DE3717815A1 - Fungicidal compositions based on substituted cyanamides - Google Patents
Fungicidal compositions based on substituted cyanamidesInfo
- Publication number
- DE3717815A1 DE3717815A1 DE19873717815 DE3717815A DE3717815A1 DE 3717815 A1 DE3717815 A1 DE 3717815A1 DE 19873717815 DE19873717815 DE 19873717815 DE 3717815 A DE3717815 A DE 3717815A DE 3717815 A1 DE3717815 A1 DE 3717815A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- alkoxy
- halogen
- optionally substituted
- substituted
- 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- Withdrawn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
- 150000001912 cyanamides Chemical class 0.000 title claims abstract description 22
- 239000000203 mixture Substances 0.000 title claims description 19
- 230000000855 fungicidal effect Effects 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims abstract description 13
- 241000233866 Fungi Species 0.000 claims abstract 3
- -1 aralkenyl Chemical group 0.000 claims description 73
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 229910052717 sulfur Chemical group 0.000 claims description 23
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 239000011593 sulfur Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 6
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 6
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 8
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000000417 fungicide Substances 0.000 description 7
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 7
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 241000231139 Pyricularia Species 0.000 description 5
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 4
- 241000220225 Malus Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000228453 Pyrenophora Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 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 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- WICJDHDKSYTQLS-UHFFFAOYSA-N (3-nitrophenyl)cyanamide Chemical compound [O-][N+](=O)C1=CC=CC(NC#N)=C1 WICJDHDKSYTQLS-UHFFFAOYSA-N 0.000 description 2
- LIBMQHFYQQYKQQ-UHFFFAOYSA-N (4-fluorophenyl)cyanamide Chemical compound FC1=CC=C(NC#N)C=C1 LIBMQHFYQQYKQQ-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- GKFFFNUVYUGXEW-UHFFFAOYSA-N 4-chlorophenyl cyanamide Natural products ClC1=CC=C(NC#N)C=C1 GKFFFNUVYUGXEW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000371644 Curvularia ravenelii Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
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- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
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- ITIDSNKGTOBPBD-UHFFFAOYSA-N hydroxy-phenyl-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(=S)C1=CC=CC=C1 ITIDSNKGTOBPBD-UHFFFAOYSA-N 0.000 description 1
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- 235000010445 lecithin Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [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 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- ISPSODPTYQOENZ-UHFFFAOYSA-N methyl 4-(cyanoamino)benzoate Chemical compound COC(=O)C1=CC=C(NC#N)C=C1 ISPSODPTYQOENZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- YNAZROFSPQHGJN-UHFFFAOYSA-N n-(4-chlorophenyl)-n-cyano-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C#N)C1=CC=C(Cl)C=C1 YNAZROFSPQHGJN-UHFFFAOYSA-N 0.000 description 1
- RBPNNMWMDRQWKQ-UHFFFAOYSA-N n-(4-chlorophenyl)-n-cyanobenzamide Chemical compound C1=CC(Cl)=CC=C1N(C#N)C(=O)C1=CC=CC=C1 RBPNNMWMDRQWKQ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- IJOQLKXNRSWATI-UHFFFAOYSA-N n-methylmethanamine;hydrochloride Chemical compound Cl.CNC.CNC IJOQLKXNRSWATI-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003578 thiophosphoric acid amides Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- QGDIJZMKEQCRBX-UHFFFAOYSA-N zinc;ethene Chemical group [Zn+2].[CH-]=C.[CH-]=C QGDIJZMKEQCRBX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
-
- 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
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Die Erfindung betrifft die Verwendung von teilweise bekannten substituierten Cyanamiden als Fungizide, neue substituierte Cyanamide und ein Verfahren zu ihrer Herstellung.The invention relates to the use of partially known substituted cyanamides as fungicides, new substituted cyanamides and a process for their preparation.
