CA1150271A - 3-¬5-¬1-(alkyloxy or alkylthio)alkyl, alkynyl, alkenyl, or haloalkyl|-1,3,4- thiadiazol-2-yl|-4-hydroxy-1-methyl-2- imidazolidinones - Google Patents

3-¬5-¬1-(alkyloxy or alkylthio)alkyl, alkynyl, alkenyl, or haloalkyl|-1,3,4- thiadiazol-2-yl|-4-hydroxy-1-methyl-2- imidazolidinones

Info

Publication number: CA1150271A
Authority: CA; Canada
Prior art keywords: recited; compound; carbon atoms; alkyl; methyl
Prior art date: 1979-08-10
Legal status (The legal status 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 status listed.): Expired

Application number

CA000357157A

Other languages

English (en)

French (fr)

Inventor

Jerome M. Lavanish

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

PPG Industries Ohio Inc

Original Assignee

PPG Industries Inc

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.)

1979-08-10

Filing date

1980-07-28

Publication date

1983-07-19

1980-07-28 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1983-07-19 Application granted granted Critical

1983-07-19 Publication of CA1150271A publication Critical patent/CA1150271A/en

Status Expired legal-status Critical Current

Links

125000000217 alkyl group Chemical group 0.000 title claims abstract description 28
125000003342 alkenyl group Chemical group 0.000 title claims abstract description 15
125000000304 alkynyl group Chemical group 0.000 title claims abstract description 15
125000001188 haloalkyl group Chemical group 0.000 title claims abstract description 15
125000004414 alkyl thio group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 115
241000196324 Embryophyta Species 0.000 claims abstract description 52
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
238000000034 method Methods 0.000 claims abstract description 41
125000005997 bromomethyl group Chemical group 0.000 claims abstract description 13
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract description 13
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
239000001301 oxygen Substances 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
125000005999 2-bromoethyl group Chemical group 0.000 claims abstract description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
239000011593 sulfur Chemical group 0.000 claims abstract description 8
229910052717 sulfur Chemical group 0.000 claims abstract description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 10
240000006410 Sida spinosa Species 0.000 claims description 8
235000007320 Avena fatua Nutrition 0.000 claims description 7
240000008853 Datura stramonium Species 0.000 claims description 7
240000002439 Sorghum halepense Species 0.000 claims description 7
235000004977 Brassica sinapistrum Nutrition 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
244000075850 Avena orientalis Species 0.000 claims description 5
244000058871 Echinochloa crus-galli Species 0.000 claims description 5
244000275012 Sesbania cannabina Species 0.000 claims description 5
235000002834 Sida rhombifolia Nutrition 0.000 claims description 5
HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-n-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 claims description 4
244000024671 Brassica kaber Species 0.000 claims description 4
244000298479 Cichorium intybus Species 0.000 claims description 4
235000007542 Cichorium intybus Nutrition 0.000 claims description 4
235000005373 Uvularia sessilifolia Nutrition 0.000 claims description 4
241000209764 Avena fatua Species 0.000 claims description 3
235000014750 Brassica kaber Nutrition 0.000 claims description 3
235000011292 Brassica rapa Nutrition 0.000 claims description 3
241000207783 Ipomoea Species 0.000 claims description 3
235000021506 Ipomoea Nutrition 0.000 claims description 3
240000001549 Ipomoea eriocarpa Species 0.000 claims description 3
235000005146 Ipomoea eriocarpa Nutrition 0.000 claims description 3
235000008515 Setaria glauca Nutrition 0.000 claims description 3
206010037549 Purpura Diseases 0.000 claims description 2
241001672981 Purpura Species 0.000 claims description 2
