IL99398A - Herbicidal synergistic preparations containing sulfonylureas and a consequence of 1,3,4 (-thiaziazolo] A-3,4 [pyridazine - Google Patents

Herbicidal synergistic preparations containing sulfonylureas and a consequence of 1,3,4 (-thiaziazolo] A-3,4 [pyridazine

Info

Publication number: IL99398A
Authority: IL; Israel
Prior art keywords: hydrogen; crc4alkyl; c4alkyl; formula; crc4alkoxy
Prior art date: 1990-09-06

Application number

IL9939891A

Other languages

English (en)

Hebrew (he)

Original Assignee

Ciba Geigy

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.)

1990-09-06

Filing date

1991-09-04

Publication date

1995-08-31

1991-09-04 Application filed by Ciba Geigy filed Critical Ciba Geigy

1995-08-31 Publication of IL99398A publication Critical patent/IL99398A/en

Links

YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 title claims abstract description 21
239000000203 mixture Substances 0.000 title claims description 89
229940100389 Sulfonylurea Drugs 0.000 title claims description 35
230000002363 herbicidal effect Effects 0.000 title claims description 17
230000002195 synergetic effect Effects 0.000 title description 11
FBFSGJYYCGBKAN-UHFFFAOYSA-N 1,3-dihydro-[1,3,4]thiadiazolo[3,4-a]pyridazine Chemical class C1=CC=CN2CSCN21 FBFSGJYYCGBKAN-UHFFFAOYSA-N 0.000 title description 2
239000001257 hydrogen Substances 0.000 claims abstract description 98
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 98
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 32
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 30
239000001301 oxygen Substances 0.000 claims abstract description 30
229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
241000196324 Embryophyta Species 0.000 claims abstract description 21
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 17
240000008042 Zea mays Species 0.000 claims abstract description 11
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims abstract description 11
235000002017 Zea mays subsp mays Nutrition 0.000 claims abstract description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
235000009973 maize Nutrition 0.000 claims abstract description 11
238000000034 method Methods 0.000 claims abstract description 10
235000013339 cereals Nutrition 0.000 claims abstract description 9
244000068988 Glycine max Species 0.000 claims abstract description 8
235000010469 Glycine max Nutrition 0.000 claims abstract description 8
125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
125000001544 thienyl group Chemical group 0.000 claims abstract description 7
244000045561 useful plants Species 0.000 claims abstract description 7
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 108
-1 dimethoxymethyl Chemical group 0.000 claims description 85
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 76
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 62
229910052736 halogen Inorganic materials 0.000 claims description 47
150000002367 halogens Chemical group 0.000 claims description 47
239000004202 carbamide Substances 0.000 claims description 44
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 32
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 31
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 31
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
229910052717 sulfur Inorganic materials 0.000 claims description 26
239000011593 sulfur Substances 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 24
239000000460 chlorine Substances 0.000 claims description 21
229910052801 chlorine Inorganic materials 0.000 claims description 21
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
125000004438 haloalkoxy group Chemical group 0.000 claims description 9
125000001188 haloalkyl group Chemical group 0.000 claims description 9
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
240000007594 Oryza sativa Species 0.000 claims description 4
235000007164 Oryza sativa Nutrition 0.000 claims description 4
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 4
235000009566 rice Nutrition 0.000 claims description 4
MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 4
125000005504 styryl group Chemical group 0.000 claims description 4
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 claims description 3
125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000000232 haloalkynyl group Chemical group 0.000 claims description 3
125000005059 halophenyl group Chemical group 0.000 claims description 3
QMDDYRTXFMBFBS-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 QMDDYRTXFMBFBS-UHFFFAOYSA-N 0.000 claims description 3
ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
IYTXKIXETAELAV-UHFFFAOYSA-N Aethyl-n-hexyl-keton Natural products CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 claims 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
230000008635 plant growth Effects 0.000 claims 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
235000010716 Vigna mungo Nutrition 0.000 abstract description 4
240000001417 Vigna umbellata Species 0.000 abstract description 4
235000011453 Vigna umbellata Nutrition 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 3
IMUPLNOOXQMRMZ-UHFFFAOYSA-N 1,3,5,6,7,8-hexahydro-[1,3,4]thiadiazolo[3,4-a]pyridazine Chemical compound C1CCCN2CSCN21 IMUPLNOOXQMRMZ-UHFFFAOYSA-N 0.000 abstract 1