Es ist bekannt, daß man bestimmte Pflanzenkrankheiten durch Wirkstoffe aus den Klassen der Dithiocarbamate und der sulfenylierten Arylsulfamide bekämpfen kann. So können z. B. Zinkethylen-1,2-bis-dithiocarbamidat (Zineb) gegen Venturia im Obstbau und N,N-Dimethyl-N′-phenyl-N′- fluordichlormethylthio-sulfamid (Dichlorfluanid) gegen Pyricularia in Reis angewendet werden (vgl. Phytopathology 33 [1943], 1113, bzw. DE-AS 11 93 498). Die Wirkung dieser bekannten Verbindungen ist jedoch, insbesondere bei niedrigen Wirkstoffkonzentrationen, nicht immer zufriedenstellend. It is known to have certain plant diseases through active substances from the classes of dithiocarbamates and can fight the sulfenylated arylsulfamides. So can e.g. B. Zinc ethylene 1,2-bis-dithiocarbamidate (Zineb) against Venturia in fruit growing and N, N-dimethyl-N'-phenyl-N'- fluorodichloromethylthiosulfamide (dichlorofluoride) against Pyricularia can be used in rice (see Phytopathology 33 [1943], 1113, or DE-AS 11 93 498). The effect of these known compounds, however, is in particular at low drug concentrations, not always satisfactory.
Eine Reihe von substituierten Cyanamiden ist bereits in der Literatur beschrieben (vgl. J. Org. Chem. 29 [1964], 153-157; Synthesis 1975, 111-113; Bull. Soc. Chim. France 1975, 395-397; J. Chem. Res. Synop. 1981, 148; US-PS 37 93 372). Über fungizide Eigenschaften solcher Verbindungen ist jedoch bisher nichts bekanntgeworden.A number of substituted cyanamides are already in described in the literature (cf. J. Org. Chem. 29 [1964], 153-157; Synthesis 1975, 111-113; Bull. Soc. Chim. France 1975, 395-397; J. Chem. Res. Synop. 1981, 148; U.S. Patent 37 93 372). About fungicidal properties of such Connections have so far not become known.
Es wurde nun gefunden, daß die teilweise bekannten substituierten Cyanamide der allgemeinen Formel (I)It has now been found that the partially known substituted Cyanamides of the general formula (I)
in welcher
R¹für gegebenenfalls substituiertes Alkyl oder Aryl
steht und
R²für die Gruppierungen -CO-R³, -SO₂-R⁴ oder
steht, worin
R³für einen gegebenenfalls substituierten Rest
aus der Reihe Alkyl, Cycloalkyl, Alkenyl, Alkinyl,
Aralkyl, Aralkenyl, Aryl, Heteroaryl,
Alkoxy, Aralkoxy, Aryloxy, Alkylthio, Aralkylthio,
Arylthio, Alkylamino, Cycloalkylamino,
Dialkylamino, Aralkylamino oder Arylamino
steht,
R⁴für einen gegebenenfalls substituierten Rest
aus der Reihe Alkyl, Aralkyl, Aryl oder
Heteroaryl steht,
R⁵für einen gegebenenfalls substituierten Rest
aus der Reihe Alkyl, Aryl, Alkoxy, Alkylthio,
Alkylamino oder Dialkylamino steht,
R⁶für einen gegebenenfalls substituierten Rest
aus der Reihe Alkyl, Alkoxy, Alkylthio, Alkylamino
oder Dialkylamino steht und
Qfür Sauerstoff oder Schwefel steht,in which
R¹ stands for optionally substituted alkyl or aryl and R² stands for the groupings -CO-R³, -SO₂-R⁴ or where R³ is an optionally substituted radical from the series alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aralkenyl, aryl, heteroaryl, alkoxy, aralkoxy, aryloxy, alkylthio, aralkylthio, arylthio, alkylamino, cycloalkylamino, dialkylamino, aralkylamino or arylamino R⁴ represents an optionally substituted radical from the series alkyl, aralkyl, aryl or heteroaryl, R⁵ represents an optionally substituted radical from the series alkyl, aryl, alkoxy, alkylthio, alkylamino or dialkylamino, R⁶ represents an optionally substituted radical from the series alkyl, alkoxy, Alkylthio, alkylamino or dialkylamino and Q represents oxygen or sulfur,
starke fungizide Eigenschaften aufweisen.have strong fungicidal properties.
Überraschenderweise zeigen die substituierten Cyanamide der allgemeinen Formel (I) erheblich stärkere fungizide Wirkung als bekannte Fungizide mit vergleichbarem Wirkprofil, wie z. B. Zineb oder Dichlorfluanid.Surprisingly, the substituted cyanamides show the general formula (I) considerably stronger fungicides Effect as known fungicides with a comparable activity profile, such as B. Zineb or dichlorofluoride.
