IL97910A - Nematode-killing preparations containing benzaziaziazoles, certain new compounds and their preparation - Google Patents

Nematode-killing preparations containing benzaziaziazoles, certain new compounds and their preparation

Info

Publication number: IL97910A
Authority: IL; Israel
Prior art keywords: formula; compound; compounds; nematodes; active ingredient
Prior art date: 1990-04-23

Application number

IL9791091A

Other languages

English (en)

Hebrew (he)

Other versions

IL97910A0 (en

Original Assignee

Ciba Geigy Ag

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.)

1990-04-23

Filing date

1991-04-22

Publication date

1995-08-31

1991-04-22 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1992-06-21 Publication of IL97910A0 publication Critical patent/IL97910A0/xx

1995-08-31 Publication of IL97910A publication Critical patent/IL97910A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 71
239000000203 mixture Substances 0.000 title claims description 61
238000002360 preparation method Methods 0.000 title abstract description 14
230000001069 nematicidal effect Effects 0.000 title description 13
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title description 10
238000000034 method Methods 0.000 claims abstract description 24
241000244206 Nematoda Species 0.000 claims abstract description 18
229910052736 halogen Chemical group 0.000 claims abstract description 14
150000002367 halogens Chemical group 0.000 claims abstract description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
239000004480 active ingredient Substances 0.000 claims description 22
239000002671 adjuvant Substances 0.000 claims description 12
239000007787 solid Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000004094 surface-active agent Substances 0.000 claims description 9
239000007788 liquid Substances 0.000 claims description 7
AUYJMVMBVRSCMW-UHFFFAOYSA-N 5-nitro-1,2-benzothiazole Chemical compound [O-][N+](=O)C1=CC=C2SN=CC2=C1 AUYJMVMBVRSCMW-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Chemical group 0.000 claims description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000011630 iodine Chemical group 0.000 claims description 5
229910052740 iodine Chemical group 0.000 claims description 5
VSVKOUBCDZYAQY-UHFFFAOYSA-N 7-chloro-1,2-benzothiazole Chemical compound ClC1=CC=CC2=C1SN=C2 VSVKOUBCDZYAQY-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
241001480224 Heterodera Species 0.000 claims description 3
241001143352 Meloidogyne Species 0.000 claims description 3
244000045947 parasite Species 0.000 claims description 2
241000894007 species Species 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 6
239000003795 chemical substances by application Substances 0.000 abstract description 2
239000005645 nematicide Substances 0.000 abstract description 2
239000013543 active substance Substances 0.000 abstract 2
239000000243 solution Substances 0.000 description 21
-1 aromatic radical Chemical class 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
241000196324 Embryophyta Species 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
238000009472 formulation Methods 0.000 description 10
239000002202 Polyethylene glycol Substances 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229920001223 polyethylene glycol Polymers 0.000 description 9
239000005995 Aluminium silicate Substances 0.000 description 8
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
235000012211 aluminium silicate Nutrition 0.000 description 8
239000002585 base Substances 0.000 description 8
239000000969 carrier Substances 0.000 description 8
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 8
239000000725 suspension Substances 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
NEROCZWWNXWPOV-UHFFFAOYSA-N 1,2-benzothiazol-7-amine Chemical compound NC1=CC=CC2=C1SN=C2 NEROCZWWNXWPOV-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241000498254 Heterodera glycines Species 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000002736 nonionic surfactant Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000002689 soil Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000243786 Meloidogyne incognita Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000012954 diazonium Substances 0.000 description 4
235000013601 eggs Nutrition 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
238000005516 engineering process Methods 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
238000002156 mixing Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
150000003568 thioethers Chemical class 0.000 description 4
BZTUCTZFJZJNHZ-UHFFFAOYSA-N 2-benzylsulfanyl-3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1SCC1=CC=CC=C1 BZTUCTZFJZJNHZ-UHFFFAOYSA-N 0.000 description 3
JJSWRWOWWXTUBG-UHFFFAOYSA-N 4-nitro-1,2-benzothiazole Chemical compound [O-][N+](=O)C1=CC=CC2=C1C=NS2 JJSWRWOWWXTUBG-UHFFFAOYSA-N 0.000 description 3
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
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 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000003240 coconut oil Substances 0.000 description 3
235000019864 coconut oil Nutrition 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
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 3
239000008187 granular material Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229920005552 sodium lignosulfonate Polymers 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
LARBSDOBTWXILM-UHFFFAOYSA-N 7-bromo-1,2-benzothiazole Chemical compound BrC1=CC=CC2=C1SN=C2 LARBSDOBTWXILM-UHFFFAOYSA-N 0.000 description 2
BLCKJQHQAZXAOL-UHFFFAOYSA-N 7-fluoro-1,2-benzothiazole Chemical compound FC1=CC=CC2=C1SN=C2 BLCKJQHQAZXAOL-UHFFFAOYSA-N 0.000 description 2
