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
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238000009472 formulation Methods 0.000 description 10
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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
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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
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LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
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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
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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
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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
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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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
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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
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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
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150000001989 diazonium salts Chemical class 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
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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
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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
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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
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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
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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
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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
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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
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231100000053 low toxicity Toxicity 0.000 description 1
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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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Liquid Crystal Substances (AREA)
Dental Preparations (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (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 (fr)
EP (1)	EP0454621B1 (fr)
JP (3)	JP3008035B2 (fr)
KR (1)	KR0168442B1 (fr)
AT (1)	ATE194604T1 (fr)
AU (1)	AU636738B2 (fr)
BR (1)	BR9101605A (fr)
CA (1)	CA2040889C (fr)
DE (1)	DE59109193D1 (fr)
DK (1)	DK0454621T3 (fr)
ES (1)	ES2148146T3 (fr)
GR (1)	GR3033987T3 (fr)
IE (1)	IE911334A1 (fr)
IL (1)	IL97910A (fr)
NZ (1)	NZ237888A (fr)
PT (1)	PT97431B (fr)
SG (1)	SG47031A1 (fr)
TR (1)	TR26713A (fr)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
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DE59205384D1 (de) *	1991-07-17	1996-03-28	Ciba Geigy Ag	Nematizide Mittel
TW241263B (fr) *	1991-08-22	1995-02-21	Hoechst Roussel Pharma
TW268947B (fr) *	1993-09-13	1996-01-21	Ciba Geigy
US6281168B1 (en)	1999-01-19	2001-08-28	American Cyanamid Co.	Herbicidal compositions and method of safening herbicides using benzothiazole derivatives
AU1014300A (en) *	1999-01-19	2000-07-20	American Cyanamid Company	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
AU2003232204B8 (en) *	2002-04-26	2009-07-30	F. Hoffmann-La Roche Ag	Substituted phenylacetamides and their use as glucokinase activators
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
SG153809A1 (en) *	2004-06-07	2009-07-29	Syngenta Participations Ag	Methods of reducing nematode damage
AP2007004296A0 (en) *	2005-06-03	2007-12-31	Basf Ag	Pesticidal mixture
KR101440162B1 (ko)	2006-06-22	2014-09-12	바스프 에스이	말로노니트릴 화합물
JP5525260B2 (ja)	2006-09-14	2014-06-18	ビーエーエスエフソシエタス・ヨーロピア	殺虫剤組成物
JP5877624B2 (ja)	2006-11-10	2016-03-08	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	フィプロニルの結晶変態
EA018341B1 (ru)	2006-11-10	2013-07-30	Басф Се	Новая кристаллическая модификация фипронила и ее применение
WO2008055882A1 (fr)	2006-11-10	2008-05-15	Basf Se	Modification cristalline de fipronil
UA110598C2 (uk)	2006-11-10	2016-01-25	Басф Се	Спосіб одержання кристалічної модифікації фіпронілу
BRPI0719544B1 (pt) *	2006-11-30	2016-03-01	Basf Se	formulação, usos de pelo menos um copolímero, métodos para combater insetos nocivos e/ou fungos fitopatogênicos, para controlar vegetação indesejável e para melhorar a saúde das plantas
WO2008065050A1 (fr) *	2006-11-30	2008-06-05	Basf Se	Formulations agrochimiques comprenant des copolymères à base de diisocyanates
EP2099292B1 (fr) *	2006-11-30	2010-05-26	Basf Se	Préparations agrochimiques contenant des copolymères n-vinylamide
EP2258177A3 (fr)	2006-12-15	2011-11-09	Rohm and Haas Company	Mélanges contenant du methylcyclopropène
EP2066177B1 (fr)	2007-01-19	2014-12-24	Basf Se	Mélanges fongicides constitués d'anilides de l'acide 1-methylpyrazol-4-yl carboxylique et d'azolopyrimidinylamines
KR20090107070A (ko)	2007-01-26	2009-10-12	바스프 에스이	동물 해충 ⅱ의 퇴치를 위한 3-아미노-1,2-벤즈이소티아졸 화합물
EP1952690A3 (fr)	2007-01-31	2009-04-22	Basf Se	Mélanges de pesticides basés sur des triazolopyrimidines et des insecticides
AR065197A1 (es)	2007-02-06	2009-05-20	Basf Se	Insecticidas como safeners para fungicidas con accion fitotoxica
JP5465659B2 (ja)	2007-04-12	2014-04-09	ビーエーエスエフソシエタス・ヨーロピア	シアノスルホキシミン化合物を含む殺虫剤混合物
AU2008240710A1 (en)	2007-04-23	2008-10-30	Basf Se	Plant productivity enhancement by combining chemical agents with transgenic modifications
BRPI0814941A2 (pt)	2007-08-16	2014-09-30	Basf Se	Composição de tratamentode semente, e, método de tratamento de semente.
