EP0027111A4 - LEPIDOPTERICAL ISOTHIO UREA COMPOUNDS. - Google Patents
LEPIDOPTERICAL ISOTHIO UREA COMPOUNDS.Info
- Publication number
- EP0027111A4 EP0027111A4 EP19800900649 EP80900649A EP0027111A4 EP 0027111 A4 EP0027111 A4 EP 0027111A4 EP 19800900649 EP19800900649 EP 19800900649 EP 80900649 A EP80900649 A EP 80900649A EP 0027111 A4 EP0027111 A4 EP 0027111A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- group
- defined above
- phenyl
- substituents
- 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.)
- Withdrawn
Links
- 150000002541 isothioureas Chemical class 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 241000255777 Lepidoptera Species 0.000 claims abstract description 30
- 230000000694 effects Effects 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 73
- 125000001424 substituent group Chemical group 0.000 claims description 64
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 63
- 125000003342 alkenyl group Chemical group 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- -1 pyranylmethyl Chemical group 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 40
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 31
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 19
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 17
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000002785 azepinyl group Chemical group 0.000 claims description 14
- 150000007530 organic bases Chemical class 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000002757 morpholinyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 9
- 229910005948 SO2Cl Inorganic materials 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 8
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- NMBHWGPVFIFLSR-UHFFFAOYSA-N potassium thiohypochlorite Chemical compound ClS[K] NMBHWGPVFIFLSR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004001 thioalkyl group Chemical group 0.000 claims description 8
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 7
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims 7
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 6
- 231100001184 nonphytotoxic Toxicity 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000000962 organic group Chemical group 0.000 claims 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- 230000000885 phytotoxic effect Effects 0.000 abstract description 4
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 86
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 80
- 239000000047 product Substances 0.000 description 78
- 238000006243 chemical reaction Methods 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 39
- 238000002329 infrared spectrum Methods 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000007788 liquid Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 238000004458 analytical method Methods 0.000 description 32
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000012360 testing method Methods 0.000 description 27
- 229940073584 methylene chloride Drugs 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- PTRPXBZNOKRNOC-UHFFFAOYSA-N ethyl n,n'-diheptylcarbamimidothioate Chemical compound CCCCCCCNC(SCC)=NCCCCCCC PTRPXBZNOKRNOC-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000376 reactant Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 239000012948 isocyanate Substances 0.000 description 11
- 150000002513 isocyanates Chemical class 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000012216 screening Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- PIYNUZCGMLCXKJ-UHFFFAOYSA-N 1,4-dioxane-2,6-dione Chemical compound O=C1COCC(=O)O1 PIYNUZCGMLCXKJ-UHFFFAOYSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 241000567412 Estigmene acrea Species 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- 229940093475 2-ethoxyethanol Drugs 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- 244000207667 Rumex vesicarius Species 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- LJCQVTRXVLDFET-UHFFFAOYSA-N 1-carbamothioyl-1-phenylurea Chemical compound NC(=O)N(C(S)=N)C1=CC=CC=C1 LJCQVTRXVLDFET-UHFFFAOYSA-N 0.000 description 3
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 240000004244 Cucurbita moschata Species 0.000 description 3
- 235000009854 Cucurbita moschata Nutrition 0.000 description 3
- 235000009852 Cucurbita pepo Nutrition 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- 241000256244 Heliothis virescens Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 235000015422 Rumex crispus ssp. crispus Nutrition 0.000 description 3
- 235000015426 Rumex crispus ssp. fauriei Nutrition 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 241000255993 Trichoplusia ni Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 235000012343 cottonseed oil Nutrition 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000020354 squash Nutrition 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 2