Alle aliphatischen Reste, wie Alkyl, Alkoxy, Alkenyl u. a., allein oder in Zusammensetzungen, sind geradkettig oder verzweigt, auch wenn es nicht ausdrücklich erwähnt ist.All aliphatic radicals, such as alkyl, alkoxy, alkenyl u. a., alone or in compositions, are straight chain or branched, even if it is not specifically mentioned is.
Halogen allein oder in Zusammensetzungen wie Halogenalkyl bedeutet im Text Fluor, Chlor, Brom und Jod, vorzugsweise Fluor, Chlor und Brom, ganz besonders bevorzugt Fluor und Chlor. Halogen alone or in compositions such as haloalkyl in the text means fluorine, chlorine, bromine and iodine, preferably Fluorine, chlorine and bromine, very particularly preferred Fluorine and chlorine.
Die Erfindung betrifft vorzugsweise die Verwendung fungizider Mittel und fungizide Mittel auf Basis von Verbindungen der allgemeinen Formel (I), in welcherThe invention preferably relates to the use of fungicides Compounds and fungicidal compositions based on compounds of the general formula (I), in which
R¹für C₁-C₄-Alkyl steht oder für Phenyl oder Naphthyl steht, welche gegebenenfalls ein- bis mehrfach, gleich oder verschieden substituiert sind durch Halogen, Cyano, Nitro, C₁-C₆-Alkyl, C₁-C₂-Halogenalkyl, C₁-C₄-Alkoxy, C₁-C₂-Halogenalkoxy, C₁-C₄- Alkylthio, C₁-C₂-Halogenalkylthio, C₁-C₄-Alkylsulfinyl, C₁-C₄-Alkylsulfonyl, C₁-C₂-Halogenalkylsulfonyl, C₁-C₄-Alkylamino, Di-(C₁-C₃-alkyl)-amino, C₁-C₄-Alkyl-carbonyl-amino und C₁-C₄-Alkoxy-carbonyl, R²für die Gruppierungen -CO-R³, -SO₂-R⁴ oder steht, worin R³für C₁-C₁₀-Alkyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen und C₁-C₄-Alkoxy substituiert ist, C₃- C₆-Cycloalkyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen und C₁-C₂-Alkyl substituiert ist, C₂-C₁₀- Alkenyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, C₂-C₁₀-Alkinyl, Benzyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden im Ring durch Halogen substituiert ist, Phenylethenyl, Phenyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, C₁-C₄-Alkyl, C₁-C₂-Halogenalkyl, C₁-C₄- Alkoxy und C₁-C₂-Halogenalkoxy substituiert ist, Naphthyl, Furyl, Thienyl, Pyridyl, C₁-C₅- Alkoxy, Benzyloxy, Phenoxy, C₁-C₅-Alkylthio, Benzylthio, Phenylthio, C₁-C₅-Alkylamino, C₃-C₆-Cycloalkylamino, Di-(C₁-C₃- alkyl)-amino, Benzylamino oder Phenylamino, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, C₁-C₄-Alkyl, C₁-C₂-Halogenalkyl, C₁-C₄- Alkoxy, C₁-C₂-Halogenalkoxy, C₁-C₄-Alkylthio, C₁-C₂-Halogenalkylthio, C₁-C₄-Alkylsulfinyl, C₁-C₄-Alkylsulfonyl, C₁-C₂-Halogenalkylsulfonyl und C₁-C₄-Alkoxy-carbonyl substituiert ist, steht, R⁴für C₁-C₁₀-Alkyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, Benzyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, C₁-C₄-Alkyl, C₁-C₂-Halogenalkyl, C₁-C₄- Alkoxy, C₁-C₂-Halogenalkoxy und C₁-C₄-Alkoxy- carbonyl substituiert ist, Phenyl, welches gegebenenfalls durch Halogen, Cyano, Nitro Phenyl, C₁-C₄-Alkyl, C₁-C₂-Halogenalkyl, C₁- C₄-Alkoxy, C₁-C₂-Halogenalkoxy, C₁-C₄-Alkylthio, C₁-C₂-Halogenalkylthio, C₁-C₄-Alkylsulfinyl, C₁-C₄-Halogenalkylsulfonyl, Di-(C₁-C₂- alkyl)-aminosulfonyl und C₁-C₄-Alkoxy-carbonyl substituiert ist, Naphthyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, C₁-C₄-Alkyl, und C₁-C₄-Alkoxy substituiert ist, Thienyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen, C₁-C₄- Alkyl und C₁-C₄-Alkoxy-carbonyl substituiert ist, Pyrazolyl, welches gegebenenfalls durch Halogen, C₁-C₄-Alkyl und C₁-C₄-Alkoxy-carbonyl substituiert ist oder Pyridyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen, C₁-C₄-Alkyl und C₁- C₄-Alkoxy-carbonyl substituiert ist, steht, R⁵für C₁-C₄-Alkyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, Phenyl, C₁-C₄- Alkoxy, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden, durch