CS211368B2 - Means with herbicide,growth regulating,fungicide effect - Google Patents
Means with herbicide,growth regulating,fungicide effect Download PDFInfo
- Publication number
- CS211368B2 CS211368B2 CS801526A CS152680A CS211368B2 CS 211368 B2 CS211368 B2 CS 211368B2 CS 801526 A CS801526 A CS 801526A CS 152680 A CS152680 A CS 152680A CS 211368 B2 CS211368 B2 CS 211368B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- thiadiazole
- cyclohexylmethyl
- carboxamidine
- melting point
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 8
- 230000002363 herbicidal effect Effects 0.000 title claims description 4
- 239000004009 herbicide Substances 0.000 title abstract description 4
- 239000000417 fungicide Substances 0.000 title abstract 2
- 230000000694 effects Effects 0.000 title description 21
- 230000012010 growth Effects 0.000 title description 3
- 230000001105 regulatory effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 5
- BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 claims abstract description 3
- -1 chloro, methylamino- Chemical class 0.000 claims description 117
- 239000000203 mixture Substances 0.000 claims description 18
- 239000013543 active substance Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 abstract description 3
- 238000002844 melting Methods 0.000 description 60
- 230000008018 melting Effects 0.000 description 60
- 241000196324 Embryophyta Species 0.000 description 35
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 20
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000011282 treatment Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000005507 spraying Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- MUXLOKHOMNBXNN-UHFFFAOYSA-N 2-(cyclohexylmethyl)-4-methyl-3H-thiadiazole-5-carboximidamide Chemical compound C1(CCCCC1)CN1SC(=C(N1)C)C(=N)N MUXLOKHOMNBXNN-UHFFFAOYSA-N 0.000 description 6
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000722093 Tilletia caries Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
- PDMMAQZSMSZZBD-UHFFFAOYSA-N 4-methylthiadiazole-5-carbothioic s-acid Chemical compound CC=1N=NSC=1C(S)=O PDMMAQZSMSZZBD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000002024 Gossypium herbaceum Species 0.000 description 3
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000228454 Pyrenophora graminea Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- CPPCRKJNHYHEQT-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NCC2CCCCC2)=C1C CPPCRKJNHYHEQT-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000035613 defoliation Effects 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- AGCXVZBIFSUPNI-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-methylthiadiazole-5-carbothioamide Chemical compound N1=NSC(C(=S)NCC2CCCCC2)=C1C AGCXVZBIFSUPNI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000021749 root development Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- IWHLPMBLJZJCJK-UHFFFAOYSA-N 1-cyclohexyl-n-methylmethanamine Chemical compound CNCC1CCCCC1 IWHLPMBLJZJCJK-UHFFFAOYSA-N 0.000 description 1
- FWOSNOGNGGKTRW-UHFFFAOYSA-N 2-(cyclohexylmethyl)-4-methyl-N'-(3-methylbutan-2-yl)-3H-thiadiazole-5-carboximidamide Chemical compound C1(CCCCC1)CN1SC(=C(N1)C)C(=N)NC(C(C)C)C FWOSNOGNGGKTRW-UHFFFAOYSA-N 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- GZDFOOAFMQSYOV-UHFFFAOYSA-N 3-(cyclohexylmethyl)-1,8-dimethyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)C=2NC(C)=NC=2N1CC1CCCCC1 GZDFOOAFMQSYOV-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- JYDYHSHPBDZRPU-UHFFFAOYSA-N 3-methylcyclohexan-1-amine Chemical compound CC1CCCC(N)C1 JYDYHSHPBDZRPU-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 description 1