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical group CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- HDAOPVXBYGHPGY-UHFFFAOYSA-N carbamoyl chloride;ethyl n,n'-diheptylcarbamimidothioate Chemical compound NC(Cl)=O.CCCCCCCNC(SCC)=NCCCCCCC HDAOPVXBYGHPGY-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- CYTZQPDGQAYVQF-UHFFFAOYSA-N ethyl n'-heptyl-n-phenylcarbamimidothioate Chemical compound CCCCCCCN=C(SCC)NC1=CC=CC=C1 CYTZQPDGQAYVQF-UHFFFAOYSA-N 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 230000009526 moderate injury Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 208000037974 severe injury Diseases 0.000 description 2
- 230000009528 severe injury Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KWGFMMAPDMTJHX-UHFFFAOYSA-N sulfonylthiourea Chemical compound SC(=N)N=S(=O)=O KWGFMMAPDMTJHX-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- LNQOARMFZBNCHR-UHFFFAOYSA-N (1,1,2,2-tetrachloro-2-fluoroethyl) thiohypochlorite Chemical compound FC(Cl)(Cl)C(Cl)(Cl)SCl LNQOARMFZBNCHR-UHFFFAOYSA-N 0.000 description 1
- NTNKNFHIAFDCSJ-UHFFFAOYSA-N (2-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC=C1SCl NTNKNFHIAFDCSJ-UHFFFAOYSA-N 0.000 description 1
- GKQXPTHQTXCXEV-UHFFFAOYSA-N (4-chlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1 GKQXPTHQTXCXEV-UHFFFAOYSA-N 0.000 description 1
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- QNKQBDZVEKZFBN-UHFFFAOYSA-N 1-isocyanato-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(N=C=O)C=C1 QNKQBDZVEKZFBN-UHFFFAOYSA-N 0.000 description 1
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- WXYAXKKXIGHXDS-UHFFFAOYSA-N 1-isothiocyanatohexane Chemical compound CCCCCCN=C=S WXYAXKKXIGHXDS-UHFFFAOYSA-N 0.000 description 1
- PQFOUIMVTGBFRN-UHFFFAOYSA-N 2-isocyanato-1-methyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N=C=O PQFOUIMVTGBFRN-UHFFFAOYSA-N 0.000 description 1
- RQKFYFNZSHWXAW-UHFFFAOYSA-N 3-chloro-p-toluidine Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
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- 101100467574 Mus musculus Mras gene Proteins 0.000 description 1
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- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 description 1
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- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 240000003768 Solanum lycopersicum Species 0.000 description 1
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- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
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- 230000003197 catalytic effect Effects 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
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- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
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- SMQKTGLJONJOHC-UHFFFAOYSA-N ethyl n,n'-bis(2-ethylhexyl)carbamimidothioate Chemical compound CCCCC(CC)CNC(SCC)=NCC(CC)CCCC SMQKTGLJONJOHC-UHFFFAOYSA-N 0.000 description 1
- ZTZOXXIQGQMCFX-UHFFFAOYSA-N ethyl n,n'-di(heptan-2-yl)carbamimidothioate Chemical compound CCCCCC(C)NC(SCC)=NC(C)CCCCC ZTZOXXIQGQMCFX-UHFFFAOYSA-N 0.000 description 1
- SPCOTPSZIDKQCA-UHFFFAOYSA-N ethyl n,n'-diheptyl-n-(2-nitrophenyl)sulfanylcarbamimidothioate Chemical compound CCCCCCCN=C(SCC)N(CCCCCCC)SC1=CC=CC=C1[N+]([O-])=O SPCOTPSZIDKQCA-UHFFFAOYSA-N 0.000 description 1
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- UHMOPIOGANXAFP-UHFFFAOYSA-N ethyl n,n'-diheptyl-n-(trichloromethylsulfanyl)carbamimidothioate Chemical compound CCCCCCCN=C(SCC)N(SC(Cl)(Cl)Cl)CCCCCCC UHMOPIOGANXAFP-UHFFFAOYSA-N 0.000 description 1
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- GTNIUCCABFRICE-UHFFFAOYSA-N ethyl n-(2-chloroethylcarbamoyl)-n,n'-diheptylcarbamimidothioate Chemical compound CCCCCCCN=C(SCC)N(C(=O)NCCCl)CCCCCCC GTNIUCCABFRICE-UHFFFAOYSA-N 0.000 description 1
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- DBXLPMKQEIPFBO-UHFFFAOYSA-N ethyl n-(tert-butylcarbamoyl)-n,n'-diheptylcarbamimidothioate Chemical compound CCCCCCCN=C(SCC)N(C(=O)NC(C)(C)C)CCCCCCC DBXLPMKQEIPFBO-UHFFFAOYSA-N 0.000 description 1
- MVGKNSFQAQUIOU-UHFFFAOYSA-N ethyl n-carbonochloridoyl-n,n'-diheptylcarbamimidothioate Chemical compound CCCCCCCN=C(SCC)N(C(Cl)=O)CCCCCCC MVGKNSFQAQUIOU-UHFFFAOYSA-N 0.000 description 1
- KAOIUQQXAWCOAE-UHFFFAOYSA-N ethyl n-heptan-2-yl-n'-heptylcarbamimidothioate Chemical compound CCCCCCCN=C(SCC)NC(C)CCCCC KAOIUQQXAWCOAE-UHFFFAOYSA-N 0.000 description 1
- VXGMLKKEGPTWQS-UHFFFAOYSA-N ethyl n-heptan-2-yl-n'-hexylcarbamimidothioate Chemical compound CCCCCCN=C(SCC)NC(C)CCCCC VXGMLKKEGPTWQS-UHFFFAOYSA-N 0.000 description 1
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- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- WDXNCFLKDIQIBU-UHFFFAOYSA-N propyl N,N'-diheptylcarbamimidothioate Chemical compound CCCCCCCNC(SCCC)=NCCCCCCC WDXNCFLKDIQIBU-UHFFFAOYSA-N 0.000 description 1