Halogen substituiert ist, C₁-C₄-Alkylthio, C₁-C₄-Alkylamino oder Di-(C₁-C₃-alkyl)-amino steht, R⁶für C₁-C₄-Alkyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, C₁-C₆-Alkoxy, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, C₁-C₄-Alkylthio, C₁-C₄-Alkylamino oder Di-(C₁-C₃-alkyl)-amino steht, und Qfür Sauerstoff oder Schwefel steht. R¹ is C₁-C₄-alkyl or phenyl or naphthyl, which are optionally substituted one or more times, identically or differently, by halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy , C₁-C₂-haloalkoxy, C₁-C₄-alkylthio, C₁-C₂-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl, C₁-C₄-alkylamino, di- (C₁-C₃- alkyl) amino, C₁-C₄-alkyl-carbonyl-amino and C₁-C₄-alkoxy-carbonyl, R² for the groups -CO-R³, -SO₂-R⁴ or is in which R³ is C₁-C₁ Alkyl-alkyl, which is optionally substituted one or more times, identically or differently by halogen and C₁-C₄-alkoxy, C₃- C₆-cycloalkyl, which is optionally one to more times, identical or different by halogen and C₁-C₂-alkyl is substituted, C₂-C₁₀ alkenyl, which is optionally substituted one or more times, identically or differently by halogen, C₂-C₁₀-alkynyl, benzyl, which is optionally one or more times, identical or different in the ring by Halogen is substituted, phenylethenyl, phenyl, which is optionally substituted one or more times, identically or differently, by halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy and C₁-C₂-haloalkoxy , Naphthyl, furyl, thienyl, pyridyl, C₁-C₅- alkoxy, benzyloxy, phenoxy, C₁-C Alkyl-alkylthio, benzylthio, phenylthio, C₁-C₅-alkylamino, C₃-C₆-cycloalkylamino, di- (C₁-C₃- alkyl) -amino, benzylamino or phenylamino, which may be one or more times, identical or different ieden by halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₄-alkylthio, C₁-C₂-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl and C₁-C₄-alkoxy-carbonyl is substituted, R⁴ is C₁-C₁₀-alkyl which is optionally substituted one or more times, identically or differently by halogen, benzyl, which is optionally mono- to polysubstituted, identically or differently, by halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₁-C₄-alkoxycarbonyl, phenyl which is optionally substituted by halogen, cyano, nitro phenyl, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₄-alkylthio, C₁-C₂-haloalkylthio, C₁-C₄ -Alkylsulfinyl, C₁-C₄-haloalkylsulfonyl, di- (C₁-C₂-alkyl) -aminosulfonyl and C₁-C₄-alkoxy-carbonyl is substituted, naphthyl, which is optionally one to more, identical or different, by halogen, cyano, N itro, C₁-C₄-alkyl, and C₁-C₄-alkoxy is substituted, thienyl, which is optionally substituted one or more times, identically or differently, by halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy-carbonyl, pyrazolyl, which is optionally substituted by halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy-carbonyl or pyridyl, which is optionally substituted one or more times, identically or differently, by halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy-carbonyl is, R⁵ is C₁-C₄-alkyl, which is optionally substituted one or more times, identically or differently by halogen, phenyl, C₁-C₄-alkoxy, which is optionally substituted one or more times, identically or differently, by halogen, C₁-C₄-alkylthio, C₁-C₄-alkylamino or di- (C₁-C₃-alkyl) -amino, R⁶ for C₁-C₄-alkyl, which is optionally substituted one or more times, identically or differently by halogen, C₁-C₆ Alkoxy which is optionally substituted one or more times, identically or differently, by halogen, C₁-C₄-alkylthio, C₁-C₄-alkylamino or di- (C₁-C₃-alkyl) -amino, and Q represents oxygen or sulfur.