BHKWBDLLRADTHN-UHFFFAOYSA-N 1,3,7,8-tetrahydro-[1,3,4]thiadiazolo[3,4-a]pyridazine Chemical compound C1=CCCN2CSCN21 BHKWBDLLRADTHN-UHFFFAOYSA-N 0.000 abstract 1
239000005864 Sulphur Substances 0.000 abstract 1
125000003373 pyrazinyl group Chemical group 0.000 abstract 1
239000012747 synergistic agent Substances 0.000 abstract 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000004480 active ingredient Substances 0.000 description 26
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 12
239000002904 solvent Substances 0.000 description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000004094 surface-active agent Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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 9
238000001704 evaporation Methods 0.000 description 9
235000015424 sodium Nutrition 0.000 description 9
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000007787 solid Substances 0.000 description 8
230000008020 evaporation Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
241000209140 Triticum Species 0.000 description 6
235000021307 Triticum Nutrition 0.000 description 6
239000002671 adjuvant Substances 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
238000009472 formulation Methods 0.000 description 6
229910052740 iodine Chemical group 0.000 description 6
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
150000002170 ethers Chemical class 0.000 description 5
239000002736 nonionic surfactant Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
235000012211 aluminium silicate Nutrition 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000000969 carrier Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
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 4
238000002156 mixing Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
XBXHEDNNWSJZPK-UHFFFAOYSA-N chlorosulfonyloxybenzene Chemical class ClS(=O)(=O)OC1=CC=CC=C1 XBXHEDNNWSJZPK-UHFFFAOYSA-N 0.000 description 3
HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
150000004665 fatty acids Chemical class 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
150000002430 hydrocarbons Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
YRBVTKNYZQOPDE-UHFFFAOYSA-N o-(oxetan-3-yl) 2-propan-2-ylbenzenecarbothioate Chemical compound CC(C)C1=CC=CC=C1C(=S)OC1COC1 YRBVTKNYZQOPDE-UHFFFAOYSA-N 0.000 description 3
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
QMLWSAXEQSBAAQ-UHFFFAOYSA-N oxetan-3-ol Chemical compound OC1COC1 QMLWSAXEQSBAAQ-UHFFFAOYSA-N 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229920002545 silicone oil Polymers 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000004546 suspension concentrate Substances 0.000 description 3
235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000008158 vegetable oil Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
BSGLKJAXBCHKOQ-UHFFFAOYSA-N 2-propan-2-ylbenzenecarbothioic s-acid Chemical compound CC(C)C1=CC=CC=C1C(O)=S BSGLKJAXBCHKOQ-UHFFFAOYSA-N 0.000 description 2
HLUGXOQWZICRTA-UHFFFAOYSA-N 2-propan-2-ylbenzenecarbothioyl chloride Chemical compound CC(C)C1=CC=CC=C1C(Cl)=S HLUGXOQWZICRTA-UHFFFAOYSA-N 0.000 description 2
VATNSVZJQOBOIF-UHFFFAOYSA-N 2h-triazin-1-yl carbamate Chemical compound NC(=O)ON1NN=CC=C1 VATNSVZJQOBOIF-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000005452 alkenyloxyalkyl group Chemical group 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
125000005133 alkynyloxy group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 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
229940105329 carboxymethylcellulose Drugs 0.000 description 2
239000003093 cationic surfactant Substances 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000007931 coated granule Substances 0.000 description 2
239000003240 coconut oil Substances 0.000 description 2
235000019864 coconut oil Nutrition 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000000227 grinding Methods 0.000 description 2
230000009036 growth inhibition Effects 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
GFUFETYGCVQXBV-UHFFFAOYSA-N methyl 2-(2-chloro-4-fluoro-5-isothiocyanatobenzenecarbothioyl)oxyacetate Chemical compound COC(=O)COC(=S)C1=CC(N=C=S)=C(F)C=C1Cl GFUFETYGCVQXBV-UHFFFAOYSA-N 0.000 description 2
LWXCOIFXVJXCPA-UHFFFAOYSA-N methyl 2-(2-chloro-4-fluoro-5-nitrobenzenecarbothioyl)oxyacetate Chemical compound COC(=O)COC(=S)C1=CC([N+]([O-])=O)=C(F)C=C1Cl LWXCOIFXVJXCPA-UHFFFAOYSA-N 0.000 description 2
KEINKAFEKOTQKP-UHFFFAOYSA-N methyl 2-(5-amino-2-chloro-4-fluorobenzenecarbothioyl)oxyacetate Chemical compound COC(=O)COC(=S)C1=CC(N)=C(F)C=C1Cl KEINKAFEKOTQKP-UHFFFAOYSA-N 0.000 description 2
KCCDELLBUOREGS-UHFFFAOYSA-N methyl 2-[2-chloro-5-(diazinane-1-carbothioylamino)-4-fluorobenzenecarbothioyl]oxyacetate Chemical compound C1=C(Cl)C(C(=S)OCC(=O)OC)=CC(NC(=S)N2NCCCC2)=C1F KCCDELLBUOREGS-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
OHAXOTJFANLXGC-UHFFFAOYSA-N oxetan-3-yl 2-chlorosulfonyloxybenzoate Chemical compound ClS(=O)(=O)OC1=CC=CC=C1C(=O)OC1COC1 OHAXOTJFANLXGC-UHFFFAOYSA-N 0.000 description 2
FGXMGZDXXPFRPN-UHFFFAOYSA-N oxetan-3-yl 2-sulfamoylbenzoate Chemical compound NS(=O)(=O)C1=CC=CC=C1C(=O)OC1COC1 FGXMGZDXXPFRPN-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000004892 pyridazines Chemical class 0.000 description 2
239000010499 rapseed oil Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000000344 soap Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