XYFHXKUXMXHTPU-UHFFFAOYSA-N 7-nitro-1,2-benzothiazole Chemical compound [O-][N+](=O)C1=CC=CC2=C1SN=C2 XYFHXKUXMXHTPU-UHFFFAOYSA-N 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000000297 Sandmeyer reaction Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000003093 cationic surfactant Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000007931 coated granule Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
229910052625 palygorskite Inorganic materials 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000004323 potassium nitrate Substances 0.000 description 2
235000010333 potassium nitrate Nutrition 0.000 description 2
239000004576 sand Substances 0.000 description 2
239000000344 soap Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
238000005979 thermal decomposition reaction Methods 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
WIJQCPIRWXSWQG-UHFFFAOYSA-N 1,2-benzothiazol-3-amine Chemical compound C1=CC=C2C(N)=NSC2=C1 WIJQCPIRWXSWQG-UHFFFAOYSA-N 0.000 description 1
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 description 1
JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical group CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
GUJLUJZWVORAKY-UHFFFAOYSA-N 2-benzylsulfanyl-6-chlorobenzaldehyde Chemical compound ClC1=CC=CC(SCC=2C=CC=CC=2)=C1C=O GUJLUJZWVORAKY-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
BCPVKLRBQLRWDQ-UHFFFAOYSA-N 3-chloro-1,2-benzothiazole Chemical class C1=CC=C2C(Cl)=NSC2=C1 BCPVKLRBQLRWDQ-UHFFFAOYSA-N 0.000 description 1
DHLIRMWNYRKKPN-UHFFFAOYSA-N 4-chloro-1,2-benzothiazole Chemical compound ClC1=CC=CC2=C1C=NS2 DHLIRMWNYRKKPN-UHFFFAOYSA-N 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
KDBXNTXKUGUISU-UHFFFAOYSA-N 5-chloro-1,2-benzothiazole Chemical compound ClC1=CC=C2SN=CC2=C1 KDBXNTXKUGUISU-UHFFFAOYSA-N 0.000 description 1
SBTCGVVBXKUUPA-UHFFFAOYSA-N 5-chloro-2-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(Cl)C=C1C=O SBTCGVVBXKUUPA-UHFFFAOYSA-N 0.000 description 1
LOQXWJAZYXSIJE-UHFFFAOYSA-N 6-chloro-1,2-benzothiazole Chemical compound ClC1=CC=C2C=NSC2=C1 LOQXWJAZYXSIJE-UHFFFAOYSA-N 0.000 description 1
IZKNDXNNYCZGOU-UHFFFAOYSA-N 7-iodo-1,2-benzothiazole Chemical compound IC1=CC=CC2=C1SN=C2 IZKNDXNNYCZGOU-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
241000208140 Acer Species 0.000 description 1
241000380490 Anguina Species 0.000 description 1
241000294569 Aphelenchoides Species 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
240000007124 Brassica oleracea Species 0.000 description 1
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000399934 Ditylenchus Species 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
241001442498 Globodera Species 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
241001220360 Longidorus Species 0.000 description 1
241000243785 Meloidogyne javanica Species 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
241000193943 Pratylenchus Species 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
241000201377 Radopholus Species 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
241001220308 Trichodorus Species 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241001267618 Tylenchulus Species 0.000 description 1
241000201423 Xiphinema Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
BCOZLGOHQFNXBI-UHFFFAOYSA-M benzyl-bis(2-chloroethyl)-ethylazanium;bromide Chemical compound [Br-].ClCC[N+](CC)(CCCl)CC1=CC=CC=C1 BCOZLGOHQFNXBI-UHFFFAOYSA-M 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000011449 brick Substances 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
208000031513 cyst Diseases 0.000 description 1
230000037416 cystogenesis Effects 0.000 description 1
239000003599 detergent Substances 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
UAWLRDNECXNKHV-UHFFFAOYSA-N ethane-1,2-diol;2-nonylphenol Chemical compound OCCO.CCCCCCCCCC1=CC=CC=C1O UAWLRDNECXNKHV-UHFFFAOYSA-N 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000005452 ethyl sulfates Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
150000003854 isothiazoles Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000005451 methyl sulfates Chemical class 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
239000003750 molluscacide Substances 0.000 description 1
230000002013 molluscicidal effect Effects 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
150000002888 oleic acid derivatives Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
238000004321 preservation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001737 promoting effect Effects 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
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
235000003441 saturated fatty acids Nutrition 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
229920002545 silicone oil Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
239000003760 tallow Substances 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
150000003512 tertiary amines Chemical class 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
244000045561 useful plants Species 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- 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
- A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Thiazole And Isothizaole Compounds (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Liquid Crystal Substances (AREA)
Dental Preparations (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IL9791091A 1990-04-23 1991-04-22 Nematode-killing preparations containing benzaziaziazoles, certain new compounds and their preparation IL97910A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH135890		1990-04-23
CH25691		1991-01-28