- 241000743339 Agrostis Species 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- GMIQJCUFNDLRHQ-UHFFFAOYSA-N CCC(C)[S+]1N=NC(C)=C1C(N)=N Chemical compound CCC(C)[S+]1N=NC(C)=C1C(N)=N GMIQJCUFNDLRHQ-UHFFFAOYSA-N 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 241000723343 Cichorium Species 0.000 description 1
- 241000207892 Convolvulus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 241000209210 Dactylis Species 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000919496 Erysimum Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 241001316290 Gypsophila Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 229940124913 IPOL Drugs 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 241000219823 Medicago Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- RHMYYAKINIFKAZ-UHFFFAOYSA-N N'-(cyclohexylmethyl)-N-ethyl-4-methyl-N-propylthiadiazole-5-carboximidamide Chemical compound C(C)N(C(=NCC1CCCCC1)C1=C(N=NS1)C)CCC RHMYYAKINIFKAZ-UHFFFAOYSA-N 0.000 description 1
- HURSPVGFHOVEMK-UHFFFAOYSA-N N-benzyl-4-methylthiadiazole-5-carbothioamide Chemical compound C(C1=CC=CC=C1)NC(=S)C1=C(N=NS1)C HURSPVGFHOVEMK-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000011096 Papaver Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 241001325197 Phacelia Species 0.000 description 1
- 241000745991 Phalaris Species 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DJIBHHGQPSAZCY-UHFFFAOYSA-N butoxy-bis(butylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCOP(=S)(SCCCC)SCCCC DJIBHHGQPSAZCY-UHFFFAOYSA-N 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- VKYWPQQPXULQAJ-UHFFFAOYSA-N n'-(cyclohexylmethyl)-4-methylthiadiazole-5-carboximidamide Chemical compound N1=NSC(C(N)=NCC2CCCCC2)=C1C VKYWPQQPXULQAJ-UHFFFAOYSA-N 0.000 description 1
- DRTBEARBQVFLTK-UHFFFAOYSA-N n-(cyclooctylmethyl)-4-methylthiadiazole-5-carbothioamide Chemical compound N1=NSC(C(=S)NCC2CCCCCCC2)=C1C DRTBEARBQVFLTK-UHFFFAOYSA-N 0.000 description 1
- ARPGITDZCBRBOU-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-4-methylthiadiazole-5-carbothioamide Chemical compound N1=NSC(C(=S)NCC=2C(=CC=CC=2)F)=C1C ARPGITDZCBRBOU-UHFFFAOYSA-N 0.000 description 1
- QGMIIAHFCVYGLV-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methylthiadiazole-5-carbothioamide Chemical compound N1=NSC(C(=S)NCC=2C=CC(F)=CC=2)=C1C QGMIIAHFCVYGLV-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- SZGOQYAJFJBSQD-UHFFFAOYSA-N thiadiazole-5-carboxamide Chemical compound NC(=O)C1=CN=NS1 SZGOQYAJFJBSQD-UHFFFAOYSA-N 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792909991 DE2909991A1 (de) | 1979-03-12 | 1979-03-12 | 1,2,3-thiadiazol-5-carbonsaeurederivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und wuchsregulatorischer sowie fungizider wirkung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS211368B2 true CS211368B2 (en) | 1982-02-26 |
Family
ID=6065357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS801526A CS211368B2 (en) | 1979-03-12 | 1980-03-05 | Means with herbicide,growth regulating,fungicide effect |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4341551A (de) |
| JP (1) | JPS55124773A (de) |
| AR (1) | AR224396A1 (de) |
| AT (1) | AT365893B (de) |
| AU (1) | AU540117B2 (de) |
| BE (1) | BE882195A (de) |
| BG (1) | BG31466A3 (de) |
| BR (1) | BR8001423A (de) |
| CA (1) | CA1154775A (de) |
| CH (1) | CH645365A5 (de) |
| CS (1) | CS211368B2 (de) |
| DD (1) | DD149772A5 (de) |
| DE (1) | DE2909991A1 (de) |
| DK (1) | DK103880A (de) |
| ES (1) | ES489449A1 (de) |