235000012424 soybean oil Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000009736 wetting Methods 0.000 description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
HYNDYAQJODYUGF-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1NCCCN2CCCC=C21 HYNDYAQJODYUGF-UHFFFAOYSA-N 0.000 description 1
SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
QWZBQVKBIOPFFQ-UHFFFAOYSA-N 1-[2-(2,2-difluoroethylsulfanyl)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)SCC(F)F)=N1 QWZBQVKBIOPFFQ-UHFFFAOYSA-N 0.000 description 1
WRWDSJJKXIJCRO-UHFFFAOYSA-N 1-isocyanato-2h-triazine Chemical compound O=C=NN1NN=CC=C1 WRWDSJJKXIJCRO-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
IHEPGSXLLLUYDW-UHFFFAOYSA-N 2-chloro-4-fluoro-5-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=C(Cl)C=C1F IHEPGSXLLLUYDW-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
FQVVJFIHGLIEBJ-UHFFFAOYSA-N 2-chlorosulfonylbenzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1S(Cl)(=O)=O FQVVJFIHGLIEBJ-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#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
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
RZRAKAPVDKRJKW-UHFFFAOYSA-N 2-isothiocyanatobenzoic acid Chemical class OC(=O)C1=CC=CC=C1N=C=S RZRAKAPVDKRJKW-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-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
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
241000219144 Abutilon Species 0.000 description 1
241000219318 Amaranthus Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
239000002028 Biomass Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000219312 Chenopodium Species 0.000 description 1
235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
244000098897 Chenopodium botrys Species 0.000 description 1
235000005490 Chenopodium botrys Nutrition 0.000 description 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
244000182067 Fraxinus ornus Species 0.000 description 1
241001101998 Galium Species 0.000 description 1
235000021506 Ipomoea Nutrition 0.000 description 1
241000207783 Ipomoea Species 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 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
229910019142 PO4 Inorganic materials 0.000 description 1
235000011096 Papaver Nutrition 0.000 description 1
240000001090 Papaver somniferum Species 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
235000007238 Secale cereale Nutrition 0.000 description 1
244000082988 Secale cereale Species 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000207763 Solanum Species 0.000 description 1
235000002634 Solanum 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
240000006394 Sorghum bicolor Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
240000005592 Veronica officinalis Species 0.000 description 1
241001506766 Xanthium Species 0.000 description 1
WUMITRRFRIONMJ-UHFFFAOYSA-N [2-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)phenyl] carbamate Chemical compound COC1=NC(C)=NC(C=2C(=CC=CC=2)OC(N)=O)=N1 WUMITRRFRIONMJ-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
229960000892 attapulgite Drugs 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
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-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
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000011449 brick Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
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 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 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
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-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
238000010410 dusting Methods 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
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
150000005452 ethyl sulfates Chemical class 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
239000008098 formaldehyde solution 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
125000000262 haloalkenyl group Chemical group 0.000 description 1
125000005291 haloalkenyloxy group Chemical group 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
150000005451 methyl sulfates Chemical class 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 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
150000002825 nitriles Chemical class 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
239000003960 organic solvent Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
230000000704 physical effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000008262 pumice Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
239000004576 sand Substances 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
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
239000002689 soil Substances 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
239000007921 spray 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
239000008117 stearic acid Chemical class 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003760 tallow Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
YCGJWFCBFZPGJK-UHFFFAOYSA-N thietan-3-ol Chemical compound OC1CSC1 YCGJWFCBFZPGJK-UHFFFAOYSA-N 0.000 description 1
238000003971 tillage Methods 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Landscapes

Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicines Containing Plant Substances (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

IL9939891A 1990-09-06 1991-09-04 Herbicidal synergistic preparations containing sulfonylureas and a consequence of 1,3,4 (-thiaziazolo] A-3,4 [pyridazine IL99398A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH289090		1990-09-06

Publications (1)

Publication Number	Publication Date
IL99398A true IL99398A (en)	1995-08-31

Family

ID=4243900

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9939891A IL99398A (en)	1990-09-06	1991-09-04	Herbicidal synergistic preparations containing sulfonylureas and a consequence of 1,3,4 (-thiaziazolo] A-3,4 [pyridazine

Country Status (29)

Country	Link
US (1)	US5310722A (pl)
EP (1)	EP0480871B1 (pl)
JP (1)	JP3362142B2 (pl)
KR (1)	KR920005843A (pl)
CN (1)	CN1059446A (pl)
AT (1)	ATE131350T1 (pl)
AU (1)	AU638601B2 (pl)
BG (1)	BG61097B1 (pl)
BR (1)	BR9103843A (pl)
CA (1)	CA2050653A1 (pl)
DE (1)	DE59107075D1 (pl)
ES (1)	ES2081460T3 (pl)
GR (1)	GR3018520T3 (pl)
HR (1)	HRP940513A2 (pl)
HU (1)	HU209535B (pl)
ID (1)	ID860B (pl)
IE (1)	IE69856B1 (pl)
IL (1)	IL99398A (pl)
MX (1)	MX9100942A (pl)
MY (1)	MY136106A (pl)
NZ (1)	NZ239660A (pl)
PL (1)	PL169764B1 (pl)
PT (1)	PT98857B (pl)
RO (1)	RO109270B1 (pl)
RU (1)	RU2041628C1 (pl)
SI (1)	SI9111478A (pl)
TW (1)	TW225471B (pl)
YU (1)	YU147891A (pl)
ZA (1)	ZA917045B (pl)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6017851A (en) *	1992-05-06	2000-01-25	Novartis Corp.	Synergistic composition and process for selective weed control
NZ252686A (en) *	1992-05-06	1995-10-26	Ciba Geigy Ag	Herbicidal composition comprising n-(2-(3,3,3,-trifluoropropyl)-phenylsulphonyl]-n'-(4-methoxy-6 -methyl-1,3,5-triazin-2-yl)urea and a synergistic amount of at least one of various other herbicides
AU3387395A (en) *	1994-09-06	1996-03-29	Novartis Ag	Herbicidal synergistic composition and method of weed conrol
AU714596B2 (en) *	1994-09-13	2000-01-06	Wm. Wrigley Jr. Company	Continuous chewing gum manufacture from base concentrate
DE10022400C5 (de)	2000-04-20	2008-11-06	Jungheinrich Ag	Gabelhubwagen mit einem Fünfradfahrwerk
DE10160139A1 (de) *	2001-12-07	2003-06-18	Bayer Cropscience Gmbh	Synergistische herbizide Mittel enthaltend bestimmte Herbizide aus der Gruppe der Benzoylcylohexandione
KR100750288B1 (ko) *	2006-04-04	2007-08-20	한국화학연구원	제초활성을 가지는테트라하이드로티아디아졸로피리다지논계 화합물
EP2052612A1 (de) *	2007-10-24	2009-04-29	Bayer CropScience AG	Herbizid-Kombination
CN101926351A (zh) *	2010-09-13	2010-12-29	尹小根	含有嗪草酸甲酯的除草组合物
CN103073507A (zh) *	2013-01-07	2013-05-01	深圳大学	一种磺酰脲类化合物