Publications (2)

Publication Number	Publication Date
IL97910A0 IL97910A0 (en)	1992-06-21
IL97910A true IL97910A (en)	1995-08-31

Family

ID=25684048

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9791091A IL97910A (en)	1990-04-23	1991-04-22	Nematode-killing preparations containing benzaziaziazoles, certain new compounds and their preparation

Country Status (18)

Country	Link
US (2)	US5169951A (es)
EP (1)	EP0454621B1 (es)
JP (3)	JP3008035B2 (es)
KR (1)	KR0168442B1 (es)
AT (1)	ATE194604T1 (es)
AU (1)	AU636738B2 (es)
BR (1)	BR9101605A (es)
CA (1)	CA2040889C (es)
DE (1)	DE59109193D1 (es)
DK (1)	DK0454621T3 (es)
ES (1)	ES2148146T3 (es)
GR (1)	GR3033987T3 (es)
IE (1)	IE911334A1 (es)
IL (1)	IL97910A (es)
NZ (1)	NZ237888A (es)
PT (1)	PT97431B (es)
SG (1)	SG47031A1 (es)
TR (1)	TR26713A (es)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0530136B1 (de) *	1991-07-17	1996-02-21	Ciba-Geigy Ag	Nematizide Mittel
TW241263B (es) *	1991-08-22	1995-02-21	Hoechst Roussel Pharma
TW268947B (es) *	1993-09-13	1996-01-21	Ciba Geigy
AU1014300A (en) *	1999-01-19	2000-07-20	American Cyanamid Company	Herbicidal compositions and method of safening herbicides using benzothiazole derivatives
US6281168B1 (en)	1999-01-19	2001-08-28	American Cyanamid Co.	Herbicidal compositions and method of safening herbicides using benzothiazole derivatives
US6353111B1 (en)	1999-12-15	2002-03-05	Hoffmann-La Roche Inc.	Trans olefinic glucokinase activators
BR0309546A (pt) *	2002-04-26	2005-02-15	Hoffmann La Roche	Composto, composição farmacêutica que compreende o mesmo, processo para a sua preparação e utilização e método para tratamento profilático ou terapêutico de diabetes do tipo ii
US7056864B2 (en) *	2002-07-11	2006-06-06	The United States Of America As Represented By The Secretary Of Agriculture	Methods of reducing pests by use of halogen substituted ethanol
MY141521A (en)	2002-12-12	2010-05-14	Hoffmann La Roche	5-substituted-six-membered heteroaromatic glucokinase activators
AU2005251448B2 (en) *	2004-06-07	2011-04-14	Syngenta Participations Ag	Methods of reducing Nematode damage
BRPI0611063A2 (pt) *	2005-06-03	2016-11-16	Basf Ag	misturas pesticidas, uso de uma mistura, métodos para proteger plantas do ataque ou infestação por insetos ou aracnídeos, para controlar insetos ou aracnídeos, e para tratar, controlar, prevenir ou proteger um animal de sangue quente ou um peixe contra infestação ou infecção por parasitas, composição pesticida, e, processo para preparar uma composição.