Besonders bevorzugt werden erfindungsgemäß die Verbindungen der Formel (I) verwendet, in welcherAccording to the invention, the compounds are particularly preferred of formula (I) used, in which
R¹für Phenyl steht, welches gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiert ist durch Fluor, Chlor, Brom, Methyl, Ethyl, Cyano, Nitro, Trifluormethyl, Trichlormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylamino, Ethylamino, Dimethylamino, Diethylamino, Trifluormethylthio, Acetylamino, Propionylamino, Methoxycarbonyl, Ethoxycarbonyl, Propoxycarbonyl und Isopropoxycarbonyl, R²für die Gruppierungen -CO-R³, -SO₂-R⁴ oder steht, worin R³für Phenyl steht, welches gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiert ist durch Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, Trifluormethyl, Trichlormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy und Chlordifluormethoxy R⁴für Phenyl steht, welches gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiert ist durch Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Phenyl, Chlormethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, Trifluormethylthio, Dimethylaminosulfonyl, Methoxycarbonyl, Ethoxycarbonyl, Propoxycarbonyl und Isopropoxycarbonyl, R⁵für Methyl, Ethyl, Phenyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylamino, Ethylamino oder Dimethylamino steht, R⁶für Methyl, Ethyl, Methoxy, Ethoxy, Propoxy, Butoxy, Pentyloxy, Hexyloxy, Methylthio, Ethylthio, Propylthio, Butylthio, Methylamino, Ethylamino oder Dimethylamino steht und Qfür Sauerstoff oder Schwefel steht.R¹ is phenyl, which is optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, cyano, nitro, trifluoromethyl, trichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylamino, ethylamino , Dimethylamino, diethylamino, trifluoromethylthio, acetylamino, propionylamino, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl, R² for the groups -CO-R³, -SO₂-R⁴ or is where R³ is phenyl which is optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and chlorodifluoromethoxy R⁴ is phenyl which is optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, phenyl, chloromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, trifluoromethylthio, dimethylaminosulfonyl, methoxycarbonyl, Ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl, R⁵ is methyl, ethyl, phenyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, R⁶ is methyl, ethyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, methylthio, ethylthio, propylthio , Butylthio, methylamino, ethylamino or dimethylamino and Q represents oxygen or sulfur.
Als Beispiele für die erfindungsgemäß zu verwendenden
Verbindungen der Formel (I) seien genannt:
N-(3,4-Dichlor-phenyl)-N-(ethoxy-ethylthionophosphoryl)-
cyanamid, N-Benzoyl-N-(3-nitro-phenyl)-cyanamid, N-Benzoyl-
N-(4-chlor-phenyl)-cyanamid, N-(4-Methoxy-phenyl)-
N-(4-methyl-3-nitro-phenylsulfonyl)-cyanamid, N-(4-Methoxy-
phenyl)-N-(4-chlor-3-nitro-phenylsulfonyl)-cyanamid,
N-(4-Chlor-Phenyl)-N-(2-chlor-5-nitro-phenylsulfonyl)-
cyanamid, N-(4-Chlorphenyl)-N-(2-chlormethyl-phenylsulfonyl)-
cyanamid, N-(4-Chlor-phenyl)-N-(2-chlor-phenylsulfonyl)-
cyanamid, N-(4-Chlorphenyl)-N-(4-methyl-phenylsulfonyl)-
cyanamid, N-(4-Chlor-phenyl)-N-(4-methyl-3-
nitro-phenylsulfonyl)-cyanamid und N-(4-Chlorphenyl)-N-
(2-ethoxycarbonyl-phenylsulfonyl)-cyanamid.
The following may be mentioned as examples of the compounds of the formula (I) to be used according to the invention:
N- (3,4-dichlorophenyl) -N- (ethoxyethylthionophosphoryl) cyanamide, N-benzoyl-N- (3-nitro-phenyl) -cyanamide, N-benzoyl-N- (4-chlorophenyl ) -cyanamide, N- (4-methoxy-phenyl) - N- (4-methyl-3-nitro-phenylsulfonyl) -cyanamide, N- (4-methoxy-phenyl) -N- (4-chloro-3-nitro -phenylsulfonyl) -cyanamide, N- (4-chlorophenyl) -N- (2-chloro-5-nitro-phenylsulfonyl) - cyanamide, N- (4-chlorophenyl) -N- (2-chloromethyl-phenylsulfonyl) - cyanamide, N- (4-chlorophenyl) -N- (2-chlorophenylsulfonyl) - cyanamide, N- (4-chlorophenyl) -N- (4-methylphenylsulfonyl) - cyanamide, N- (4-chlorine -phenyl) -N- (4-methyl-3-nitro-phenylsulfonyl) -cyanamide and N- (4-chlorophenyl) -N- (2-ethoxycarbonyl-phenylsulfonyl) -cyanamide.
