NO127152B

NO127152B -

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Info

Publication number: NO127152B
Authority: NO; Norway
Prior art keywords: complex; acid; methyl ester; manganese; zinc
Prior art date: 1968-04-12

Application number

NO01152/69A

Other languages

English (en)

Norwegian (no)

Inventor

Hein Louis Klopping

Original Assignee

Du Pont

Priority date

1968-04-12

Filing date

1969-03-20

Publication date

1973-05-14

1969-03-20 Application filed by Du Pont filed Critical Du Pont

1973-05-14 Publication of NO127152B publication Critical patent/NO127152B/no

Links

150000001875 compounds Chemical class 0.000 claims description 117
150000004683 dihydrates Chemical class 0.000 claims description 41
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 27
229910052725 zinc Inorganic materials 0.000 claims description 27
239000011701 zinc Substances 0.000 claims description 26
JYBGVFYNRAPJRJ-UHFFFAOYSA-N [1-(butylcarbamoyl)benzimidazol-2-yl]carbamic acid Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(O)=O)=NC2=C1 JYBGVFYNRAPJRJ-UHFFFAOYSA-N 0.000 claims description 25
229910052748 manganese Inorganic materials 0.000 claims description 25
239000011572 manganese Substances 0.000 claims description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 17
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
150000004682 monohydrates Chemical class 0.000 claims description 14
239000007787 solid Substances 0.000 claims description 13
230000000855 fungicidal effect Effects 0.000 claims description 11
WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 claims description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
229910052759 nickel Inorganic materials 0.000 claims description 9
239000002002 slurry Substances 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 8
229910052742 iron Inorganic materials 0.000 claims description 7
BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical compound NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 claims description 6
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
230000009471 action Effects 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
229910052793 cadmium Inorganic materials 0.000 claims description 6
229910052804 chromium Inorganic materials 0.000 claims description 6
239000011651 chromium Substances 0.000 claims description 6
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 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
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 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
229910002651 NO3 Inorganic materials 0.000 claims description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
229910021653 sulphate ion Inorganic materials 0.000 claims description 2
241000223290 Hypherpes complex Species 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
239000011702 manganese sulphate Substances 0.000 claims 1
235000007079 manganese sulphate Nutrition 0.000 claims 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 claims 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims 1
239000011686 zinc sulphate Substances 0.000 claims 1
235000009529 zinc sulphate Nutrition 0.000 claims 1
-1 1-(o-methoxybenzylcarbamoyl)-2-benzimidazolecarbamic acid Chemical compound 0.000 description 67
241000196324 Embryophyta Species 0.000 description 64
239000000203 mixture Substances 0.000 description 57
150000004702 methyl esters Chemical class 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
235000013339 cereals Nutrition 0.000 description 37
239000000047 product Substances 0.000 description 32
239000004480 active ingredient Substances 0.000 description 31
235000013399 edible fruits Nutrition 0.000 description 30
238000011282 treatment Methods 0.000 description 26
239000000463 material Substances 0.000 description 24
239000004094 surface-active agent Substances 0.000 description 24
241000238876 Acari Species 0.000 description 23
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239000007788 liquid Substances 0.000 description 20
241000221785 Erysiphales Species 0.000 description 19
239000000843 powder Substances 0.000 description 18
239000002689 soil Substances 0.000 description 17
244000070406 Malus silvestris Species 0.000 description 15
230000006378 damage Effects 0.000 description 15
239000003085 diluting agent Substances 0.000 description 15
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
239000007858 starting material Substances 0.000 description 15
239000002245 particle Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000007921 spray Substances 0.000 description 14
206010039509 Scab Diseases 0.000 description 13
201000010099 disease Diseases 0.000 description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
239000000428 dust Substances 0.000 description 13
230000000694 effects Effects 0.000 description 13
150000003839 salts Chemical class 0.000 description 13
235000011430 Malus pumila Nutrition 0.000 description 12
235000015103 Malus silvestris Nutrition 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000000725 suspension Substances 0.000 description 12
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238000002329 infrared spectrum Methods 0.000 description 11
239000000126 substance Substances 0.000 description 11
239000003995 emulsifying agent Substances 0.000 description 10
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
240000007594 Oryza sativa Species 0.000 description 9
235000007164 Oryza sativa Nutrition 0.000 description 9
239000000654 additive Substances 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
235000009566 rice Nutrition 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000443 aerosol Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
235000013601 eggs Nutrition 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 7
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241001454295 Tetranychidae Species 0.000 description 7
238000010521 absorption reaction Methods 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
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230000002538 fungal effect Effects 0.000 description 7
238000003306 harvesting Methods 0.000 description 7
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241000894007 species Species 0.000 description 7
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 7
239000004563 wettable powder Substances 0.000 description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 6
DJYWNBIJMHTYFH-UHFFFAOYSA-N [1-(hexylcarbamoyl)benzimidazol-2-yl]carbamic acid Chemical compound C(CCCCC)NC(=O)N1C(=NC2=C1C=CC=C2)NC(=O)O DJYWNBIJMHTYFH-UHFFFAOYSA-N 0.000 description 6
229910052784 alkaline earth metal Inorganic materials 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
230000015556 catabolic process Effects 0.000 description 6
239000000417 fungicide Substances 0.000 description 6
150000002334 glycols Chemical class 0.000 description 6
230000012010 growth Effects 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
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CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 5
229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
239000002202 Polyethylene glycol Substances 0.000 description 5
235000006040 Prunus persica var persica Nutrition 0.000 description 5
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
235000021307 Triticum Nutrition 0.000 description 5
241000209140 Triticum Species 0.000 description 5
239000011149 active material Substances 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
235000020971 citrus fruits Nutrition 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
229940117927 ethylene oxide Drugs 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
235000013312 flour Nutrition 0.000 description 5
235000013305 food Nutrition 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
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239000010455 vermiculite Substances 0.000 description 5
229910052902 vermiculite Inorganic materials 0.000 description 5
235000019354 vermiculite Nutrition 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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150000001340 alkali metals Chemical class 0.000 description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
239000011575 calcium Substances 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
150000001720 carbohydrates Chemical class 0.000 description 4
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235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 4
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NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
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238000002156 mixing Methods 0.000 description 4
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239000003973 paint Substances 0.000 description 4
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235000019333 sodium laurylsulphate Nutrition 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
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IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 3
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