MX2008016215A (es)	2006-06-22	2009-01-19	Basf Se	Compuestos de malononitrilo.
AR062844A1 (es)	2006-09-14	2008-12-10	Basf Ag	Composicion pesticida
UA110598C2 (uk)	2006-11-10	2016-01-25	Басф Се	Спосіб одержання кристалічної модифікації фіпронілу
HRP20110641T4 (hr)	2006-11-10	2015-05-22	Basf Se	Kristalna modifikacija fipronila
EP2083628A1 (en)	2006-11-10	2009-08-05	Basf Se	Crystalline modification of fipronil
AU2007316639B2 (en)	2006-11-10	2012-12-20	Basf Se	Crystalline modification of fipronil
WO2008064990A2 (en) *	2006-11-30	2008-06-05	Basf Se	Agrochemical formulations comprising l-vinyl-2 -pyrrolidinone co-polymers
WO2008065050A1 (en) *	2006-11-30	2008-06-05	Basf Se	Agrochemical formulations comprising co-polymers based on diisocyanates
ATE468748T1 (de) *	2006-11-30	2010-06-15	Basf Se	Agrarchemikalienformulierungen, die n-vinylamid- copolymere enthalten
EP2258177A3 (en)	2006-12-15	2011-11-09	Rohm and Haas Company	Mixtures comprising 1-methylcyclopropene
US8211828B2 (en)	2007-01-19	2012-07-03	Basf Se	Fungicidal mixtures of 1-methylpyrazol-4-ylcarboxanilides and azolopyrimidinylamines
ES2383101T3 (es)	2007-01-26	2012-06-18	Basf Se	Compuestos de 3-amino-1,2-bencisotiazol para combatir plagas animales II
EP1952690A3 (en)	2007-01-31	2009-04-22	Basf Se	Pesticidal mixtures based on triazolopyrimidines and insecticides
CL2008000357A1 (es)	2007-02-06	2009-09-11	Basf Se	Agente que contiene al menos un antagonista de gaba, tal como fipronilo, al menos un fungicida de azol, tal como triconazol y al menos una giberelina; y su uso para mejorar la germinacion y/o la emergencia y/o vitalidad de las plantas.
EP2114163B1 (en)	2007-04-12	2017-05-10	Basf Se	Pesticidal mixtures comprising a cyanosulfoximine compound
CA2682294A1 (en)	2007-04-23	2008-10-30	Basf Se	Plant productivity enhancement by combining chemical agents with transgenic modifications
CL2008002420A1 (es)	2007-08-16	2009-10-23	Basf Se	Uso de una composicion que comprende a) un ingrediente activo seleccionado de piraclostrobina; b) un sulfato de eter poliarilfenol polialcoxi; y c) un co-polimero basado en esteres metaacrilicos para el tratamiento de semillas y composicion para el tratamiento de semillas.