- WTVQPKGLKTXCIS-UHFFFAOYSA-N propyl n,n'-diheptyl-n-(phenylcarbamoyl)carbamimidothioate Chemical compound CCCCCCCN=C(SCCC)N(CCCCCCC)C(=O)NC1=CC=CC=C1 WTVQPKGLKTXCIS-UHFFFAOYSA-N 0.000 description 1
- YBDWLAVEKOWERX-UHFFFAOYSA-N propyl n-heptan-2-yl-n'-octylcarbamimidothioate Chemical compound CCCCCCCCNC(SCCC)=NC(C)CCCCC YBDWLAVEKOWERX-UHFFFAOYSA-N 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
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- VFIZBHJTOHUOEK-UHFFFAOYSA-N s-ethylisothiourea Chemical class CCSC(N)=N VFIZBHJTOHUOEK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- INDZTCRIYSRWOH-UHFFFAOYSA-N undec-10-enyl carbamimidothioate;hydroiodide Chemical compound I.NC(=N)SCCCCCCCCCC=C INDZTCRIYSRWOH-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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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
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/36—Isothioureas having sulfur atoms of isothiourea groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/40—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of thiourea or isothiourea groups further bound to other hetero atoms
- C07C335/42—Sulfonylthioureas; Sulfonylisothioureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
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- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07F9/02—Phosphorus compounds
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- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
Definitions
- Lepidoptericidal isothiuronium compounds have been disclosed in the prior art particularly those described in U.S. Patents 3,969,511 and 4,062,892 and have the formula
- the present invention is a novel group of compounds which may generally be described as certain isothioureas which are active lepidoptericides.
- Compounds of the present invention are represented by the generic formula
- R and R 1 are independently selected from the group consisting of:
- C 2 -C 10 alkyl preferably C 5 -C 9 alkyl, more preferably C 6 -C 8 alkyl,
- C 2 -C 10 alkoxyalkyl preferably C 5 -C 9 alkoxyalkyl, more preferably C 6 -C 8 alkoxyalkyl and phenyl and R and R 1 together contain from 12 to 22 carbon atoms;
- R 2 is selected from the group consisting of:
- C 1 -C 14 alkyl preferably C 1 -C 6 alkyl, more preferably C 1 -C 3 alkyl,
- n 1-10, preferably 1-5, more preferably 1-3, phenyl and phenethyl; wherein R 3 is selected from the group consisting of:
- C 1 -C 4 alkyl preferably C 1 -C 2 alkyl, alkylketoalkyl wherein the alkyl is
- R 1 is -OH, -NH 2 or
- R, R 1 and R 2 are as defined above,
- B is a basic cation, preferably an organic basic cation, more preferably an organic basic cation selected from the group consisting of
- R 4 is selected from the group consisting of:
- -C 1 -C 22 alkyl preferably C 1 -C 12 alkyl, more preferably C 1 -C 8 alkyl and most preferably C 1 -C 6 alkyl, hydroxyethyl, naphthyl, phenyl, substituted phenyl wherein the substituents are independently selected from the group of halogen, preferably chlorine, C 1 -C 5 alkyl, preferably C 1 -C 2 alkyl, C 1 -C 5 alkoxy, preferably C 1 -C 2 alkoxy, nitro, cyano and -CF 3 ,
- R, R 1 and R 2 are as defined above,
- R, R 1 and R 2 are as defined above,
- R, R 1 and R 2 are as defined above,
- R, R 1 and R 2 are as defined above,
- R, R 1 and R 2 are as defined above,
- R, R 1 and R 2 are as defined above,
- R, R 1 and R 2 are as defined above, wherein X is selected from the group consisting of: O,
- R 10 is selected from the group consisting of:
- R 11 is selected from the group consisting of: C 1 -C 4 alkyl,
- heterocyclic compounds preferably heterocyclic compounds selected from the group consisting of: azepinyl, morpholinyl, piperdinyl, C 1 -C 3 alkyl substituted piperdinyl, and
- polyalkoxyamidoalkyl wherein the polyalkoxy moiety contains from 3-6 repeating C 2 -C 3 alkoxy units and the amidoalkyl moiety contains from 4-12 carbon atoms,
- R 5 is selected from the group consisting of: hydrogen
- R 6 is selected from the group consisting of:
- R 7 is selected from the group consisting of:
- M is H or Cl
- -NH is selected from the group consisting of:
- C 1 -C 18 alkyl preferably C 1 -C 12 alkyl, more preferably C 1 -C 4 alkyl, hydrogen
- R 1 and R 2 are as defined above, wherein R 8 is selected from the group consisting of:
- the compounds of the present invention are derivatives of isothioureas containing one free hydrogen atom attached to nitrogen, that is, as shoxra by the following formula:
- isothioureas are well knoxm in the art. They are derived by the reaction of an isothiocyanate xtfith a primary amine to form a thiourea followed by the reaction with an alkyl halide to produce an isothiourea salt.