CA2698560A1 (fr)	2007-09-20	2009-03-26	Basf Se	Combinaisons comprenant une souche fongicide et un compose actif
KR20100105614A (ko) *	2007-12-21	2010-09-29	바스프 에스이	발포성 폴리스티렌으로 이루어진 살충제-함유 입자 및 이들로부터 수득할 수 있는 살충제-함유 성형물
EP2230905A2 (fr) *	2007-12-21	2010-09-29	Basf Se	Procédé d'obtention de perles d'un matériau traité insecticide et constitué d'un polystyrène expansé, et éléments moulés traités insecticide ainsi obtenus
BRPI0906577A2 (pt)	2008-01-25	2019-09-24	Syngenta Partcipations Ag	compostos químicos
US20110201662A1 (en) *	2008-10-22	2011-08-18	Basf Se	Method for producing xps moulded pieces provided with insecticide
CN104381250B (zh)	2009-01-27	2017-04-12	巴斯夫欧洲公司	拌种方法
WO2010089244A1 (fr)	2009-02-03	2010-08-12	Basf Se	Procédé d'engraissement de semences
BRPI1005814A2 (pt)	2009-03-04	2019-09-24	Basf Se	compostos de 3 arilquinazolin 4 ona uso de um composto de 3 arilquinazolin 4 ona da formula i composição agricola metodo para combater pestes de invertebrados material, de propagação de planta , uso de um composto de 3 arilquinazolin 4 ona da formula i e metodo para tratar ou proteger um animal contra infestação ou infecção por parasitas de invertebrados
CN102471321A (zh)	2009-07-06	2012-05-23	巴斯夫欧洲公司	用于防治无脊椎动物害虫的哒嗪化合物
WO2011009804A2 (fr)	2009-07-24	2011-01-27	Basf Se	Composés dérivés de pyridine pour la lutte contre des animaux nuisibles invertébrés
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
CN102812018A (zh)	2010-03-23	2012-12-05	巴斯夫欧洲公司	用于防治无脊椎动物害虫的哒嗪化合物
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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
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
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
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
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
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
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
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
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
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
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1991
- 1991-04-11 US US07/684,549 patent/US5169951A/en not_active Expired - Lifetime
- 1991-04-16 EP EP91810284A patent/EP0454621B1/fr 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
- 1991-04-16 ES ES91810284T patent/ES2148146T3/es not_active Expired - Lifetime
- 1991-04-16 AT AT91810284T patent/ATE194604T1/de not_active IP Right Cessation
- 1991-04-16 DK DK91810284T patent/DK0454621T3/da not_active Application Discontinuation
- 1991-04-16 DE DE59109193T patent/DE59109193D1/de not_active Expired - Lifetime
- 1991-04-19 NZ NZ237888A patent/NZ237888A/xx unknown
- 1991-04-19 CA CA002040889A patent/CA2040889C/fr not_active Expired - Lifetime
- 1991-04-22 PT PT97431A patent/PT97431B/pt not_active IP Right Cessation
- 1991-04-22 TR TR91/0408A patent/TR26713A/xx unknown
- 1991-04-22 BR BR919101605A patent/BR9101605A/pt not_active IP Right Cessation
- 1991-04-22 IL IL9791091A patent/IL97910A/en not_active IP Right Cessation
- 1991-04-22 AU AU75245/91A patent/AU636738B2/en not_active Expired
- 1991-04-22 IE IE133491A patent/IE911334A1/en 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
US5169951A (en)	1992-12-08
DE59109193D1 (de)	2000-08-17
JP3008035B2 (ja)	2000-02-14
JPH09188668A (ja)	1997-07-22
DK0454621T3 (da)	2000-11-06
KR0168442B1 (ko)	1999-01-15
PT97431A (pt)	1991-12-31
EP0454621A2 (fr)	1991-10-30
BR9101605A (pt)	1991-12-10
KR910017935A (ko)	1991-11-30
IL97910A0 (en)	1992-06-21
GR3033987T3 (en)	2000-11-30
SG47031A1 (en)	1998-03-20
EP0454621A3 (en)	1992-01-22
NZ237888A (en)	1993-08-26
EP0454621B1 (fr)	2000-07-12
ATE194604T1 (de)	2000-07-15
JPH09194454A (ja)	1997-07-29
ES2148146T3 (es)	2000-10-16
AU7524591A (en)	1991-10-24
JPH04225967A (ja)	1992-08-14
US5447945A (en)	1995-09-05
AU636738B2 (en)	1993-05-06
TR26713A (tr)	1995-05-15
CA2040889A1 (fr)	1991-10-24
IE911334A1 (en)	1991-10-23
CA2040889C (fr)	2002-04-09
PT97431B (pt)	1998-08-31

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 (fr)	2002-04-09	Compositions nematicides comprenant du nitro-ou halogeno-benzisothiazoles
EP0059536B1 (fr)	1987-04-22	Dérivés d'amides, leurs procédés de préparation, leur utilisation comme fongicides et compositions pesticides les contenant
EP0171768A1 (fr)	1986-02-19	Dérivés substitués du propargyloxy-acétonitrile, procédé de leur préparation, herbicides et fongicides pour l'argriculture et pour l'horticulture les contenant comme agents actifs
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 (fr)	1994-06-08	Dérivés amidés d'acides benzylidène-aminooxyalcane(thi)oiques, procédé pour leur préparation et herbicides
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 (fr)	1994-07-06	N-(difluorobenzodioxolyl)-2-pyrrolidones utiles en tant qu'herbicides
IE910156A1 (en)	1991-07-31	Nematicidal and fungicidal compositions
CA2012499A1 (fr)	1990-09-21	Compositions nematicides et fongicides
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