HUE048086T2 (hu)	2007-09-20	2020-05-28	Bayer Cropscience Lp	Fungicid törzset és legalább egy további fungicidet tartalmazó kombinációk
US20100307101A1 (en) *	2007-12-21	2010-12-09	Basf Se	Insecticide-equipped particles made of expandable polystyrene and insecticide-equipped molded parts which can be obtained therefrom
WO2009080464A2 (en) *	2007-12-21	2009-07-02	Basf Se	Process for the production of insecticide-modified bead material composed of expandable polystyrene and insecticide-modified moldings obtainable therefrom
JP2011510033A (ja)	2008-01-25	2011-03-31	シンジェンタパーティシペーションズアクチェンゲゼルシャフト	化合物
JP2012506403A (ja) *	2008-10-22	2012-03-15	ビーエーエスエフソシエタス・ヨーロピア	殺虫剤修飾ｘｐｓプレフォームの製造方法
CA2749223C (en)	2009-01-27	2017-07-04	Basf Se	Method for dressing seeds
WO2010089244A1 (en)	2009-02-03	2010-08-12	Basf Se	Method for dressing seeds
JP2012519662A (ja)	2009-03-04	2012-08-30	ビーエーエスエフソシエタス・ヨーロピア	無脊椎有害生物を駆除するための３−アリールキナゾリン−４−オン化合物
ES2472918T3 (es)	2009-07-06	2014-07-03	Basf Se	Compuestos de piridazina para controlar plagas de invertebrados
JP2013500246A (ja)	2009-07-24	2013-01-07	ビーエーエスエフソシエタス・ヨーロピア	無脊椎動物系害虫防除用ピリジン誘導体化合物
US8343706B2 (en) *	2010-01-25	2013-01-01	International Business Machines Corporation	Fluorine-free fused ring heteroaromatic photoacid generators and resist compositions containing the same
WO2011117286A1 (en)	2010-03-23	2011-09-29	Basf Se	Pyridazine compounds for controlling invertebrate pests
AR100304A1 (es)	2014-02-05	2016-09-28	Basf Corp	Formulación de recubrimiento de semillas
CN105432652A (zh) *	2015-12-14	2016-03-30	济南舜昊生物科技有限公司	一种含有benclothiaz和呋虫胺的杀虫组合物
CN105432624A (zh) *	2015-12-14	2016-03-30	济南舜昊生物科技有限公司	一种含有benclothiaz和溴虫苯甲酰胺的杀虫组合物
CN105284865A (zh) *	2015-12-14	2016-02-03	济南舜昊生物科技有限公司	一种含有benclothiaz和噻虫嗪的杀虫组合物
CN105432640A (zh) *	2015-12-14	2016-03-30	济南舜昊生物科技有限公司	一种含有benclothiaz和联苯肼酯的杀虫组合物
CN105475336A (zh) *	2015-12-14	2016-04-13	济南舜昊生物科技有限公司	一种含有benclothiaz和吡虫啉的杀虫组合物
CN105340922A (zh) *	2015-12-14	2016-02-24	济南舜昊生物科技有限公司	一种含有benclothiaz和阿维菌素的杀虫组合物
CN105340940A (zh) *	2015-12-14	2016-02-24	济南舜昊生物科技有限公司	一种含有benclothiaz和茚虫威的杀虫组合物
CN105340908A (zh) *	2015-12-14	2016-02-24	济南舜昊生物科技有限公司	一种含有benclothiaz和甲氧虫酰肼的杀虫组合物
CN105360139A (zh) *	2015-12-14	2016-03-02	济南舜昊生物科技有限公司	一种含有benclothiaz和氯虫苯甲酰胺的杀虫组合物
CN105340948A (zh) *	2015-12-14	2016-02-24	济南舜昊生物科技有限公司	一种含有benclothiaz和高效氯氟氰菊酯的杀虫组合物
WO2025242701A1 (en)	2024-05-22	2025-11-27	Basf Se	Seed treatment compositions