235000001155 Setaria leucopila Nutrition 0.000 claims description 2
244000010062 Setaria pumila Species 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
244000115721 Pennisetum typhoides Species 0.000 claims 1
235000007195 Pennisetum typhoides Nutrition 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
239000000203 mixture Substances 0.000 description 34
239000000243 solution Substances 0.000 description 32
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
-1 3-[5-[1-t-butoxy-2-bromoethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone Chemical compound 0.000 description 17
239000004009 herbicide Substances 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 15
230000002363 herbicidal effect Effects 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
238000009472 formulation Methods 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
239000013078 crystal Substances 0.000 description 9
229960004132 diethyl ether Drugs 0.000 description 9
229940093499 ethyl acetate Drugs 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
206010061217 Infestation Diseases 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
ZWDVDWPZFSIRJC-UHFFFAOYSA-N 4-hydroxy-3-[5-(1-methoxyethyl)-1,3,4-thiadiazol-2-yl]-1-methylimidazolidin-2-one Chemical compound S1C(C(C)OC)=NN=C1N1C(=O)N(C)CC1O ZWDVDWPZFSIRJC-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
229960000443 hydrochloric acid Drugs 0.000 description 5
235000011167 hydrochloric acid Nutrition 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000000539 dimer Substances 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
RYINSASOMFRELV-UHFFFAOYSA-N 1-(2,2-dimethoxyethyl)-3-[5-(1-methoxyethyl)-1,3,4-thiadiazol-2-yl]-1-methylurea Chemical compound COC(OC)CN(C)C(=O)NC1=NN=C(C(C)OC)S1 RYINSASOMFRELV-UHFFFAOYSA-N 0.000 description 3
GFZVETKAEQPSPF-UHFFFAOYSA-N 2-isocyanato-5-(1-methoxyethyl)-1,3,4-thiadiazole Chemical class COC(C)C1=NN=C(N=C=O)S1 GFZVETKAEQPSPF-UHFFFAOYSA-N 0.000 description 3
ICPWFHKNYYRBSZ-UHFFFAOYSA-N 2-methoxypropanoic acid Chemical compound COC(C)C(O)=O ICPWFHKNYYRBSZ-UHFFFAOYSA-N 0.000 description 3
MWDCBSZUHUONCE-UHFFFAOYSA-N 2-propan-2-yloxypropanoic acid Chemical compound CC(C)OC(C)C(O)=O MWDCBSZUHUONCE-UHFFFAOYSA-N 0.000 description 3
VZQPBOQSEQUOBJ-UHFFFAOYSA-N 5-(1-methoxyethyl)-1,3,4-thiadiazol-2-amine Chemical compound COC(C)C1=NN=C(N)S1 VZQPBOQSEQUOBJ-UHFFFAOYSA-N 0.000 description 3
DDLVOLIFPQWOOK-UHFFFAOYSA-N 5-(1-propan-2-yloxyethyl)-1,3,4-thiadiazol-2-amine Chemical compound CC(C)OC(C)C1=NN=C(N)S1 DDLVOLIFPQWOOK-UHFFFAOYSA-N 0.000 description 3
240000008100 Brassica rapa Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000428 dust Substances 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 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
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 2
XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 2
YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
APVXXJSNXUKJDA-UHFFFAOYSA-N 2-isocyanato-5-(1-propan-2-yloxyethyl)-1,3,4-thiadiazole Chemical class CC(C)OC(C)C1=NN=C(N=C=O)S1 APVXXJSNXUKJDA-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
244000075634 Cyperus rotundus Species 0.000 description 2
FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 2
235000014716 Eleusine indica Nutrition 0.000 description 2
240000005702 Galium aparine Species 0.000 description 2
235000014820 Galium aparine Nutrition 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
241000207890 Ipomoea purpurea Species 0.000 description 2
244000042664 Matricaria chamomilla Species 0.000 description 2
235000007232 Matricaria chamomilla Nutrition 0.000 description 2
235000015225 Panicum colonum Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 2
240000000260 Typha latifolia Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
239000002837 defoliant Substances 0.000 description 2
239000002274 desiccant Substances 0.000 description 2
OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
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229920006395 saturated elastomer Polymers 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