| FR (1) | FR2451371A1 (de) |
| GB (1) | GB2045757B (de) |
| IE (1) | IE49747B1 (de) |
| IL (1) | IL59543A (de) |
| IT (1) | IT1130268B (de) |
| LU (1) | LU82233A1 (de) |
| NL (1) | NL8001157A (de) |
| PL (1) | PL120382B1 (de) |
| RO (2) | RO82507A (de) |
| ZA (1) | ZA801450B (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261657A (en) * | 1978-08-09 | 1981-04-14 | Reiback Earl M | Optical display device |
| DE3030736A1 (de) | 1980-08-14 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | N-disubstituierte anilinderivate, ihre herstellung, ihre verwendung als mikrobizide und mittel dafuer |
| DE3120804A1 (de) * | 1981-05-25 | 1982-12-16 | Basf Ag, 6700 Ludwigshafen | N-substituierte 2-methylnaphthylamide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von pilzen |
| JPH01199901A (ja) * | 1988-02-03 | 1989-08-11 | Mitsui Petrochem Ind Ltd | 種苗・球根類の貯蔵方法 |
| DE4011172A1 (de) * | 1990-04-06 | 1991-10-10 | Degussa | Verbindungen zur bekaempfung von pflanzenkrankheiten |
| US6166054A (en) * | 1995-03-31 | 2000-12-26 | Nihon Nohyaku Co., Ltd. | Agricultural and horticultural disease controller and a method for controlling the diseases |
| MY113237A (en) * | 1995-03-31 | 2001-12-31 | Nihon Nohyaku Co Ltd | An agricultural and horticultural disease controller and a method for controlling the diseases |
| DE19545638A1 (de) * | 1995-12-07 | 1997-06-12 | Bayer Ag | Verwendung von 1,2,3-Thiadiazolcarbonsäure(thio)estern zur Bekämpfung von Schädlingen |
| DE19545637A1 (de) * | 1995-12-07 | 1997-06-12 | Bayer Ag | 1,2,3-Thiadiazolcarbonsäure(thio)ester |
| AU720199B2 (en) | 1996-09-30 | 2000-05-25 | Nihon Nohyaku Co., Ltd. | Bis-thiadiazole derivatives or salts thereof and agrohorticultural disease controller and method for using the same |
| DE102005060466A1 (de) * | 2005-12-17 | 2007-06-28 | Bayer Cropscience Ag | Carboxamide |
| JP2014088322A (ja) * | 2011-01-12 | 2014-05-15 | Nippon Nohyaku Co Ltd | 植物成長調節剤及びその使用方法 |
| CN103214476B (zh) * | 2013-05-02 | 2016-03-02 | 南开大学 | 一类含4-甲基-1,2,3-噻二唑的甲脒衍生物及其制备方法和用途 |
| WO2018116073A1 (en) | 2016-12-21 | 2018-06-28 | Pi Industries Ltd. | 1, 2, 3-thiadiazole compounds and their use as crop protecting agent |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2728523C2 (de) * | 1977-06-23 | 1986-02-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-Methyl-1,2,3-thiadiazol-5-carbonsäure-(cyclohexylmethyl)-amid, Mittel mit herbizider und wachstumsregulatorischer Wirkung enthaltend diese Verbindung sowie Verfahren zu seiner Herstellung |
| DE2841825A1 (de) * | 1978-09-22 | 1980-04-03 | Schering Ag | Verfahren zur herstellung von 1,2,3- thiadiazol-5-yl-harnstoffen |
-
1979
- 1979-03-12 DE DE19792909991 patent/DE2909991A1/de not_active Withdrawn
-
1980
- 1980-02-26 NL NL8001157A patent/NL8001157A/nl not_active Application Discontinuation
- 1980-03-04 IT IT20333/80A patent/IT1130268B/it active
- 1980-03-05 CS CS801526A patent/CS211368B2/cs unknown
- 1980-03-05 US US06/127,496 patent/US4341551A/en not_active Expired - Lifetime
- 1980-03-06 IL IL59543A patent/IL59543A/xx unknown
- 1980-03-06 CH CH177380A patent/CH645365A5/de not_active IP Right Cessation
- 1980-03-07 DD DD80219527A patent/DD149772A5/de unknown
- 1980-03-10 LU LU82233A patent/LU82233A1/de unknown
- 1980-03-10 PL PL1980222581A patent/PL120382B1/pl unknown
- 1980-03-10 BG BG046920A patent/BG31466A3/xx unknown
- 1980-03-11 AT AT0134380A patent/AT365893B/de not_active IP Right Cessation
- 1980-03-11 BR BR8001423A patent/BR8001423A/pt unknown
- 1980-03-11 DK DK103880A patent/DK103880A/da unknown
- 1980-03-11 CA CA000347428A patent/CA1154775A/en not_active Expired
