CA1126734A - Tetrahydrobenzothiazolylimidazolidinones - Google Patents
TetrahydrobenzothiazolylimidazolidinonesInfo
- Publication number
- CA1126734A CA1126734A CA345,912A CA345912A CA1126734A CA 1126734 A CA1126734 A CA 1126734A CA 345912 A CA345912 A CA 345912A CA 1126734 A CA1126734 A CA 1126734A
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydrobenzothiazol
- hydroxy
- imidazolidin
- ethyl
- reaction mixture
- Prior art date
- 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
Links
- FNLMKLJJRWRDRY-UHFFFAOYSA-N 1-(2,3,3a,4-tetrahydro-1,3-benzothiazol-2-yl)imidazolidin-2-one Chemical class O=C1NCCN1C1SC2=CC=CCC2N1 FNLMKLJJRWRDRY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 241000196324 Embryophyta Species 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 36
- 230000002363 herbicidal effect Effects 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 7
- 231100000331 toxic Toxicity 0.000 claims description 4
- 230000002588 toxic effect Effects 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000004009 herbicide Substances 0.000 abstract description 18
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 80
- 239000011541 reaction mixture Substances 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 37
- 239000000047 product Substances 0.000 description 37
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 35
- 239000002244 precipitate Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 29
- 239000011521 glass Substances 0.000 description 26
- -1 2-amino-4,5,6,7-tetrahydrobenzothiazole 2-amino-4-chloro-4,5,6,7-tetrahydrobenzothiazole 2-amino-S-methyl-4,5,6,7-tetrahydrobenzothiazole Chemical compound 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000001914 filtration Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 9
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 208000027418 Wounds and injury Diseases 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000006378 damage Effects 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 208000014674 injury Diseases 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 240000006122 Chenopodium album Species 0.000 description 5
- 235000009344 Chenopodium album Nutrition 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 4
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 4
- 235000004135 Amaranthus viridis Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 4
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000014716 Eleusine indica Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 241000320639 Leptochloa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 241000209072 Sorghum Species 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 240000000321 Abutilon grandifolium Species 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 241000217446 Calystegia sepium Species 0.000 description 3
- 235000005853 Cyperus esculentus Nutrition 0.000 description 3
- 240000001505 Cyperus odoratus Species 0.000 description 3
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 3
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 3
- 235000005476 Digitaria cruciata Nutrition 0.000 description 3
- 235000006830 Digitaria didactyla Nutrition 0.000 description 3
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- 244000025670 Eleusine indica Species 0.000 description 3
- 241000508725 Elymus repens Species 0.000 description 3
- 235000003403 Limnocharis flava Nutrition 0.000 description 3
- 240000004658 Medicago sativa Species 0.000 description 3
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000008515 Setaria glauca Nutrition 0.000 description 3
- 235000001155 Setaria leucopila Nutrition 0.000 description 3
- 244000010062 Setaria pumila Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000002837 defoliant Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- NPVRVHLVKZWQRI-UHFFFAOYSA-N ethyl n-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)carbamate Chemical compound C1CCCC2=C1N=C(NC(=O)OCC)S2 NPVRVHLVKZWQRI-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000012360 testing method Methods 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
- ALUQMCBDQKDRAK-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1,3-benzothiazole Chemical compound C1C=CC=C2SCNC21 ALUQMCBDQKDRAK-UHFFFAOYSA-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
- XLFRSZQTJOSMBQ-UHFFFAOYSA-N 2-(propylamino)acetaldehyde Chemical compound CCCNCC=O XLFRSZQTJOSMBQ-UHFFFAOYSA-N 0.000 description 2
- JGFOGJAJRIKCQN-UHFFFAOYSA-N 2-isocyanato-5,5,7-trimethyl-6,7-dihydro-4h-1,3-benzothiazole Chemical class CC1CC(C)(C)CC2=C1SC(N=C=O)=N2 JGFOGJAJRIKCQN-UHFFFAOYSA-N 0.000 description 2
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000012935 Averaging Methods 0.000 description 2
- 235000011292 Brassica rapa Nutrition 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 241001148727 Bromus tectorum Species 0.000 description 2
- 240000008853 Datura stramonium Species 0.000 description 2