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241000894007 species Species 0.000 description 2
125000005415 substituted alkoxy group Chemical group 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
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SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
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VTWOCLHRMQBXIS-UHFFFAOYSA-N 1-(1,1,4-trimethyl-6-propan-2-yl-2,3-dihydroinden-5-yl)propan-1-one;1-(3,3,7-trimethyl-5-propan-2-yl-1,2-dihydroinden-4-yl)propan-1-one Chemical compound C1=C(C(C)C)C(C(=O)CC)=C2C(C)(C)CCC2=C1C.C1=C(C(C)C)C(C(=O)CC)=C(C)C2=C1C(C)(C)CC2 VTWOCLHRMQBXIS-UHFFFAOYSA-N 0.000 description 1
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GYPNJSBBOATUPK-UHFFFAOYSA-N 2-chloro-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CCl GYPNJSBBOATUPK-UHFFFAOYSA-N 0.000 description 1
GYJQWEIGUGMFMU-UHFFFAOYSA-N 2-chloroethyl n-(3-chlorophenyl)carbamate Chemical compound ClCCOC(=O)NC1=CC=CC(Cl)=C1 GYJQWEIGUGMFMU-UHFFFAOYSA-N 0.000 description 1
LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
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SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
235000005770 birds nest Nutrition 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
235000010310 bull nettle Nutrition 0.000 description 1
235000006263 bur ragweed Nutrition 0.000 description 1
CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 description 1
229950004243 cacodylic acid Drugs 0.000 description 1
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
BIWJNBZANLAXMG-UHFFFAOYSA-N chlordane Chemical compound ClC1=C(Cl)C2(Cl)C3CC(Cl)C(Cl)C3C1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-UHFFFAOYSA-N 0.000 description 1
QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 1
CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
235000003488 common ragweed Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
235000010313 devils tomato Nutrition 0.000 description 1
IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000003966 growth inhibitor Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000008624 imidazolidinones Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
244000144972 livestock Species 0.000 description 1
229960003390 magnesium sulfate Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
MYURAHUSYDVWQA-UHFFFAOYSA-N methyl n'-(4-chlorophenyl)-n,n-dimethylcarbamimidate Chemical compound COC(N(C)C)=NC1=CC=C(Cl)C=C1 MYURAHUSYDVWQA-UHFFFAOYSA-N 0.000 description 1
QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
WKQYAIDXQNGNIQ-UHFFFAOYSA-N n'-(3,4-dichlorophenyl)-n,n-dimethylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=C(Cl)C(Cl)=C1 WKQYAIDXQNGNIQ-UHFFFAOYSA-N 0.000 description 1
JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229940096826 phenylmercuric acetate Drugs 0.000 description 1
NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
239000002373 plant growth inhibitor Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
235000009736 ragweed Nutrition 0.000 description 1
238000009738 saturating Methods 0.000 description 1
235000003513 sheep sorrel Nutrition 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
229940010115 simetone Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
NTOCDDPMRUNYHP-UHFFFAOYSA-M sodium;2-(2,4,5-trichlorophenoxy)ethyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl NTOCDDPMRUNYHP-UHFFFAOYSA-M 0.000 description 1
KISFEBPWFCGRGN-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)ethyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl KISFEBPWFCGRGN-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
235000005765 wild carrot Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA000357157A 1979-08-10 1980-07-28 3-¬5-¬1-(alkyloxy or alkylthio)alkyl, alkynyl, alkenyl, or haloalkyl|-1,3,4- thiadiazol-2-yl|-4-hydroxy-1-methyl-2- imidazolidinones Expired CA1150271A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US6569479A	1979-08-10	1979-08-10
US65,694		1979-08-10

Publications (1)

Publication Number	Publication Date
CA1150271A true CA1150271A (en)	1983-07-19

Family

ID=22064480

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000357157A Expired CA1150271A (en)	1979-08-10	1980-07-28	3-¬5-¬1-(alkyloxy or alkylthio)alkyl, alkynyl, alkenyl, or haloalkyl\|-1,3,4- thiadiazol-2-yl\|-4-hydroxy-1-methyl-2- imidazolidinones

Country Status (21)

Country	Link
AR (1)	AR227767A1 (es)
BG (1)	BG34613A3 (es)
BR (1)	BR8004985A (es)
CA (1)	CA1150271A (es)
CS (1)	CS226018B2 (es)
DD (1)	DD154522A5 (es)
DE (1)	DE3029729C2 (es)
EG (1)	EG14324A (es)
ES (1)	ES8106726A1 (es)
FR (1)	FR2463138A1 (es)
GB (1)	GB2055832B (es)
IT (1)	IT1129241B (es)
MA (1)	MA18930A1 (es)
PH (1)	PH16568A (es)
PL (1)	PL126910B1 (es)
PT (1)	PT71681B (es)
RO (1)	RO80300A (es)
SU (1)	SU961558A3 (es)
YU (1)	YU197880A (es)
ZA (1)	ZA804583B (es)
ZW (1)	ZW18480A1 (es)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR216038A1 (es) *	1973-06-29	1979-11-30	Velsicol Chemical Corp	Nuevos derivados de 1-(1,3,4-tiadiazol-2-il)-3-alquil-5-hidroxi-1,3-imidazolidin-2-onas con actividad herbicida y composiciones herbicidas que los contienen
US4012223A (en) *	1974-01-10	1977-03-15	Velsicol Chemical Corporation	Thiadiazolylimidazolidinones herbicides
FR2257581A1 (en) *	1974-01-10	1975-08-08	Velsicol Chemical Corp	Herbicidal thiadiazolyl imidazolidinones - 1-(2-alkyl-(1,3,4)thiadiazol-5-yl)-3-(halo)alkylimidazolidine-2-o- nes
IL48358A (en) *	1975-04-14	1979-03-12	Velsicol Chemical Corp	1-(5-alkyl-1,3,4-thiadiazol-2-yl)-5-(alkanoyloxy)-3-alkyl-2-imidazolidinones
US4086238A (en) *	1976-06-21	1978-04-25	Velsicol Chemical Corporation	1-Thiadiazolyl-4-methoxymethyl-5-hydroxyimidazolidinones
US4063924A (en) *	1976-10-29	1977-12-20	Velsicol Chemical Corporation	New thiadiazolylimidazolidinone ester
JPS5390519A (en) *	1977-01-18	1978-08-09	Nissan Diesel Motor Co Ltd	Exhaust gas refluxing control device for diesel engine
US4268675A (en) *	1979-07-06	1981-05-19	Ppg Industries, Inc.	3-[5-[1-(Dihalophenoxy)alkyl, alkynyl, alkenyl, or haloalkyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinones

1980
- 1980-07-28 CA CA000357157A patent/CA1150271A/en not_active Expired
- 1980-07-29 ZA ZA00804583A patent/ZA804583B/xx unknown
- 1980-08-05 ZW ZW184/80A patent/ZW18480A1/xx unknown
- 1980-08-06 DE DE3029729A patent/DE3029729C2/de not_active Expired
- 1980-08-06 YU YU01978/80A patent/YU197880A/xx unknown
- 1980-08-07 DD DD80223178A patent/DD154522A5/de unknown
- 1980-08-08 FR FR8017624A patent/FR2463138A1/fr active Granted
- 1980-08-08 PT PT71681A patent/PT71681B/pt unknown
- 1980-08-08 BR BR8004985A patent/BR8004985A/pt unknown
- 1980-08-08 IT IT68277/80A patent/IT1129241B/it active
- 1980-08-08 BG BG048791A patent/BG34613A3/xx unknown
- 1980-08-08 SU SU802962251A patent/SU961558A3/ru active
- 1980-08-08 AR AR282098A patent/AR227767A1/es active
- 1980-08-08 GB GB8025862A patent/GB2055832B/en not_active Expired
- 1980-08-08 ES ES494104A patent/ES8106726A1/es not_active Expired
- 1980-08-09 MA MA19131A patent/MA18930A1/fr unknown
- 1980-08-09 EG EG492/80A patent/EG14324A/xx active
- 1980-08-11 CS CS805529A patent/CS226018B2/cs unknown
- 1980-08-11 RO RO80101954A patent/RO80300A/ro unknown
- 1980-08-11 PL PL1980226187A patent/PL126910B1/pl unknown
- 1980-08-11 PH PH24428A patent/PH16568A/en unknown

Also Published As

Publication number	Publication date
FR2463138A1 (fr)	1981-02-20
ZW18480A1 (en)	1980-10-22
IT1129241B (it)	1986-06-04
MA18930A1 (fr)	1981-04-01
ES494104A0 (es)	1981-08-01
EG14324A (en)	1983-12-31
YU197880A (en)	1983-06-30
ZA804583B (en)	1981-09-30
RO80300A (ro)	1982-12-06
BR8004985A (pt)	1981-02-24
CS226018B2 (en)	1984-03-19
ES8106726A1 (es)	1981-08-01
AR227767A1 (es)	1982-12-15
FR2463138B1 (es)	1983-07-08
GB2055832A (en)	1981-03-11
DE3029729C2 (de)	1982-12-23
PL226187A1 (es)	1981-10-16
PT71681B (en)	1981-06-15
IT8068277A0 (it)	1980-08-08
PL126910B1 (en)	1983-09-30
BG34613A3 (en)	1983-10-15
PH16568A (en)	1983-11-18
SU961558A3 (ru)	1982-09-23
GB2055832B (en)	1983-09-28
DE3029729A1 (de)	1981-03-26
DD154522A5 (de)	1982-03-31
PT71681A (en)	1980-09-01

Publication	Publication Date	Title
US4268679A (en)	1981-05-19	3-[5- or 3-Substituted-5- or 3-isoxazolyl]-1-allyl or alkyl-4-substituted-5-substituted or unsubstituted-2-imidazolidinones
US4302239A (en)	1981-11-24	3-(5- or 3-Substituted-5- or 3-isoxazolyl)-1-allyl or alkyl-4-substituted-5-substituted or unsubstituted-2-imidazolidinones for controlling weeds
US4116670A (en)	1978-09-26	Dioxane substituted amides
US4028375A (en)	1977-06-07	Thiadiazolylimidazolidinones
US4036848A (en)	1977-07-19	1-Thiadiazolyl-5-furfuryl and tetrahydrofurfuryl aminoimidazolidinones
US4289524A (en)	1981-09-15	Herbicidal 3-(tetrahydrobenzothiazol-2-yl)tetrahydro-1,3,5-oxadiazin-4-ones
US3966811A (en)	1976-06-29	Dialkyl acetals of anilinoacetaldehydes
US4110101A (en)	1978-08-29	Dioxepane substituted amides
GB2045754A (en)	1980-11-05	Tetrahydrobenzothiazolyl- imidazolidinones processes for their preparation, and their use as herbicides
US4233057A (en)	1980-11-11	3-[5-(1-Phenoxy-alkyl, -alkynyl, -alkenyl, or haloalkyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinones
US4046554A (en)	1977-09-06	Dialkyl acetals of anilinoacetaldehydes
US4046768A (en)	1977-09-06	1-Thiazolyl-5-pyridylcarbonyloxyimidazolidinones
US3983174A (en)	1976-09-28	Dialkyl acetals of N-α-halocetylanilino aldehydes
US3932410A (en)	1976-01-13	1-Thiadiazolyl-6-alkoxytetrahydropyrimidinones
US3976471A (en)	1976-08-24	N-(alkylideneaminooxymethyl)-alpha-haloacetanilides
US4268675A (en)	1981-05-19	3-[5-[1-(Dihalophenoxy)alkyl, alkynyl, alkenyl, or haloalkyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinones
US4252960A (en)	1981-02-24	Intermediates of and methods of making 3-[5-[1-(nitrophenoxy)alkyl, alkynyl, alkenyl or haloalkyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinones
US4252961A (en)	1981-02-24	Intermediates of and process for making 3-[5-[1-(2-, 3-, or 4-methyl, or ethyl or isopropylphenoxy)alkyl, alkynyl, alkenyl, or haloalkyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinones
CA1150271A (en)	1983-07-19	3-¬5-¬1-(alkyloxy or alkylthio)alkyl, alkynyl, alkenyl, or haloalkyl\|-1,3,4- thiadiazol-2-yl\|-4-hydroxy-1-methyl-2- imidazolidinones
US4264353A (en)	1981-04-28	3-[5-[1-(4-Halophenoxy)alkyl, alkynyl, alkenyl, or haloalkyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinones
US4029491A (en)	1977-06-14	1-Benzothiazolyl-5-hydroxyimidazolidinones
US3988143A (en)	1976-10-26	1-Thiadiazolyl-6-alkoxytetrahydropyrimidinones
US4263041A (en)	1981-04-21	Optionally substituted phenyl, and alkyl N-[5-(2-chloro-4-trifluoromethyl-6-optionally substituted phenoxy)-2-nitro, halo, or cyanobenzoyl]carbamates
US4086240A (en)	1978-04-25	1-Thiazolyl-5-phenoxy and phenylthioalkanoyloxyimidazolidinones
US4045446A (en)	1977-08-30	1-Benzothiazolyl-5-pyridylcarbonyloxyimidazolidinones

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