- An unreactive solvent such as ethanol can be used for both the formation of the thiourea and the alkylation step to form the isothiourea salt. Heat is usually used to speed both reactions.
- the preparation of the isothiourea salt is shown below:
- the compounds of this invention are prepared by reacting the base of an isothiourea with an isocyanate or acid chloride.
- the free base can either be prepared by neutralization of an isothiourea salt with a cold aqueous solution of atase such as dilute sodium hydroxide, extracting the free isothiourea with a water insoluble solvent such as hexane, benzene, toluene, etc., drying over a dehydrating agent such as magnesium sulfate, filtering and evaporation under vacuum.
- An alternative procedure is to dissolve the isothiourea salt in a non-reactive solvent such as benzene or toluene then add ing an equal molar amount of an isocyanate and the equivalent amount of a soluble tertiary base or an acid chloride and two equivalent amounts of a soluble tertiary base such as triethylamine, completing the reaction by stirring at ambient temperature for several hours or refluxing for a shorter period of time.
- a non-reactive solvent such as benzene or toluene
- An alternative method when using a base such as triethylamine is to treat the isothiourea salt in a solvent such as benzene in which triethylamine hydrohalide is almost totally insoluble, filtering off the triethylamine hydrohalid and treating the filtrate with the isocyanate or acid chloride, completing the reaction as discussed previously.
- Solvents suitable for the condensation of the isothiourea with an isocyanate or acid chloride are those which are unreactive to any of the reactants. These include hexane, benzene, toluene, tetrahydrofuran, dioxane, methylenechloride, diethylether, and the like.
- reaction temperatures are generally within the range of -20°C to 80°C and reaction times vary from 0.5 hours to 24 hours.
- the isothiourea precursors of the prior art discussed above can in general be prepared by the methods disclosed in U.S. Patents 3,969,511 and 4,062,892.
- These compounds are useful as lepidoptericides when used in a lepidoptericidally effective amount on insects of the order lepidoptera or their habitat or feedstuffs. Some of the compounds also show phytotoxic effects which could render them useful as herbicides as well as lepidoptericides if such efficacy was desired. In addition, some of these compounds show biocidal and/or fungicidal effects.
- lepidoptericidally effective amount is meant the amount of the herein disclosed lepidoptericidal compounds which when applied in any conventional manner to the habitat of the lepidoptera, the feedstuffs of lepidoptera, or the insects themselves, will “control” by killing or substantially injuring a significant portion of the lepidoptera.
- crops to be protected include forest trees such as oak and pine, fruit trees such as peach, apple and walnut, vegetables such as tomatoes, other crops such as tobacco, cotton, lettuce, corn and rice and any crop which lepidoptera feed upon.
- novel compounds of this present invention can be prepared from the above precursors by methods shown in the following examples. 1,3-Diheptyl-2-ethyl-3-(0,0-dimethyl phosphoro) isothiourea
- reaction mass was stirred at 0°C for 30 minutes. Then, a solution of 8.7 g (0.04 mole ) of 25 percent sodium methoxide in methanol xrith 25 ml of methylenechloride was added over a period of 15 minutes while the pot temperature was maintained at 0 to 5°C. The reaction mass was then stirred at 5°C for 30 minutes and then at room temperature for 30 minutes. The resulting mixture was then washed with two 200 ml portions of water and phase separated.
- the ether was washed with 100 ml of water, then dried and stripped to yield 2 g of the title product.
- the structure was verified by IR and NMR spectra.
- Example 12 The procedure was the same as for Example 10 except ethyl acrylate was replaced with methyl vinyl ketone and the reaction was run at room temperature for 4 hours. Work-up of the product was the same. 2 g of the title product was produced and identified by IR and NMR spectra. Compound No. 200 in Table I.