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 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
- 240000007807 Sisymbrium officinale Species 0.000 description 2
- 240000002439 Sorghum halepense Species 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
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
- RPHQUFNKDDZBRT-UHFFFAOYSA-N ethyl n-(5,5,7,7-tetramethyl-4,6-dihydro-1,3-benzothiazol-2-yl)carbamate Chemical compound C1C(C)(C)CC(C)(C)C2=C1N=C(NC(=O)OCC)S2 RPHQUFNKDDZBRT-UHFFFAOYSA-N 0.000 description 2
- JTQJWLLSFLYREC-UHFFFAOYSA-N ethyl n-(7-chloro-5-ethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)carbamate Chemical compound C1C(CC)CC(Cl)C2=C1N=C(NC(=O)OCC)S2 JTQJWLLSFLYREC-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002245 particle 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
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 208000037974 severe injury Diseases 0.000 description 2
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- 238000005507 spraying Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 235000012222 talc Nutrition 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
- 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
- JEZZOKXIXNSKQD-UHFFFAOYSA-N 1,3-bis(4-nitrophenyl)urea Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 JEZZOKXIXNSKQD-UHFFFAOYSA-N 0.000 description 1
- 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
- WLKSPGHQGFFKGE-UHFFFAOYSA-N 1-chloropropan-2-yl n-(3-chlorophenyl)carbamate Chemical compound ClCC(C)OC(=O)NC1=CC=CC(Cl)=C1 WLKSPGHQGFFKGE-UHFFFAOYSA-N 0.000 description 1
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
- XTVIFVALDYTCLL-UHFFFAOYSA-N 2,3,5-trichloro-1h-pyridin-4-one Chemical compound ClC1=CNC(Cl)=C(Cl)C1=O XTVIFVALDYTCLL-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
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- 239000002794 2,4-DB Substances 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- KBQPYERMRVPJDC-UHFFFAOYSA-N 2,4-dichloro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1Cl KBQPYERMRVPJDC-UHFFFAOYSA-N 0.000 description 1
- PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 1
- ISMLHZDOBNLSLN-UHFFFAOYSA-N 2-(2,3,5-trichloro-6-methoxyphenyl)acetic acid Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1CC(O)=O ISMLHZDOBNLSLN-UHFFFAOYSA-N 0.000 description 1
- LGURYBCSJPXHTF-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)ethyl benzoate Chemical compound ClC1=CC(Cl)=CC=C1OCCOC(=O)C1=CC=CC=C1 LGURYBCSJPXHTF-UHFFFAOYSA-N 0.000 description 1
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- CWNIAUXXVGNZGH-UHFFFAOYSA-N 2-(bromomethylamino)acetaldehyde Chemical compound BrCNCC=O CWNIAUXXVGNZGH-UHFFFAOYSA-N 0.000 description 1
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- CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 description 1
- XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-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
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- SNYRXHULAWEECU-UHFFFAOYSA-N 3,4-dichlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C(Cl)=C1 SNYRXHULAWEECU-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- RTWCZQFXFMXXKP-UHFFFAOYSA-N 4-(2,4,5-trichlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC(Cl)=C(Cl)C=C1Cl RTWCZQFXFMXXKP-UHFFFAOYSA-N 0.000 description 1
- SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 0.000 description 1
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
- GEPVLLDBCIZWFD-UHFFFAOYSA-N 5,5,7-trimethyl-6,7-dihydro-4h-1,3-benzothiazol-2-amine Chemical compound CC1CC(C)(C)CC2=C1SC(N)=N2 GEPVLLDBCIZWFD-UHFFFAOYSA-N 0.000 description 1
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- CFXLROUUBGZZKT-UHFFFAOYSA-N ethyl N-(5-ethylsulfanyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)carbamate Chemical compound C(C)SC1CCC2=C(N=C(S2)NC(OCC)=O)C1 CFXLROUUBGZZKT-UHFFFAOYSA-N 0.000 description 1
- ICVPDJYGYNKDQV-UHFFFAOYSA-N ethyl N-(5-ethylsulfanyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)carbamate 5-ethylsulfanyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-amine Chemical compound NC=1SC2=C(N1)CC(CC2)SCC.C(C)SC2CCC1=C(N=C(S1)NC(OCC)=O)C2 ICVPDJYGYNKDQV-UHFFFAOYSA-N 0.000 description 1
- OLPVFENUYZSQSJ-UHFFFAOYSA-N ethyl N-(5-hexyl-7-propoxy-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)carbamate Chemical compound C(CCCCC)C1CC(C2=C(N=C(S2)NC(OCC)=O)C1)OCCC OLPVFENUYZSQSJ-UHFFFAOYSA-N 0.000 description 1
- YOXPKMWSNOTRLO-UHFFFAOYSA-N ethyl n-(7-cyano-5-propyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)carbamate Chemical compound C1C(CCC)CC(C#N)C2=C1N=C(NC(=O)OCC)S2 YOXPKMWSNOTRLO-UHFFFAOYSA-N 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
- 239000000706 filtrate Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003350 kerosene Substances 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
- 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000009526 moderate injury Effects 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
