CH499265A

CH499265A - Milbenovicid und Fungicid bzw. gegen Milben und Fungi geschütztes nichttextiles Material

Milbenovicid und Fungicid bzw. gegen Milben und Fungi geschütztes nichttextiles Material

Info

Publication number: CH499265A
Authority: CH; Switzerland
Prior art keywords: carbon atoms; ester; methyl ester; benzimidazole; radical
Prior art date: 1966-05-06

Application number

CH625667A

Other languages

German (de)

English (en)

Inventor

Louis Klopping Hein

Original Assignee

Du Pont

Priority date

1966-05-06

Filing date

1967-05-02

Publication date

1970-11-30

1967-05-02 Application filed by Du Pont filed Critical Du Pont

1970-11-30 Publication of CH499265A publication Critical patent/CH499265A/de

Links

230000000855 fungicidal effect Effects 0.000 title claims abstract description 18
230000003151 ovacidal effect Effects 0.000 title abstract description 3
231100000194 ovacidal Toxicity 0.000 title abstract 2
-1 (cyano)methyl Chemical group 0.000 claims abstract description 540
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
229910052736 halogen Inorganic materials 0.000 claims abstract description 17
150000002367 halogens Chemical class 0.000 claims abstract description 17
229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
125000004390 alkyl sulfonyl group Chemical group 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 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
125000000304 alkynyl group Chemical group 0.000 claims abstract 4
125000004430 oxygen atom Chemical group O* 0.000 claims abstract 3
239000002253 acid Substances 0.000 claims description 168
125000004432 carbon atom Chemical group C* 0.000 claims description 115
150000004702 methyl esters Chemical class 0.000 claims description 105
150000001875 compounds Chemical class 0.000 claims description 90
241000238876 Acari Species 0.000 claims description 62
241000233866 Fungi Species 0.000 claims description 48
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
239000000417 fungicide Substances 0.000 claims description 21
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
239000000463 material Substances 0.000 claims description 14
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 11
239000004753 textile Substances 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
125000004965 chloroalkyl group Chemical group 0.000 claims description 6
125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
239000011737 fluorine Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000006501 nitrophenyl group Chemical group 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
239000004480 active ingredient Substances 0.000 abstract description 75
239000000203 mixture Substances 0.000 abstract description 65
238000006243 chemical reaction Methods 0.000 abstract description 21
239000012948 isocyanate Substances 0.000 abstract description 18
150000002513 isocyanates Chemical class 0.000 abstract description 18
WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical compound C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 abstract description 9
150000001412 amines Chemical class 0.000 abstract description 9
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
125000000623 heterocyclic group Chemical group 0.000 abstract 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 105
241000196324 Embryophyta Species 0.000 description 87
238000011282 treatment Methods 0.000 description 50
239000003795 chemical substances by application Substances 0.000 description 45
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
239000004094 surface-active agent Substances 0.000 description 35
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 32
239000007921 spray Substances 0.000 description 32
150000002148 esters Chemical class 0.000 description 31
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 30
235000013399 edible fruits Nutrition 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
231100000676 disease causative agent Toxicity 0.000 description 23
239000007788 liquid Substances 0.000 description 22
239000002904 solvent Substances 0.000 description 22
238000003756 stirring Methods 0.000 description 22
238000002360 preparation method Methods 0.000 description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 19
239000002689 soil Substances 0.000 description 19
239000004563 wettable powder Substances 0.000 description 19
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 18
239000004615 ingredient Substances 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
239000007787 solid Substances 0.000 description 18
125000004494 ethyl ester group Chemical group 0.000 description 17
239000002245 particle Substances 0.000 description 17
239000000725 suspension Substances 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
230000006378 damage Effects 0.000 description 16
201000010099 disease Diseases 0.000 description 16
239000000126 substance Substances 0.000 description 16
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 14
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 13
239000000428 dust Substances 0.000 description 13
230000000694 effects Effects 0.000 description 13
235000013601 eggs Nutrition 0.000 description 13
238000005507 spraying Methods 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
YAURMDVFWWAYJC-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)propanamide Chemical compound C1=CC=C2NC(NC(=O)CC)=NC2=C1 YAURMDVFWWAYJC-UHFFFAOYSA-N 0.000 description 12
239000000843 powder Substances 0.000 description 12
239000011734 sodium Substances 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
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 11
239000000443 aerosol Substances 0.000 description 11
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000002474 experimental method Methods 0.000 description 10
KBRSJPHSCOAFDR-UHFFFAOYSA-N 3-chloro-6-methyl-5,5-dioxo-11h-benzo[c][2,1]benzothiazepin-11-ol Chemical compound O=S1(=O)N(C)C2=CC=CC=C2C(O)C2=CC=C(Cl)C=C21 KBRSJPHSCOAFDR-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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235000013339 cereals Nutrition 0.000 description 9
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 9
239000003973 paint Substances 0.000 description 9
244000070406 Malus silvestris Species 0.000 description 8
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
238000003306 harvesting Methods 0.000 description 8
238000000034 method Methods 0.000 description 8
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 7
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 7
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 7
235000011430 Malus pumila Nutrition 0.000 description 7
235000015103 Malus silvestris Nutrition 0.000 description 7
239000005642 Oleic acid Substances 0.000 description 7
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
239000000654 additive Substances 0.000 description 7
235000014113 dietary fatty acids Nutrition 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
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239000000194 fatty acid Substances 0.000 description 7
229930195729 fatty acid Natural products 0.000 description 7
238000001914 filtration Methods 0.000 description 7
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 7
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240000005561 Musa balbisiana Species 0.000 description 6
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AXPZGGIIXCYPQK-UHFFFAOYSA-N OS(=O)P(O)(O)=O Chemical compound OS(=O)P(O)(O)=O AXPZGGIIXCYPQK-UHFFFAOYSA-N 0.000 description 6
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150000001263 acyl chlorides Chemical class 0.000 description 6
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239000002270 dispersing agent Substances 0.000 description 6
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HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 6
229910052903 pyrophyllite Inorganic materials 0.000 description 6
235000019333 sodium laurylsulphate Nutrition 0.000 description 6
238000012360 testing method Methods 0.000 description 6
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241000109329 Rosa xanthina Species 0.000 description 5
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230000000996 additive effect Effects 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
238000013459 approach Methods 0.000 description 5
235000021015 bananas Nutrition 0.000 description 5
MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical compound C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 description 5
238000010410 dusting Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
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HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
229940045998 sodium isethionate Drugs 0.000 description 5
LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 5
238000003860 storage Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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238000005406 washing Methods 0.000 description 5
IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 4
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 4
244000291564 Allium cepa Species 0.000 description 4
235000002732 Allium cepa var. cepa Nutrition 0.000 description 4
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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150000001556 benzimidazoles Chemical class 0.000 description 4
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OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 4
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KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 4
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JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 3
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RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 3
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