- Example 12 The procedure was the same as for Example 10 except ethyl acrylate was replaced with methyl vinyl ketone and the reaction was run at room temperature for 4 hours. Work-up of the product was the same. 2 g of the title product was produced and identified by IR and NMR spectra. Compound No. 200 in Table I. Example 12
- Example 13 The procedure for Example 13 is the same as for Example 12 above with the exception that a 200 ml single necked round bottom flask was used in place of the 100 ml flask and 1.16 g (9.13 millimoles) of oxalyl chloride was substituted for the ethyloxalyl chloride of the previous example.
- the reaction resulted in a clear yellow solution which was stirred at 0°C for 1 hour and then stirred at room temperature for 20 hours.
- the clear yellow solution was then transferred to a separatory funnel containing 50 ml of water and 50 ml of methylene chloride.
- N,N'-Pi-(1-heptyl)-N'-(ethylmercapto carbonyl)-S-ethyl isothiourea The procedure and equipment were the same as in Example 12 above with the exception that 5.0 g (16.6 millimoles) of N,N'-di-(1-heptyl)-S-ethyl isothiourea and 1.85 g (18.3 millimoles) of triethylamine and 50 ml of methylene chlorde were added to the flask followed by addition of 2.28 g (18.3 millimoles) of ethylthio chloroformate. The resultant product was phase separated, washed and dried in a manner of Example 12.
- Step b) Preparation of 1,3-diheptyl-2-ethyl-3-[3'-(2'' ethoxyethoxycarbonylamino)-4'-methylphenylaminocarbonyl] isothiourea.
- Step a) Preparation of 1-octyl-2-ethyl-3-sec-heptyl-3-(3-isocyanato-4-methylphenylaminocarbonyl) isothiourea (Intermediate).
- This intermediate was prepared as was the intermediate of Example 15 a) with the exception that 27.2 g (0.086 mole) of 1-octyl-2-ethyl-3-sec-heptyl- isothiourea was substituted for the thiourea reactant of step 25 a).
- the reaction produced 41.5 g (98.8 weight percent of theory) of a liquid having a n D 30 of 1.5280 which identified as the title intermediate by IR and carbon 13 NMR spectra analyses,
- Step b) Preparation of 1-octyl-2-ethyl-3-sec-heptyl-3- [3-(1-octyl-2-propyl-3-sec-heptyl-3-carbonylamino)-4-methylphenylcarbonylamino] isothiourea.
- step 15 b The title product was prepared in the manner of step 15 b) with the exception of using 4.87 g (0.010 mole) of the intermediate prepared in step 20 a) and 3.29 g (0.010 mole) of 1-octyl-2-propyl-3-sec-heptyl isothiourea.
- the isothiuronium salt was dissolved in 200 ml of toluene and washed with 100 cc of 5 percent sodium hydroxide. The toluene layer was then washed twice with 150 cc portions of water, dried over magnesium sulfate, filtered and vacuum evaporated. The product was then stripped under high vacuum to produce 7.78 g (92.6 weight percent of theory yield) of a clear, yellow liquid having a n D 30 of 1.4768. The product was identified as the title product by IR and NMR spectra analyses.
- Example 26 The procedure and equipment were the same as in Example 26. 1.9 g (0.006 mole) 1-sec-heptyl-3-n-octyl-2-S-allyl isothiourea was mixed with 25 ml of tetrahydrofuran to which 1.77 g (0.006 mole) n-octadecylisocyanate was added to the mixture. The reaction mixture was then stirred at ambient temperature overnight and then vacuum evaporated to produce 3.79 g (100 weight percent of theory yield) of a clear liquid hiving a n D 30 of 1.4769. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 144 in Table I.
- Example 41 The equipment was the same as in Example 41. 3.0 g (0.01 mole) of 1,3-di-n-heptyl-2-S-ethyl isothiourea dissolved in 15 ml glycol and 1.2 g (0.01 mole) diglycolic anhydride dissolved in 10 ml glycol were added thereto. The reaction was heated to reflux for 10 minutes and evaporated under vacuum to produce 4.1 g of a liquid having a n D 30 of 1.4608. The product was identified as the title product by IR and NMR spectra analyses. Compound No. 321 in Table I.
- Lepidoptericidal activity of the above compounds were evaluated for efficacy on various lepidopterous species as follows:
- a test solution is prepared by dissolving the test compound in a 50-50 acetone-water solution.
- a section of a curly dock (Rumex crispus) leaf is immersed in the test solution for 2-3 seconds, then placed on a wire screen to dry.
- the dried leaf is placed in a petri dish containing a moistened piece of filter paper, and infested with 5 second-instar salt-marsh caterpillar larvae. Mortality of the larvae is recorded 48 hours later. If surviving larvae are still present, a piece of synthetic media is added to the dish and the larvae are observed for an additional 5 days in order to detect delayed effects of the test compound.