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6902930A (es) *	1968-02-29	1969-09-02
DE1915387A1 (de) *	1969-03-26	1970-10-01	Basf Ag	Herbizid
DE2503699C2 (de) *	1975-01-30	1983-04-21	Basf Ag, 6700 Ludwigshafen	Verfahren zur Herstellung von 1,2- Benzisothiazolen
DE3018108A1 (de) *	1980-05-12	1981-11-19	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von 1,2-benzisothhiazolen
EP0217747B1 (de) *	1985-09-30	1991-11-21	Ciba-Geigy Ag	Nematizide Mittel
ES2034371T3 (es) *	1987-12-18	1993-04-01	Ciba-Geigy Ag	Procedimiento para la preparacion de 2-tio-5-difluormetiltio-1,3,4-tiadiazol y productos nematocidas.
TW241263B (es) *	1991-08-22	1995-02-21	Hoechst Roussel Pharma

1991
- 1991-04-11 US US07/684,549 patent/US5169951A/en not_active Expired - Lifetime
- 1991-04-16 DK DK91810284T patent/DK0454621T3/da not_active Application Discontinuation
- 1991-04-16 EP EP91810284A patent/EP0454621B1/de not_active Expired - Lifetime
- 1991-04-16 AT AT91810284T patent/ATE194604T1/de not_active IP Right Cessation
- 1991-04-16 DE DE59109193T patent/DE59109193D1/de not_active Expired - Lifetime
- 1991-04-16 ES ES91810284T patent/ES2148146T3/es not_active Expired - Lifetime
- 1991-04-16 KR KR1019910006072A patent/KR0168442B1/ko not_active Expired - Lifetime
- 1991-04-16 SG SG1996003180A patent/SG47031A1/en unknown
- 1991-04-19 CA CA002040889A patent/CA2040889C/en not_active Expired - Lifetime
- 1991-04-19 NZ NZ237888A patent/NZ237888A/xx unknown
- 1991-04-22 AU AU75245/91A patent/AU636738B2/en not_active Expired
- 1991-04-22 IL IL9791091A patent/IL97910A/en not_active IP Right Cessation
- 1991-04-22 IE IE133491A patent/IE911334A1/en not_active IP Right Cessation
- 1991-04-22 TR TR91/0408A patent/TR26713A/xx unknown
- 1991-04-22 PT PT97431A patent/PT97431B/pt not_active IP Right Cessation
- 1991-04-22 BR BR919101605A patent/BR9101605A/pt not_active IP Right Cessation
- 1991-04-23 JP JP3119335A patent/JP3008035B2/ja not_active Expired - Lifetime
1994
- 1994-06-14 US US08/259,719 patent/US5447945A/en not_active Expired - Lifetime
1997
- 1997-01-22 JP JP9023328A patent/JPH09188668A/ja active Pending
- 1997-01-22 JP JP9023327A patent/JPH09194454A/ja active Pending
2000
- 2000-07-21 GR GR20000401673T patent/GR3033987T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0454621A3 (en)	1992-01-22
IL97910A0 (en)	1992-06-21
CA2040889C (en)	2002-04-09
JPH09188668A (ja)	1997-07-22
JP3008035B2 (ja)	2000-02-14
KR910017935A (ko)	1991-11-30
US5169951A (en)	1992-12-08
ATE194604T1 (de)	2000-07-15
NZ237888A (en)	1993-08-26
AU636738B2 (en)	1993-05-06
TR26713A (tr)	1995-05-15
ES2148146T3 (es)	2000-10-16
JPH04225967A (ja)	1992-08-14
PT97431A (pt)	1991-12-31
KR0168442B1 (ko)	1999-01-15
DE59109193D1 (de)	2000-08-17
EP0454621B1 (de)	2000-07-12
US5447945A (en)	1995-09-05
AU7524591A (en)	1991-10-24
GR3033987T3 (en)	2000-11-30
JPH09194454A (ja)	1997-07-29
CA2040889A1 (en)	1991-10-24
IE911334A1 (en)	1991-10-23
EP0454621A2 (de)	1991-10-30
DK0454621T3 (da)	2000-11-06
PT97431B (pt)	1998-08-31
SG47031A1 (en)	1998-03-20
BR9101605A (pt)	1991-12-10