Diese Verbindungen werden wegen ihrer hervorragenden fungiziden Wirkung ganz besonders bevorzugt.These connections are excellent because of their fungicidal activity is particularly preferred.
Weitere Beispiele für die erfindungsgemäß zu verwendenden Verbindungen der Formel (I) sind in der nachstehenden Tabelle 1 aufgeführt.Further examples of those to be used according to the invention Compounds of formula (I) are as follows Table 1 listed.
Gegenstand der vorliegenden Erfindung sind weiter neue substituierte Cyanamide der allgemeinen Formel (Ia)The present invention also relates to new ones substituted cyanamides of the general formula (Ia)
in welcherin which
A¹für gegebenenfalls substituiertes Aryl steht, A²für die Gruppierung steht, worin A³für einen gegebenenfalls substituierten Rest aus der Reihe Alkyl, Aryl, Alkoxy, Alkylthio, Alkylamino oder Dialkylamino steht, A⁴für einen gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkoxy, Alkylthio, Alkylamino oder Dialkylamino steht und Qfür Sauerstoff oder Schwefel steht.A¹ is optionally substituted aryl, A² is the grouping where A³ represents an optionally substituted radical from the series alkyl, aryl, alkoxy, alkylthio, alkylamino or dialkylamino, A⁴ represents an optionally substituted radical from the series alkyl, alkoxy, alkylthio, alkylamino or dialkylamino and Q represents oxygen or sulfur.
Man erhält die neuen Verbindungen der Formel (Ia), wenn man Cyanamide der Formel (IIa)The new compounds of the formula (Ia) are obtained if cyanamides of the formula (IIa)
N≡C-NH-A¹ (IIa)N≡C-NH-A¹ (IIa)
in welcherin which
A¹die oben angegebene Bedeutung hat, A¹ has the meaning given above,
mit Verbindungen der Formel (IIIa)with compounds of the formula (IIIa)
Cl-A² (IIIa)Cl-A² (IIIa)
in welcherin which
A²die oben angegebene Bedeutung hat,A² has the meaning given above,
gegebenenfalls in Gegenwart eines Säureakzeptors und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.optionally in the presence of an acid acceptor and optionally in the presence of a diluent.
Auf prinzipiell gleiche Weise erhält man auch die neuen und bekannten Verbindungen der allgemeinen Formel (I), wenn man Cyanamide der Formel (II)In principle, the new ones are obtained in the same way and known compounds of the general formula (I), if cyanamides of the formula (II)
N≡C-NH-R¹ (II)N≡C-NH-R¹ (II)
in welcherin which
R¹die oben angegebene Bedeutung hat,R¹ has the meaning given above,
mit Verbindungen der Formel (III)with compounds of formula (III)
Cl-R² (III)Cl-R² (III)
in welcherin which
R²die oben angegebene Bedeutung hat,R² has the meaning given above,
gegebenenfalls in Gegenwart eines Säureakzeptors und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.optionally in the presence of an acid acceptor and optionally in the presence of a diluent.