- 1980-03-12 JP JP3041980A patent/JPS55124773A/ja active Pending
- 1980-03-12 ZA ZA00801450A patent/ZA801450B/xx unknown
- 1980-03-12 FR FR8005521A patent/FR2451371A1/fr active Granted
- 1980-03-12 IE IE499/80A patent/IE49747B1/en unknown
- 1980-03-12 BE BE0/199770A patent/BE882195A/fr not_active IP Right Cessation
- 1980-03-12 GB GB8008348A patent/GB2045757B/en not_active Expired
- 1980-03-12 RO RO80104865A patent/RO82507A/ro unknown
- 1980-03-12 RO RO80100458A patent/RO79386A/ro unknown
- 1980-03-12 ES ES489449A patent/ES489449A1/es not_active Expired
- 1980-03-12 AR AR280279D patent/AR224396A1/es active
- 1980-03-12 AU AU56387/80A patent/AU540117B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BE882195A (fr) | 1980-09-12 |
| IT1130268B (it) | 1986-06-11 |
| BR8001423A (pt) | 1980-11-11 |
| NL8001157A (nl) | 1980-09-16 |
| BG31466A3 (en) | 1982-01-15 |
| CH645365A5 (de) | 1984-09-28 |
| RO82507B (ro) | 1983-08-30 |
| FR2451371A1 (fr) | 1980-10-10 |
| AR224396A1 (es) | 1981-11-30 |
| US4341551A (en) | 1982-07-27 |
| AT365893B (de) | 1982-02-25 |
| ZA801450B (en) | 1980-12-31 |
| AU540117B2 (en) | 1984-11-01 |
| LU82233A1 (de) | 1980-06-06 |
| RO82507A (ro) | 1983-09-26 |
| GB2045757A (en) | 1980-11-05 |
| FR2451371B1 (de) | 1984-05-18 |
| DD149772A5 (de) | 1981-07-29 |
| ATA134380A (de) | 1981-07-15 |
| RO79386A (ro) | 1982-06-25 |
| PL120382B1 (en) | 1982-02-27 |
| AU5638780A (en) | 1980-09-18 |
| GB2045757B (en) | 1983-02-09 |
| IL59543A0 (en) | 1980-06-30 |
| JPS55124773A (en) | 1980-09-26 |
| IL59543A (en) | 1984-03-30 |
| IE800499L (en) | 1980-09-12 |
| DK103880A (da) | 1980-09-13 |
| PL222581A1 (de) | 1980-12-15 |
| IE49747B1 (en) | 1985-12-11 |
| DE2909991A1 (de) | 1980-10-02 |
| CA1154775A (en) | 1983-10-04 |
| IT8020333A0 (it) | 1980-03-04 |
| ES489449A1 (es) | 1980-09-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1204322B1 (de) | Fungizide verbindungen | |
| ES2200816T3 (es) | Derivados de n2-fenil-amidina. | |
| PL110342B1 (en) | Herbicide and controller of growth | |
| WO2001011965A1 (en) | Fungicides | |
| PT1178039E (pt) | Derivados fungicidas de fenil (tio) ureias e de fenil (tio) carbamatos | |
| JPH0143751B2 (de) | ||
| CS211368B2 (en) | Means with herbicide,growth regulating,fungicide effect | |
| NZ199882A (en) | N-heterocyclyl-methyl-amide derivatives and fungicidal and herbicidal compositions | |
| JPS58103371A (ja) | 除草剤用スルホンアミド類 | |
| US4343945A (en) | 5-Benzamido-3-trichloromethyl-1,2,4-thiadiazoles and their use as herbicides, fungicides and insecticides | |
| US4144049A (en) | N-(4-Benzyloxyphenyl)-N-methyl-N-methoxyurea | |
| KR900001910B1 (ko) | 1-디메틸카르바모일-3-치환-5-치환-1h-1,2,4-트리아졸 및 그의 제조방법 | |
| US4501746A (en) | N,N-disubstituted carboxamide derivatives, and fungicidal use thereof | |
| SU965355A3 (ru) | Способ получени производных амидов 1,2,3-тиадиазол-5-карбоновой кислоты (его варианты) | |
| US4911745A (en) | Novel 2-(substituted imino)-1,3,4-dihydrothladiazoles | |
| PL118237B1 (en) | Biocide | |
| JPS63295554A (ja) | N−アリールピロリン−2,5−ジオン | |
| DE3781769T2 (de) | 1-carbamoyl-2-pyrazolin-derivate mit herbizidischer wirkung. | |
| CS244127B2 (en) | Fungicide,growth regulating and bactericidal agent | |
| KR810001152B1 (ko) | 1, 2, 3-티아디아졸-5-카복실산 유도체의 제조방법 | |
| JPH04178362A (ja) | 尿素誘導体およびそれを含有する有害生物防除剤 | |
| JPS60146888A (ja) | チオラン‐2,4‐ジオン‐3‐カルボキシアミド類 | |
| JPH0261459B2 (de) | ||
| HU205904B (en) | Fungicide compositions containing cyclopropane-carboxylic acid derivatives as active components and process for producing the active components | |
| JPH0331706B2 (de) |