCBJLW-UHFFFAOYSA-N 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical compound CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 description 1
- JBCHWGTZAAZJKG-UHFFFAOYSA-N 2-methyl-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(C)C(=O)C2=C1 JBCHWGTZAAZJKG-UHFFFAOYSA-N 0.000 description 1
- 241000561747 Amaranthus albus Species 0.000 description 1
- 241001666377 Apera Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000008697 Cannabis sativa Nutrition 0.000 description 1
- 241000058192 Chenopodiastrum hybridum Species 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 240000001579 Cirsium arvense Species 0.000 description 1
- 235000005918 Cirsium arvense Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 244000307700 Fragaria vesca Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241001075721 Hibiscus trionum Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 description 1
- 244000237786 Lathyrus tuberosus Species 0.000 description 1
- 235000007252 Lathyrus tuberosus Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241000221024 Mercurialis Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 240000008114 Panicum miliaceum Species 0.000 description 1
- 235000007199 Panicum miliaceum Nutrition 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- 240000006928 Persicaria lapathifolia Species 0.000 description 1
- XPFRXWCVYUEORT-UHFFFAOYSA-N Phenacemide Chemical compound NC(=O)NC(=O)CC1=CC=CC=C1 XPFRXWCVYUEORT-UHFFFAOYSA-N 0.000 description 1
- 241001167724 Reseda lutea Species 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 241000573562 Stachys pubescens Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000007438 Viola pedata Species 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 108010047623 iridine Proteins 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000009343 monoculture Methods 0.000 description 1
- SZOIQCLRXFNYCW-UHFFFAOYSA-N n,n-diethylnaphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N(CC)CC)=CC=CC2=C1 SZOIQCLRXFNYCW-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 229960003396 phenacemide Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
Landscapes
- 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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU387984A HU194685B (en) | 1984-10-17 | 1984-10-17 | Selective herbicide comprising chloracetanilide and thiolcarbamate derivatives as herbicidal active substance and dioxolane derivative as antidote |
| PCT/HU1985/000059 WO1986002237A1 (en) | 1984-10-17 | 1985-10-08 | Herbicidal compositions for killing monocotyledonous and dicotyledonous weeds in maize |
| EP85905099A EP0198870B1 (en) | 1984-10-17 | 1985-10-08 | Herbicidal compositions for killing monocotyledonous and dicotyledonous weeds in maize |
| BR8506994A BR8506994A (pt) | 1984-10-17 | 1985-10-08 | Composicoes herbicidas para a destruicao de ervas daninhas monocotiledoneas e dicotiledoneas no milho |
| AT85905099T ATE53925T1 (de) | 1984-10-17 | 1985-10-08 | Unkrautvertilgungszusammensetzungen zum vernichten von monokotylen und dikotylen unkraeutern in mais. |
| DE8585905099T DE3578305D1 (de) | 1984-10-17 | 1985-10-08 | Unkrautvertilgungszusammensetzungen zum vernichten von monokotylen und dikotylen unkraeutern in mais. |
| GR852508A GR852508B (en, 2012) | 1984-10-17 | 1985-10-16 | |
| CN 85108224 CN1008506B (zh) | 1984-10-17 | 1985-10-16 | 使玉米田中单子叶和双子叶杂草枯萎的除草剂组合物 |
| ES547977A ES8700013A1 (es) | 1984-10-17 | 1985-10-17 | Procedimiento de preparacion de una composicion herbicida para la destruccion de hierbajos monocotiledoneos y dicoti- ledoneos en el maiz |