- the primary screening level for this test is 0.05 percent by weight of the test compound in the solution.
- Larvae of the tobacco budworm are used in this test in a procedure identical to that used for saltmarsh caterpillar larvae, except that a Romaine lettuce (Latuca sativa) leaf section of approximately the same size as the curly dock leaf section is used in place of the latter.
- the primary screening level for this test is 0.1 percent by weight of the test compound in the solution.
- Table II summarizes the results of the lepidoptericidai tests performed on the compounds of Table I. These test results are expressed as LD 50 values, which represent the dose of test compound which was lethal to 50 percent of the insect population in the test.
- the entries in Table II were obtained as follows:
- each compound was initially tested at the primary screening level. Those compounds showing less than 50 percent kill at this level are represented in the table by the primary screening level preceded by a "greater than” sign ( > ). Those compounds showing approximately 50 percent kill are represented by the primary screening level alone. Those compounds showing greater than 50 percent kill were subjected to further testing at successively lower levels, until the level was found at which approximately 50 percent kill was achieved. The latter level is listed as the LD 50 for this group.
- Phytotoxicity tests are conducted on cotton (Gossaypium hirsutum) and hyzini squash (Calabacita abobrinha) seedlings. Plants are grown and treated in Kaiser No. 1059 6" ⁇ 9" ⁇ 3" aluminum flats. Each flat contains one row of cotton and one row of squash, with 6-8 plants per row. The plants are grown in the greenhouse and are treated when they are approximately 8 days old and 2" tall.
- test compounds are diluted in a 50-50 acetone-water solution and formulated compounds are diluted in water. These test solutions are then sprayed on the flats in a Ducon-Savko Model 3400 linear spray table atrates of 1/2, 1, 2, and 4 lbs a.i./80 gallons/acre. The treated plants are then placed in the greenhouse and watered in such a way that the foliage is not wet.
- Table II also summarizes the results of the phytotoxicity tests performed on the compounds of Table I.
- the primary screening level in each of the above tests was selected for purposes of convenience only, and none of the figures in the table are to be understood as representing the highest level at which a viable test for lepidoptericidal activity can be conducted.
- Tubes of sterilized nutrient and malt extract broth were prepared. Aliquots of the toxicant, dissolved in an appropriate solvent, were injected through the stopper, into the broth, to provide concentrations ranging from 50 ppm downward.
- the test organisms consisted of one fungi, Botrytus cinerea, and one bacteria, Staphylococcus aureus (S.a.) Roseenbach.
- Bean Powdery Mildew - - The chemicals were dissolved in an appropriate solvent and diluted with water containing several drops of a wetting agent. Test concentrations, ranging from 1000 ppm downward, were sprayed to runoff on the primary leaves of pinto beans (Phaseolus vulgaris L.). After the plants were dry, the leaves were dusted with spores of the powdery mildew fungus (Erysiphe polygoni de Candolle) and the plants were retained in the greenhouse until the fungal growth appeared on the leaf surface. Effectiveness was recorded as the lowest concentration, in ppm, which will provide 75 percent or greater reduction in mycelial growth on the leaf surface as compared to untreated, inoculated plants. The results are shown in Table III.
- the primary screening level in each of the above tests was selected for purposes of convenience only, and none of the figures in the table are to be understood as representing the highest level at which a viable test for lepidoptericidai activity can be conducted.
- the compounds of this invention are generally used in formulations suitable for convenient application.
- such formulations will contain inert or other active ingredients or diluent carriers in addition to the active compound.
- ingredients or carriers are organic solvents, such as sesame oil, xylene range solvents, and heavy petroleum; water; emulsifying agents; surface active agents; talc; pyrophyllite; diatomite; gypsum; clays; and propellants, such as dichlorodifluoromethane.
- the active compounds can further be combined with dust carriers for application as dusts, with granular carriers for application by fertilizer spreaders or ground or airplane seeders. It also can be formulated as a wettable powder or a flowable for application as a water suspension, or with solvents and surface active materials for application as sprays, aerosols, or emulsions.
- the compounds or their formulated mixtures can be applied to any habitat of the pests. Examples of such habitats are insect dwellings, clothing, plant surfaces, and soil.
- the active compositions can be applied directly to organic matter, seeds or feedstuffs in general, upon which the pests feed, or directly to the pests themselves. When applied in such a manner, it will be advantageous to use a formulation which is not volatile.
- compositions are those comprising an insecticidally effective amount of the active compound in combination with an inert insoluble solid carrier vehicle.