- 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
- 238000010899 nucleation Methods 0.000 description 1
- 239000012430 organic reaction media 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
- 239000000575 pesticide Substances 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 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
- 239000004033 plastic Substances 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
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 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
- 239000002002 slurry Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 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
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 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
-
- 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
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1685479A | 1979-03-02 | 1979-03-02 | |
| US16,854 | 1979-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1126734A true CA1126734A (en) | 1982-06-29 |
Family
ID=21779343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA345,912A Expired CA1126734A (en) | 1979-03-02 | 1980-02-19 | Tetrahydrobenzothiazolylimidazolidinones |
Country Status (18)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175189A (en) * | 1981-04-21 | 1982-10-28 | Kyowa Hakko Kogyo Co Ltd | Benzothiazole derivative and its preparation |
| JPS58110582A (ja) * | 1981-12-24 | 1983-07-01 | Kureha Chem Ind Co Ltd | テトラヒドロベンゾチアゾリルイミダゾリジノン誘導体及び該誘導体を有効成分とする除草剤 |
| DE3246705C2 (de) * | 1981-12-24 | 1986-07-10 | Kureha Kagaku Kogyo K.K., Tokio/Tokyo | Tetrahydrobenzthiazolderivate und diese Verbindungen als wirksamen Bestandteil enthaltende herbizide Mittel |
| US4577029A (en) * | 1982-05-10 | 1986-03-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivative of tetrahydrobenzothiazole and herbicidal composition containing the same as active ingredient |
| JPS59186979A (ja) * | 1983-04-08 | 1984-10-23 | Kureha Chem Ind Co Ltd | テトラヒドロベンゾチアゾ−ル誘導体及び該誘導体を含有する除草剤 |
| DE3407506A1 (de) * | 1984-03-01 | 1985-09-05 | A. Nattermann & Cie GmbH, 5000 Köln | 3-amino-1-(4,5,6,7-tetrahydro-benzothiazolyl)-2-pyrazoline, verfahren zu ihrer herstellung und deren verwendung |
| JPS6317880A (ja) * | 1986-07-09 | 1988-01-25 | Nippon Tokushu Noyaku Seizo Kk | 新規ｎ−ベンゾチアゾリル−２，５−ジヒドロピロ−ル類及び除草剤 |
| ES2245604B1 (es) * | 2004-06-25 | 2006-12-01 | Ragactives, S. L. | Procedimiento para la obtencion de 2-amino-6-alquil-amino-4,5,6,7-tetrahidrobenzotiazoles. |
| CN105873918A (zh) * | 2013-12-23 | 2016-08-17 | 先正达参股股份有限公司 | 具有除草活性的二氢-乙内酰脲衍生物 |
| GB201419827D0 (en) | 2014-11-07 | 2014-12-24 | Syngenta Participations Ag | Herbicidal compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ184082A (en) * | 1976-05-20 | 1980-05-27 | Velsicol Chemical Corp | 1-benzothiazol-2yl-1,3-imidazolidin-2-ones |
-
1980
- 1980-02-07 IL IL59334A patent/IL59334A/xx unknown
- 1980-02-08 AU AU55376/80A patent/AU531808B2/en not_active Ceased
- 1980-02-19 CA CA345,912A patent/CA1126734A/en not_active Expired
- 1980-02-20 NZ NZ192923A patent/NZ192923A/xx unknown
- 1980-02-20 ZA ZA00800978A patent/ZA80978B/xx unknown
- 1980-02-26 IT IT48013/80A patent/IT1127362B/it active
- 1980-02-27 BR BR8001161A patent/BR8001161A/pt unknown
- 1980-02-28 FR FR8004430A patent/FR2450257A1/fr active Granted
- 1980-02-28 DE DE19803007556 patent/DE3007556A1/de not_active Withdrawn
- 1980-02-28 SE SE8001556A patent/SE8001556L/xx not_active Application Discontinuation
- 1980-02-28 AR AR280125A patent/AR222375A1/es active
- 1980-02-29 BE BE0/199617A patent/BE882010A/fr not_active IP Right Cessation
- 1980-02-29 DK DK88880A patent/DK88880A/da not_active Application Discontinuation
- 1980-02-29 CH CH164080A patent/CH645109A5/de not_active IP Right Cessation
- 1980-02-29 AT AT0113780A patent/AT365409B/de not_active IP Right Cessation
- 1980-02-29 NL NL8001243A patent/NL8001243A/nl not_active Application Discontinuation
- 1980-02-29 GB GB8006873A patent/GB2045754B/en not_active Expired
- 1980-03-03 JP JP2649880A patent/JPS55133381A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1127362B (it) | 1986-05-21 |
| GB2045754B (en) | 1983-03-30 |
| NZ192923A (en) | 1981-11-19 |
| GB2045754A (en) | 1980-11-05 |
| IT8048013A0 (it) | 1980-02-26 |
| AR222375A1 (es) | 1981-05-15 |
| IL59334A (en) | 1984-01-31 |
| NL8001243A (nl) | 1980-09-04 |
| AT365409B (de) | 1982-01-11 |
| BE882010A (fr) | 1980-06-16 |
| FR2450257A1 (fr) | 1980-09-26 |
| ZA80978B (en) | 1981-02-25 |
| CH645109A5 (de) | 1984-09-14 |
| DE3007556A1 (de) | 1980-09-11 |
| FR2450257B1 (enrdf_load_stackoverflow) | 1983-06-10 |
| DK88880A (da) | 1980-09-03 |
| BR8001161A (pt) | 1980-11-04 |
| ATA113780A (de) | 1981-06-15 |
| SE8001556L (sv) | 1980-09-03 |
| AU5537680A (en) | 1980-09-04 |
| AU531808B2 (en) | 1983-09-08 |
| JPS55133381A (en) | 1980-10-17 |
| IL59334A0 (en) | 1980-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |