CH512188A - Ubergangsmetallkomplexe von substituierten 2-Benzimidazolcarbamidsäurealkylestern enthaltende Schädlingsbekämpfungsmittel - Google Patents

Ubergangsmetallkomplexe von substituierten 2-Benzimidazolcarbamidsäurealkylestern enthaltende Schädlingsbekämpfungsmittel

Info

Publication number: CH512188A
Authority: CH; Switzerland
Prior art keywords: benzimidazole; complex; methyl ester; carbon atoms; dihydrate
Prior art date: 1968-04-12

Application number

CH545369A

Other languages

German (de)

English (en)

Inventor

Louis Klopping Hein

Original Assignee

Du Pont

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1968-04-12

Filing date

1969-04-10

Publication date

1971-09-15

1969-04-10 Application filed by Du Pont filed Critical Du Pont

1971-09-15 Publication of CH512188A publication Critical patent/CH512188A/de

Links

-1 2-benzimidazole carbamate transition metal Chemical class 0.000 title claims abstract description 208
229910052723 transition metal Inorganic materials 0.000 title abstract description 6
239000000417 fungicide Substances 0.000 title description 7
229910052725 zinc Inorganic materials 0.000 claims abstract description 126
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 68
229910052748 manganese Inorganic materials 0.000 claims abstract description 39
125000000217 alkyl group Chemical group 0.000 claims abstract description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 17
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
229910052759 nickel Inorganic materials 0.000 claims abstract description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
229910052742 iron Inorganic materials 0.000 claims abstract description 8
229910052802 copper Inorganic materials 0.000 claims abstract description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 7
229910052793 cadmium Inorganic materials 0.000 claims abstract description 6
229910052804 chromium Inorganic materials 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
150000004683 dihydrates Chemical class 0.000 claims description 138
239000011701 zinc Substances 0.000 claims description 128
239000000203 mixture Substances 0.000 claims description 79
239000002253 acid Substances 0.000 claims description 73
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 72
125000004432 carbon atom Chemical group C* 0.000 claims description 67
241000196324 Embryophyta Species 0.000 claims description 64
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 56
239000011572 manganese Substances 0.000 claims description 37
238000000034 method Methods 0.000 claims description 37
150000004702 methyl esters Chemical class 0.000 claims description 35
238000002360 preparation method Methods 0.000 claims description 34
235000013399 edible fruits Nutrition 0.000 claims description 33
239000004480 active ingredient Substances 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 29
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241000233866 Fungi Species 0.000 claims description 27
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 26
239000000575 pesticide Substances 0.000 claims description 24
238000011282 treatment Methods 0.000 claims description 24
241000221785 Erysiphales Species 0.000 claims description 23
239000007787 solid Substances 0.000 claims description 21
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RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical group C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 claims description 19
150000004682 monohydrates Chemical class 0.000 claims description 19
BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical compound NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 claims description 17
235000011430 Malus pumila Nutrition 0.000 claims description 17
235000015103 Malus silvestris Nutrition 0.000 claims description 17
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 17
239000000243 solution Substances 0.000 claims description 17
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 14
230000008569 process Effects 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
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125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
239000003921 oil Substances 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
239000007921 spray Substances 0.000 claims description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
239000012071 phase Substances 0.000 claims description 11
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 9
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239000010949 copper Substances 0.000 claims description 6
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 6
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
239000011651 chromium Substances 0.000 claims description 5
229910017052 cobalt Inorganic materials 0.000 claims description 5
239000010941 cobalt Substances 0.000 claims description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
150000003871 sulfonates Chemical class 0.000 claims description 5
241000219094 Vitaceae Species 0.000 claims description 4
241000607479 Yersinia pestis Species 0.000 claims description 4
229940072049 amyl acetate Drugs 0.000 claims description 4
ZFDLFHQAGYPRBY-UHFFFAOYSA-N chloro acetate Chemical group CC(=O)OCl ZFDLFHQAGYPRBY-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
235000021021 grapes Nutrition 0.000 claims description 4
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 4
239000004753 textile Substances 0.000 claims description 4
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
241000239290 Araneae Species 0.000 claims description 3
230000001419 dependent effect Effects 0.000 claims description 3
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239000011737 fluorine Chemical group 0.000 claims description 3
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239000000377 silicon dioxide Substances 0.000 claims description 3
239000007790 solid phase Substances 0.000 claims description 3
239000000454 talc Substances 0.000 claims description 3
229910052623 talc Inorganic materials 0.000 claims description 3
230000003442 weekly effect Effects 0.000 claims description 3
239000012141 concentrate Substances 0.000 claims description 2
239000002480 mineral oil Substances 0.000 claims description 2
235000010446 mineral oil Nutrition 0.000 claims description 2
239000004533 oil dispersion Substances 0.000 claims description 2
239000012074 organic phase Substances 0.000 claims description 2
229940072033 potash Drugs 0.000 claims description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
235000015320 potassium carbonate Nutrition 0.000 claims description 2
230000003449 preventive effect Effects 0.000 claims description 2
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241000220225 Malus Species 0.000 claims 2
244000141359 Malus pumila Species 0.000 claims 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
229910002651 NO3 Inorganic materials 0.000 claims 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
229940071125 manganese acetate Drugs 0.000 claims 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
230000000855 fungicidal effect Effects 0.000 abstract description 11
208000031888 Mycoses Diseases 0.000 abstract description 5
150000003624 transition metals Chemical class 0.000 abstract description 3
230000003151 ovacidal effect Effects 0.000 abstract description 2
UEZYAFPJFMPLBS-UHFFFAOYSA-N (2-aminobenzimidazol-2-yl)carbamic acid Chemical class C1=CC=CC2=NC(N)(NC(O)=O)N=C21 UEZYAFPJFMPLBS-UHFFFAOYSA-N 0.000 abstract 1
241000239223 Arachnida Species 0.000 abstract 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
239000000047 product Substances 0.000 description 50
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
239000008187 granular material Substances 0.000 description 28
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 25
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150000003839 salts Chemical class 0.000 description 21
238000003756 stirring Methods 0.000 description 21
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238000002329 infrared spectrum Methods 0.000 description 13
235000019198 oils Nutrition 0.000 description 12
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 11
238000004458 analytical method Methods 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
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UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 description 8
240000007594 Oryza sativa Species 0.000 description 8
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UWRBYRMOUPAKLM-UHFFFAOYSA-L lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
125000005524 levulinyl group Chemical group 0.000 description 1
229960002809 lindane Drugs 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
229960000453 malathion Drugs 0.000 description 1
150000002696 manganese Chemical class 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
JUTXSMADXIHOTO-UHFFFAOYSA-N methyl n-(1-acetylbenzimidazol-2-yl)carbamate Chemical compound C1=CC=C2N(C(C)=O)C(NC(=O)OC)=NC2=C1 JUTXSMADXIHOTO-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000003129 miticidal effect Effects 0.000 description 1
LQBJJHHESGHBDW-UHFFFAOYSA-N n-(1,3-dithiolan-2-ylidene)hydroxylamine Chemical compound ON=C1SCCS1 LQBJJHHESGHBDW-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
229940078487 nickel acetate tetrahydrate Drugs 0.000 description 1
OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical group CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
235000021017 pears Nutrition 0.000 description 1
LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940096826 phenylmercuric acetate Drugs 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002367 phosphate rock Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
230000029553 photosynthesis Effects 0.000 description 1
238000010672 photosynthesis Methods 0.000 description 1
230000000243 photosynthetic effect Effects 0.000 description 1
235000021018 plums Nutrition 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229940051841 polyoxyethylene ether Drugs 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
235000015136 pumpkin Nutrition 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
210000000614 rib Anatomy 0.000 description 1
JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 1
JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RCIJACVHOIKRAP-UHFFFAOYSA-N sodium;1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound [Na+].CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC RCIJACVHOIKRAP-UHFFFAOYSA-N 0.000 description 1
UMEWSJNRBXKWKZ-UHFFFAOYSA-M sodium;1,4-dioxo-1,4-dipentoxybutane-2-sulfonate Chemical compound [Na+].CCCCCOC(=O)CC(S([O-])(=O)=O)C(=O)OCCCCC UMEWSJNRBXKWKZ-UHFFFAOYSA-M 0.000 description 1
IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
AUPJTDWZPFFCCP-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCN(C)CCS([O-])(=O)=O AUPJTDWZPFFCCP-GMFCBQQYSA-M 0.000 description 1
HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000600 sorbitol Chemical class 0.000 description 1
238000009331 sowing Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
229940104261 taurate Drugs 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Chemical class 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH545369A 1968-04-12 1969-04-10 Ubergangsmetallkomplexe von substituierten 2-Benzimidazolcarbamidsäurealkylestern enthaltende Schädlingsbekämpfungsmittel CH512188A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US72106168A	1968-04-12	1968-04-12
US80471069A	1969-03-05	1969-03-05

Publications (1)

Publication Number	Publication Date
CH512188A true CH512188A (de)	1971-09-15

Family

ID=27110360

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH545369A CH512188A (de)	1968-04-12	1969-04-10	Ubergangsmetallkomplexe von substituierten 2-Benzimidazolcarbamidsäurealkylestern enthaltende Schädlingsbekämpfungsmittel

Country Status (6)

Country	Link
BE (1)	BE731234A (da)
CH (1)	CH512188A (da)
DK (1)	DK129995B (da)
IE (1)	IE32676B1 (da)
LU (1)	LU58386A1 (da)
SE (1)	SE368402B (da)

1969
- 1969-03-20 IE IE37169A patent/IE32676B1/xx unknown
- 1969-04-08 LU LU58386D patent/LU58386A1/xx unknown
- 1969-04-09 BE BE731234D patent/BE731234A/xx unknown
- 1969-04-10 SE SE506569A patent/SE368402B/xx unknown
- 1969-04-10 CH CH545369A patent/CH512188A/de not_active IP Right Cessation
- 1969-04-11 DK DK202469A patent/DK129995B/da unknown

Also Published As

Publication number	Publication date
IE32676B1 (en)	1973-10-31
DK129995B (da)	1974-12-09
BE731234A (da)	1969-09-15
DK129995C (da)	1975-05-20
SE368402B (da)	1974-07-01
LU58386A1 (da)	1969-07-18
IE32676L (en)	1969-10-12

Legal Events

Date	Code	Title	Description
1980-02-15	PL	Patent ceased

Publication	Publication Date	Title
US3631176A (en)	1971-12-28	Carbamoyl substituted 2-aminobenzimidazoles
NO168008B (no)	1991-09-23	En likestroemselektromagnet, spesielt for en elektrisk bryteranordning.
DE1620175A1 (de)	1970-05-21	Fungicides Mittel
EP0183217B1 (de)	1990-06-13	Mikrobizide Mittel
EP0158954A2 (de)	1985-10-23	Tetrahydrochinolin-1-ylcarbonylimidazol-Derivate, Zwischenprodukte für diese, Verfahren zur ihrer Herstellung und Herbizide oder Fungizide für Landwirtschaft und Gartenbau
US3836569A (en)	1974-09-17	Alkyl 4-(o-(substituted methyleneamino)phenyl)-3-thioallophanates
US3427388A (en)	1969-02-11	Esters of benzimidazolecarbamic acid as mite ovicides
US3958007A (en)	1976-05-18	Pesticidal alkyl 4-(0-(substituted methyleneamine)-phenyl)-3-thioallophanates
US3641048A (en)	1972-02-08	Alkyl 1 - (substituted alkylideneaminooxycarbonyl) - 2 -benzimidazolecarbamates
US3562282A (en)	1971-02-09	Transition metal complexes of substituted 2 -benzimidazolecarbamic acid,alkyl esters and their preparation
US3662069A (en)	1972-05-09	Alkyl 1-(n-substituted thiocarbamoyl)-2-benzimidazolecarbamates as fungicides and mite ovicides
US3636005A (en)	1972-01-18	Acyl substituted 2-benzimidazolecarbamates
US4018926A (en)	1977-04-19	Alkyl 4-[o-(substituted methyleneamino)-phenyl]-3-thioallophanate miticides and fungicides
US3789122A (en)	1974-01-29	Fungicidal compositions of transition metal complexes of substituted 2-benzimidazolecarbamic acid, alkyl esters
DE1917360A1 (de)	1969-10-23	UEbergangsmetallkomplexe von substituierten 2-Benzimidazolcarbamidsaeurealkylestern
CH512188A (de)	1971-09-15	Ubergangsmetallkomplexe von substituierten 2-Benzimidazolcarbamidsäurealkylestern enthaltende Schädlingsbekämpfungsmittel
CH499265A (de)	1970-11-30	Milbenovicid und Fungicid bzw. gegen Milben und Fungi geschütztes nichttextiles Material
CH663021A5 (de)	1987-11-13	Thiocyanopyrimidin-derivat, verfahren zur herstellung desselben und dasselbe als wirksames ingrediens enthaltendes land- und gartenwirtschaftliches fungizid.
DE2504052A1 (de)	1975-08-14	Neue wasserloesliche imidazol-derivate
US3655657A (en)	1972-04-11	2 1 4-benzothiadiazine-3-carbamic acid esters
US3595870A (en)	1971-07-27	Metal complexes of 2-benzimidazolecarbamic acid esters
US3950391A (en)	1976-04-13	Alkyl 4-(o-aminophenyl)-3-thioallophanates
US3927069A (en)	1975-12-16	Alkyl 4-{8 o-(substituted amino)phenyl{9 -3-thioallophanates
US4010278A (en)	1977-03-01	Compositions of alkyl 4-[o-(substituted amino)phenyl]-3-thioallophanates and methods of use
US4011213A (en)	1977-03-08	Alkyl 4-[o-(substituted methyleneamino)phenyl]-3-thioallophanates