- examples of such compositions are wettable powders, dusts, and flowable formulations, in which the solid carrier is in finely divided form; and granular formulations, in which the solid carrier is a pre-formed granule.
- isothiourea compounds can also be formulated to include baits that induce feeding responses in the lepidoptera larva resulting in earlier ingestion of the lepidoptericidai isothioureas.
- Effective baits include cottonseed flour, cottonseed oil, extract of mature cottonseed, sucrose, invert sugar, citrus molasses, soybean oil, soy flour, corn oil, extract of corn kernels, extract of corn silks, extract of corn seed and mixtures thereof together with suitable emulsifiers and wetting agents.
- the amount of active compound or formulation which is considered to be insecticidally effective is that amount which, when applied to the pest habitat or feedstuff, will kill or substantially injure a significant portion residing or feeding thereon.
- the active compounds of this invention can be employed either as the sole pesticide component of the formulations or as one of a mixture of compounds in the formulation having similar utility.
- the presentl disclosed pesticide compositions need not be active as such.
- the purposes of this invention will be fully served by a composition which is rendered active by external influences, such as light, or by physiological action occurring when the preparation is ingested or penetrates into the body of the pest.
- the active pesticidal compound will be used as a component of a liquid composition; for example, an emulsion, suspension, or aerosol spray. While the concentration of the active pesticide compound in the present formulation can vary within rather wide limits, ordinarily, the pesticide composition will comprise not more than about 50.0 percent by weight of the formulation.
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2136879A | 1979-03-19 | 1979-03-19 | |
US21368 | 1993-02-23 |
Publications (2)
Publication Number | Publication Date |
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EP0027111A1 EP0027111A1 (en) | 1981-04-22 |
EP0027111A4 true EP0027111A4 (en) | 1982-04-08 |
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Application Number | Title | Priority Date | Filing Date |
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EP19800900649 Withdrawn EP0027111A4 (en) | 1979-03-19 | 1980-10-08 | LEPIDOPTERICAL ISOTHIO UREA COMPOUNDS. |
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EP (1) | EP0027111A4 (xx) |
JP (1) | JPS56500139A (xx) |
KR (1) | KR830001611A (xx) |
AU (1) | AU5653580A (xx) |
BE (1) | BE882296A (xx) |
BR (1) | BR8007864A (xx) |
CA (1) | CA1138883A (xx) |
DD (1) | DD149454A5 (xx) |
DK (1) | DK491880A (xx) |
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FI (1) | FI800840A (xx) |
IL (1) | IL59618A0 (xx) |
IN (1) | IN151825B (xx) |
IT (1) | IT8048199A0 (xx) |
MA (1) | MA18770A1 (xx) |
NO (1) | NO803467L (xx) |
NZ (1) | NZ193159A (xx) |
PL (1) | PL122648B1 (xx) |
PT (1) | PT70974A (xx) |
TR (1) | TR20681A (xx) |
WO (1) | WO1980002024A1 (xx) |
YU (1) | YU76080A (xx) |
ZA (1) | ZA801572B (xx) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3136891A1 (de) * | 1981-09-17 | 1983-03-31 | Basf Ag, 6700 Ludwigshafen | Neue isothioharnstoffe, ihre herstellung, ihre verwendung zur unkrautbekaempfung und mittel dafuer |
WO1984002650A1 (en) * | 1983-01-05 | 1984-07-19 | Us Agriculture | A method for the control of insects |
US4537620A (en) * | 1984-07-02 | 1985-08-27 | Stauffer Chemical Company | Aryloxyphenoxy proponyl isothioureas and use as herbicides |
US4613356A (en) * | 1984-08-06 | 1986-09-23 | Stauffer Chemical Company | Aryloxyphenoxy propionylthioureas which are useful as herbicides |
US4714493A (en) * | 1985-05-24 | 1987-12-22 | Stauffer Chemical Company | Isothiourea herbicidal composition |
US9206381B2 (en) | 2011-09-21 | 2015-12-08 | Ecolab Usa Inc. | Reduced misting alkaline cleaners using elongational viscosity modifiers |