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1330438C (en) *	1980-07-17	1994-06-28	Willy Meyer	N-phenylsulfonyl-n'-pyrimidinyl-and-triazinylureas
US4443243A (en) *	1981-07-16	1984-04-17	Ciba-Geigy Corporation	N-Phenylsulfonyl-N-triazinylureas
US4545811A (en) *	1981-08-06	1985-10-08	Ciba-Geigy Corporation	N-Phenylsulfonyl-N'-triazinyl-ureas
US4579584A (en) *	1981-10-13	1986-04-01	Ciba-Geigy Corporation	N-phenylsulfonyl-N'-triazinylureas
US4478635A (en) *	1982-01-11	1984-10-23	Ciba-Geigy Corporation	N-Arylsulfonyl-N'-pyrimidinylureas
US4618363A (en) *	1982-01-25	1986-10-21	Ciba-Geigy Corporation	N-phenylsulfonyl-N'-triazinylureas
US4537618A (en) *	1982-05-26	1985-08-27	Ciba Geigy Corporation	N-phenylsulfonyl-N'-pyrimidinylureas
EP0096003B2 (de) *	1982-05-28	1994-06-15	Ciba-Geigy Ag	Neue Sulfonyl(thio)harnstoffe, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und/oder Wachstumsregulatoren
MA19797A1 (fr) *	1982-06-14	1983-12-31	Ciba Geigy Ag	N-heterocyclosulfonyl -n- pyrimidinyl et triazinylurees .
DE3372366D1 (de) *	1982-07-16	1987-08-13	Ciba Geigy Ag	N-arylsulfonyl-n'-triazolyl urea
US4780125A (en) *	1982-09-01	1988-10-25	Ciba-Geigy Corporation	N-phenylsulfonyl-N'-triazinylureas
US4515626A (en) *	1982-10-06	1985-05-07	Ciba Geigy Corporation	N-(Cyclopropyl-triazinyl-n'-(arylsulfonyl) ureas having herbicidal activity
DE3472881D1 (de) *	1983-03-28	1988-09-01	Ciba Geigy Ag	N-phenylsulfonyl-n'-pyrimidinyl- and -triazinyl urea
DE3479213D1 (en) *	1983-05-16	1989-09-07	Ciba Geigy Ag	Herbicidally active and plant growth regulating pyrimidine derivatives, their preparation and use
ATE38382T1 (de) *	1984-07-26	1988-11-15	Ciba Geigy Ag	N-arylsulfonyl-n'-triazinyl- und pyrimidinylharnstoffe.
US4759791A (en) *	1985-06-18	1988-07-26	Ciba-Geigy Corporation	N-heterocyclosulfonyl-N'-pyrimidinylureas
EP0238711B1 (en) *	1986-03-25	1990-11-28	Kumiai Chemical Industry Co., Ltd.	Thiadiazabicyclononane derivatives, processes for their production and herbizidal compositions
DE3775686D1 (de) *	1986-09-26	1992-02-13	Ciba Geigy Ag	Aminopyrazinone und aminotriazinone.
US4927450A (en) *	1986-11-28	1990-05-22	Ciba-Geigy Corporation	N-heterocyclosulfonyl-n'-pyrimidinylureas
US4885023A (en) *	1986-12-24	1989-12-05	Kumiai Chemical Industry Co., Ltd.	Thiadiazabicyclononane derivatives and herbicidal compositions
EP0298901B1 (de) *	1987-07-10	1992-01-15	Hoechst Aktiengesellschaft	Herbizide Mittel
CA1309716C (en) *	1987-08-28	1992-11-03	Jun Satow	Condensed heterocyclic derivative, process for their production and herbicides
DE3889412T2 (de) *	1987-10-16	1994-12-22	Ihara Chemical Ind Co	Thiadiazabicyclononanderivate und herbizide Zubereitungen.

1991
- 1991-08-23 MY MYPI91001534A patent/MY136106A/en unknown
- 1991-08-27 EP EP91810684A patent/EP0480871B1/de not_active Expired - Lifetime
- 1991-08-27 DE DE59107075T patent/DE59107075D1/de not_active Expired - Fee Related
- 1991-08-27 AT AT91810684T patent/ATE131350T1/de not_active IP Right Cessation
- 1991-08-27 ES ES91810684T patent/ES2081460T3/es not_active Expired - Lifetime
- 1991-09-04 CA CA002050653A patent/CA2050653A1/en not_active Abandoned
- 1991-09-04 SI SI9111478A patent/SI9111478A/sl unknown
- 1991-09-04 PL PL91291619A patent/PL169764B1/pl unknown
- 1991-09-04 YU YU147891A patent/YU147891A/sh unknown
- 1991-09-04 IL IL9939891A patent/IL99398A/en not_active IP Right Cessation
- 1991-09-04 NZ NZ239660A patent/NZ239660A/xx unknown
- 1991-09-04 MX MX9100942A patent/MX9100942A/es unknown
- 1991-09-04 BG BG95074A patent/BG61097B1/bg unknown
- 1991-09-04 PT PT98857A patent/PT98857B/pt not_active IP Right Cessation
- 1991-09-05 BR BR919103843A patent/BR9103843A/pt not_active Application Discontinuation
- 1991-09-05 KR KR1019910015643A patent/KR920005843A/ko not_active Application Discontinuation
- 1991-09-05 HU HU912876A patent/HU209535B/hu not_active IP Right Cessation
- 1991-09-05 ZA ZA917045A patent/ZA917045B/xx unknown
- 1991-09-05 RU SU915001504A patent/RU2041628C1/ru active
- 1991-09-05 AU AU83674/91A patent/AU638601B2/en not_active Ceased
- 1991-09-05 CN CN91108680A patent/CN1059446A/zh active Pending
- 1991-09-05 RO RO148338A patent/RO109270B1/ro unknown
- 1991-09-05 IE IE312991A patent/IE69856B1/en not_active IP Right Cessation
- 1991-09-05 TW TW080107046A patent/TW225471B/zh active
- 1991-09-06 JP JP25456191A patent/JP3362142B2/ja not_active Expired - Fee Related
- 1991-10-31 ID IDP78791A patent/ID860B/id unknown
1992
- 1992-08-17 US US07/931,120 patent/US5310722A/en not_active Expired - Fee Related
1994
- 1994-09-08 HR HRP-1478/91A patent/HRP940513A2/hr not_active Application Discontinuation
1995
- 1995-12-21 GR GR950403653T patent/GR3018520T3/el unknown

Also Published As

Publication number	Publication date
EP0480871B1 (de)	1995-12-13
PT98857A (pt)	1992-08-31
HRP940513A2 (en)	1997-04-30
ATE131350T1 (de)	1995-12-15
NZ239660A (en)	1993-11-25
PT98857B (pt)	1999-02-26
US5310722A (en)	1994-05-10
IE913129A1 (en)	1992-03-11
BG61097B1 (bg)	1996-11-29
JPH0717814A (ja)	1995-01-20
ES2081460T3 (es)	1996-03-16
MX9100942A (es)	1992-05-04
HUT58470A (en)	1992-03-30
TW225471B (pl)	1994-06-21
IE69856B1 (en)	1996-10-16
AU8367491A (en)	1992-03-12
DE59107075D1 (de)	1996-01-25
BR9103843A (pt)	1992-05-26
HU209535B (en)	1994-07-28
AU638601B2 (en)	1993-07-01
PL169764B1 (pl)	1996-08-30
ID860B (id)	1996-08-06
GR3018520T3 (en)	1996-03-31
CA2050653A1 (en)	1992-03-07
SI9111478A (en)	1997-10-31
RO109270B1 (ro)	1995-01-30
MY136106A (en)	2008-08-29
HU912876D0 (en)	1992-01-28
ZA917045B (en)	1992-05-27
CN1059446A (zh)	1992-03-18
KR920005843A (ko)	1992-04-27
YU147891A (sh)	1994-06-10
EP0480871A3 (en)	1992-10-07
JP3362142B2 (ja)	2003-01-07
BG95074A (bg)	1993-12-24
RU2041628C1 (ru)	1995-08-20
EP0480871A2 (de)	1992-04-15

Legal Events

Date	Code	Title
1998-02-08	HC	Change of name of proprietor(s)
1998-02-22	KB	Patent renewed
2002-05-23	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US4966622A (en)	1990-10-30	N-phenyl-N-pyrimidin-2-ylureas
RU2102388C1 (ru)	1998-01-20	N-[(1,3,5-триазин-2-ил)аминокарбонил]бензолсульфонамиды или их соли, применимые в сельском хозяйстве, гербицидное средство и способ борьбы с нежелательным ростом растений
US4545811A (en)	1985-10-08	N-Phenylsulfonyl-N'-triazinyl-ureas
AU645389B2 (en)	1994-01-13	Novel sulfonylureas
CA2073446C (en)	2001-11-27	Pyridylsulfonylureas as herbicides and plant growth regulators, processes for their preparation and their use
EP0540697B1 (en)	1998-06-03	Sulfonylureas
CS245785B2 (en)	1986-10-16	Herbicide agent and for plants growth regulation and production method of effective substances
EP0161905B1 (en)	1990-08-01	Herbicidal halopyrimidines
EP0162723B1 (en)	1991-05-29	Herbicidal sulfonamides
DK169919B1 (da)	1995-04-03	Fluoralkoxyaminotriaziner, herbicide præparater indeholdende sådanne forbindelser og metode til bekæmpelse af uønsket plantevækst, navnlig ukrudt i sukkerroer
IL99398A (en)	1995-08-31	Herbicidal synergistic preparations containing sulfonylureas and a consequence of 1,3,4 (-thiaziazolo] A-3,4 [pyridazine
AU617205B2 (en)	1991-11-21	Sulfonylureas with heterocyclic substituents, a process for the preparation thereof, and the use thereof as herbicides or plant-growth regulators
US6413911B1 (en)	2002-07-02	Herbicidal sulfonylureas, their preparation and use
AU656654B2 (en)	1995-02-09	Selective herbicidal composition sulfonylureas
US4589909A (en)	1986-05-20	Benzofuran and benzothiophene sulfonamides
CA1228244A (en)	1987-10-20	Herbicidal composition
EP0111442A1 (de)	1984-06-20	N-2-Heterocyclyl-phenylsulfonyl-N'-pyrimidinyl- und -triazinyl-harnstoffe
EP0235449B1 (en)	1991-09-11	Herbicidal sulfonamides
US5163996A (en)	1992-11-17	Sulfonylureas
CA2042355C (en)	1995-11-14	Sulfamidosulfonylurea derivatives and herbicides
EP0192489B1 (en)	1991-04-10	Herbicidal sulfonamides
IL93777A (en)	1994-11-28	Paneoxysulfonylureas based on Alkyl-Salicylates are converted in mode 3, processes for their preparation and use as herbicides and regulators
AU607140B2 (en)	1991-02-28	Novel phenylsulfonylureas
WO1994003064A1 (en)	1994-02-17	Selective herbicidal composition
US4695310A (en)	1987-09-22	Benzofuran and benzothiophene sulfonamides