| CS857399A CS266572B2 (en) | 1984-10-17 | 1985-10-17 | Selective herbicide with antidote content |
| BG075387A BG48803A3 (en) | 1984-10-17 | 1986-06-17 | Herbicide means |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU387984A HU194685B (en) | 1984-10-17 | 1984-10-17 | Selective herbicide comprising chloracetanilide and thiolcarbamate derivatives as herbicidal active substance and dioxolane derivative as antidote |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT39566A HUT39566A (en) | 1986-10-29 |
| HU194685B true HU194685B (en) | 1988-03-28 |
Family
ID=10965893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU387984A HU194685B (en) | 1984-10-17 | 1984-10-17 | Selective herbicide comprising chloracetanilide and thiolcarbamate derivatives as herbicidal active substance and dioxolane derivative as antidote |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0198870B1 (en, 2012) |
| CN (1) | CN1008506B (en, 2012) |
| BG (1) | BG48803A3 (en, 2012) |
| BR (1) | BR8506994A (en, 2012) |
| CS (1) | CS266572B2 (en, 2012) |
| DE (1) | DE3578305D1 (en, 2012) |
| ES (1) | ES8700013A1 (en, 2012) |
| GR (1) | GR852508B (en, 2012) |
| HU (1) | HU194685B (en, 2012) |
| WO (1) | WO1986002237A1 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4664699A (en) * | 1985-02-07 | 1987-05-12 | Stauffer Chemical Company | Method of improving residual herbicidal activity and compositions |
| US5527762A (en) * | 1990-12-12 | 1996-06-18 | Zeneca Limited | Antidoting herbicidal 3-isoxazolidinone compounds |
| US5395816A (en) * | 1990-12-12 | 1995-03-07 | Imperial Chemical Industries Plc | Antidoting herbicidal 3-ixoxazolidinone compounds |
| CN100378208C (zh) * | 2006-03-03 | 2008-04-02 | 中国科学院长春应用化学研究所 | 一种水煤浆 |
| CN100447222C (zh) * | 2006-09-21 | 2008-12-31 | 太原理工大学 | 一种煤沥青水浆及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL282741A (en, 2012) * | 1961-08-31 | |||
| US4415353A (en) * | 1971-04-16 | 1983-11-15 | Stauffer Chemical Company | Herbicide compositions |
| GR71993B (en, 2012) * | 1980-11-19 | 1983-08-26 | Stavffer Chemical Company |
-
1984
- 1984-10-17 HU HU387984A patent/HU194685B/hu not_active IP Right Cessation
-
1985
- 1985-10-08 WO PCT/HU1985/000059 patent/WO1986002237A1/en active IP Right Grant
- 1985-10-08 BR BR8506994A patent/BR8506994A/pt unknown
- 1985-10-08 DE DE8585905099T patent/DE3578305D1/de not_active Expired - Fee Related
- 1985-10-08 EP EP85905099A patent/EP0198870B1/en not_active Expired - Lifetime
- 1985-10-16 GR GR852508A patent/GR852508B/el unknown
- 1985-10-16 CN CN 85108224 patent/CN1008506B/zh not_active Expired
- 1985-10-17 CS CS857399A patent/CS266572B2/cs unknown
- 1985-10-17 ES ES547977A patent/ES8700013A1/es not_active Expired
-
1986
- 1986-06-17 BG BG075387A patent/BG48803A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR852508B (en, 2012) | 1986-02-18 |
| BG48803A3 (en) | 1991-05-15 |
| CN85108224A (zh) | 1986-07-30 |
| DE3578305D1 (de) | 1990-07-26 |
| HUT39566A (en) | 1986-10-29 |
| ES8700013A1 (es) | 1986-10-01 |
| ES547977A0 (es) | 1986-10-01 |
| BR8506994A (pt) | 1987-01-06 |
| WO1986002237A1 (en) | 1986-04-24 |
| EP0198870B1 (en) | 1990-06-20 |
| EP0198870A1 (en) | 1986-10-29 |
| CS266572B2 (en) | 1990-01-12 |
| CN1008506B (zh) | 1990-06-27 |
| CS739985A2 (en) | 1989-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: KSZE NOEVENYTERMELESI RENDSZER AGRARFEJLESZTOE KO Owner name: NITROKEMIA 2000 IPARI ES VAGYONKEZELOE RT., HU |
|
| HMM4 | Cancellation of final prot. due to non-payment of fee |