US9637708B2 (en) | 2014-02-14 | 2017-05-02 | Ecolab Usa Inc. | Reduced misting and clinging chlorine-based hard surface cleaner |
TWI677491B (zh) * | 2014-08-26 | 2019-11-21 | 美商陶氏農業科學公司 | 具有一定殺蟲效用之分子,及與其相關之中間物、組成物暨方法 |
EP3464542B1 (en) | 2016-05-23 | 2020-04-29 | Ecolab USA Inc. | Reduced misting acidic cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight water-in-oil emulsion polymers |
ES2808999T3 (es) | 2016-05-23 | 2021-03-02 | Ecolab Usa Inc | Composiciones de limpieza antisépticas y desinfectantes alcalinas y neutras con reducción de la formación de neblina a través del uso de polímeros de emulsión de agua en aceite de alto peso molecular |
AU2018227539B2 (en) | 2017-03-01 | 2020-04-09 | Ecolab Usa Inc. | Reduced inhalation hazard sanitizers and disinfectants via high molecular weight polymers |
JP2022540474A (ja) | 2019-07-12 | 2022-09-15 | エコラボ ユーエスエー インコーポレイティド | アルカリ可溶性エマルジョンポリマーの使用によりミストが低減したアルカリ性洗浄剤 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1667053A (en) * | 1925-07-16 | 1928-04-24 | Firm Chem Fab Auf Actien | Diacyl isothiocarbamide ether and method of producing same |
US3969511A (en) * | 1974-03-29 | 1976-07-13 | Stauffer Chemical Company | Insecticidal, miticidal and lepidoptericidal active isothiuronium complex acids and free bases |
US4062892A (en) * | 1976-09-13 | 1977-12-13 | Stauffer Chemical Company | Insecticidal, miticidal and lepidoptericidal active isothiuronium complex acids and free bases |
-
1980
- 1980-01-21 JP JP50078180A patent/JPS56500139A/ja active Pending
- 1980-01-21 WO PCT/US1980/000110 patent/WO1980002024A1/en not_active Application Discontinuation
- 1980-01-21 BR BR8007864A patent/BR8007864A/pt unknown
- 1980-03-10 MA MA18968A patent/MA18770A1/fr unknown
- 1980-03-13 NZ NZ193159A patent/NZ193159A/xx unknown
- 1980-03-14 IL IL59618A patent/IL59618A0/xx unknown
- 1980-03-18 FI FI800840A patent/FI800840A/fi not_active Application Discontinuation
- 1980-03-18 PL PL1980222792A patent/PL122648B1/pl unknown
- 1980-03-18 IT IT8048199A patent/IT8048199A0/it unknown
- 1980-03-18 TR TR20681A patent/TR20681A/xx unknown
- 1980-03-18 ES ES489689A patent/ES8103036A1/es not_active Expired
- 1980-03-18 DD DD80219743A patent/DD149454A5/de unknown
- 1980-03-18 KR KR1019800001130A patent/KR830001611A/ko unknown
- 1980-03-18 CA CA000347888A patent/CA1138883A/en not_active Expired
- 1980-03-18 AU AU56535/80A patent/AU5653580A/en not_active Abandoned
- 1980-03-19 PT PT70974A patent/PT70974A/pt unknown
- 1980-03-19 YU YU00760/80A patent/YU76080A/xx unknown
- 1980-03-19 IN IN316/CAL/80A patent/IN151825B/en unknown
- 1980-03-19 BE BE2/58464A patent/BE882296A/fr not_active IP Right Cessation
- 1980-08-18 ZA ZA00801572A patent/ZA801572B/xx unknown
- 1980-10-08 EP EP19800900649 patent/EP0027111A4/en not_active Withdrawn
- 1980-11-18 NO NO803467A patent/NO803467L/no unknown
- 1980-11-19 DK DK491880A patent/DK491880A/da not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
ES489689A0 (es) | 1981-02-16 |
WO1980002024A1 (en) | 1980-10-02 |
FI800840A (fi) | 1980-09-20 |
ZA801572B (en) | 1981-08-26 |
CA1138883A (en) | 1983-01-04 |
BR8007864A (pt) | 1981-02-03 |
AU5653580A (en) | 1980-09-25 |
BE882296A (fr) | 1980-09-19 |
ES8103036A1 (es) | 1981-02-16 |
PL222792A1 (xx) | 1980-12-15 |
MA18770A1 (fr) | 1980-10-01 |
NZ193159A (en) | 1983-06-14 |
IT8048199A0 (it) | 1980-03-18 |
KR830001611A (ko) | 1983-05-18 |
NO803467L (no) | 1980-11-18 |
JPS56500139A (xx) | 1981-02-12 |
DD149454A5 (de) | 1981-07-15 |
TR20681A (tr) | 1982-04-28 |
EP0027111A1 (en) | 1981-04-22 |
DK491880A (da) | 1980-11-19 |
IL59618A0 (en) | 1980-06-30 |
PT70974A (en) | 1980-04-01 |
PL122648B1 (en) | 1982-08-31 |
IN151825B (xx) | 1983-08-13 |
YU76080A (en) | 1983-04-30 |
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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Inventor name: SCHER, HERBERT B. Inventor name: FANCHER, LLEWELLYN W. |