Legal Events

Date	Code	Title
1997-07-13	KB	Patent renewed
1998-02-08	HC	Change of name of proprietor(s)
2001-07-24	KB	Patent renewed
2005-06-19	KB	Patent renewed
2009-09-15	KB	Patent renewed
2011-12-29	EXP	Patent expired

Publication	Publication Date	Title
CA2040889C (en)	2002-04-09	Nematicidal compositions comprising nitro-or halo-benzisothiazoles
EP0059536B1 (en)	1987-04-22	Amide derivatives, processes for preparing them, their use as fungicides and pesticidal compositions containing them
EP0171768A1 (en)	1986-02-19	Substituted propargyloxyacetonitrile derivatives, process for production thereof, and herbicide and agricultural-horticultural fungicide comprising said derivatives as active ingredients
JPH08504781A (ja)	1996-05-21	４−ベンゾイルイソオキサゾール誘導体及び除草剤としてのその使用
JPH06172348A (ja)	1994-06-21	有害生物防除剤
GB2043062A (en)	1980-10-01	N-(heterocyclyl)-acetanilide derivatives and herbicidal and plant growth regulating compositions containing them
JPH05178844A (ja)	1993-07-20	除草性化合物
US4897415A (en)	1990-01-30	2-imino-1,3-dithietanes, their use as pesticides
US5451595A (en)	1995-09-19	Nematicidal compositions
US4861367A (en)	1989-08-29	2-Mercapto-5-pyrazinyl-1,3,4-oxadiazoles or 2-mercapto-5-pyrazinyl-1,3,4-thiadiazoles as nematicides
US4861787A (en)	1989-08-29	Nematicidal compositions
JPH07133266A (ja)	1995-05-23	３−ｎ−置換キナゾリノン誘導体、その製造法および該化合物を含有する除草剤
KR910006448B1 (ko)	1991-08-26	복소환 화합물, 그의 제조방법 및 그를 유효성분으로서 함유하는 제초제 조성물
EP0427445B1 (en)	1994-06-08	Benzylideneaminoxyalkanoic acid (thio) amide derivative, process for preparing the same and herbicide
US4910210A (en)	1990-03-20	Nematicidal compositions
JPH03169872A (ja)	1991-07-23	植物を病気から保護するための組成物
US4394155A (en)	1983-07-19	Substituted pyridine 1-oxide herbicides
US5190945A (en)	1993-03-02	Azinyliminodithietanes and their fungicidal and nematocidal methods of use
EP0604602A1 (en)	1994-07-06	N-(difluoro benzodioxolyl)-2-pyrrolidones, as herbicides
IE910156A1 (en)	1991-07-31	Nematicidal and fungicidal compositions
CA2012499A1 (en)	1990-09-21	Nematicidal and fungicidal compositions
CS195315B2 (en)	1980-01-31	Herbicides and method of preparing active substances therefor
JPH06157499A (ja)	1994-06-03	Ｎ−（１−置換エチル）−２，２−ジクロロシクロプロパンカルボキサミド誘導体及び農園芸用殺菌剤
JPH1095772A (ja)	1998-04-14	２，６−ジクロロイソニコチン酸エステル誘導体及び農薬
JPH01175979A (ja)	1989-07-12	Ｎ−フェニルテトラヒドロフタルイミド誘導体、その製造方法及びそれを有効成分として含有する除草剤