Bevorzugt werden die neuen substituierten Cyanamide der Formel (Ia), in welcherThe new substituted cyanamides are preferred Formula (Ia) in which
A¹für Phenyl oder Naphthyl steht, welche gegebenenfalls ein- bis mehrfach, gleich oder verschieden substituiert sind durch Halogen, Cyano, Nitro, C₁- C₄-Alkyl, C₁-C₂-Halogenalkyl, C₁-C₄-Alkoxy, C₁-C₂- Halogenalkoxy, C₁-C₄-Alkylthio, C₁-C₂-Halogenalkylthio, C₁-C₄-Alkylsulfinyl, C₁-C₄-Alkylsulfonyl, C₁- C₂-Halogenalkylsulfonyl, C₁-C₄-Alkylamino, Di-(C₁- C₃-alkyl)-amino, C₁-C₄-Alkyl-carbonyl-amino und C₁- C₄-Alkoxy-carbonyl, A²für die Gruppierung steht, worin A³für C₁-C₄-Alkyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, Phenyl, C₁-C₄-Alkoxy, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, C₁-C₄-Alkylthio, C₁-C₄- Alkylamino oder Di-(C₁-C₃-alkyl)-amino steht, A⁴für C₁-C₄-Alkyl, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, C₁-C₄-Alkoxy, welches gegebenenfalls ein- bis mehrfach, gleich oder verschieden durch Halogen substituiert ist, C₁-C₄-Alkylthio, C₁-C₄-Alkylamino oder Di-(C₁-C₃-alkyl)-amino steht und Qfür Sauerstoff oder Schwefel steht.A¹ is phenyl or naphthyl, which are optionally substituted one or more times, identically or differently, by halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂- haloalkoxy, C₁ -C₄-alkylthio, C₁-C₂-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl, C₁-C₄-alkylamino, di- (C₁-C₃-alkyl) -amino, C₁-C₄ -Alkyl-carbonyl-amino and C₁- C₄-alkoxy-carbonyl, A² for the grouping where A³ is C₁-C₄-alkyl, which is optionally substituted one or more times, identically or differently by halogen, phenyl, C₁-C₄-alkoxy, which is optionally substituted one or more times, identically or differently by halogen, C₁- C₄-alkylthio, C₁-C₄- alkylamino or di- (C₁-C₃-alkyl) -amino, A⁴ for C₁-C₄-alkyl, which is optionally substituted one or more times, identically or differently by halogen, C₁-C₄-alkoxy , which is optionally substituted one or more times, identically or differently by halogen, C₁-C Alkyl-alkylthio, C₁-C₄-alkylamino or di- (C₁-C₃-alkyl) -amino and Q represents oxygen or sulfur.
Besonders bevorzugt werden die neuen Verbindungen der Formel (Ia), in welcherThe new compounds are particularly preferred Formula (Ia) in which
A¹für Phenyl steht, welches gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiert ist durch Fluor, Chlor, Brom, Methyl, Ethyl, Cyano, Nitro, Trifluormethyl, Trichlormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylamino, Ethylamino, Dimethylamino, Diethylamino, Trifluormethylthio, Acetylamino, Propionylamino, Methoxycarbonyl, Ethoxycarbonyl, Propoxycarbonyl und Isopropoxycarbonyl, A²für die Gruppierung steht, worin A³für Methyl, Ethyl, Phenyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Methylamino, Ethylamino oder Dimethylamino steht, A⁴für Methyl, Ethyl, Methoxy, Ethoxy, Propoxy, Butoxy, Pentyloxy, Hexyloxy, Methylthio, Ethylthio, Propylthio, Butylthio, Methylamino, Ethylamino oder Dimethylamino steht und Qfür Sauerstoff oder Schwefel steht.A¹ represents phenyl, which is optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, cyano, nitro, trifluoromethyl, trichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylamino, ethylamino , Dimethylamino, diethylamino, trifluoromethylthio, acetylamino, propionylamino, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl, A² for the grouping where A³ is methyl, ethyl, phenyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, A⁴ is methyl, ethyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, methylthio, ethylthio, propylthio, butylthio, Methylamino, ethylamino or dimethylamino and Q represents oxygen or sulfur.
Verwendet man als Ausgangsstoffe beim Verfahren zur Herstellung der neuen Verbindungen der Formel (Ia) beispielsweise N-(4-Fluor-phenyl)-cyanamid und Phosphorsäure- chlorid-dimethylester, so kann der Reaktionsablauf durch folgendes Formelschema skizziert werden:Used as starting materials in the manufacturing process the new compounds of formula (Ia) for example N- (4-fluorophenyl) cyanamide and phosphoric acid chloride dimethyl ester, so the reaction can can be outlined by the following formula:
Die als Ausgangsstoffe zu verwendenden Cyanamide sind durch die Formel (IIa) allgemein definiert. In Formel (IIa) hat A¹ vorzugsweise bzw. insbesondere die gleiche Bedeutung, wie sie oben bei der Beschreibung der neuen Wirkstoffe der Formel (Ia) für A¹ als bevorzugt bzw. als besonders bevorzugt angegeben ist.The cyanamides to be used as starting materials are generally defined by the formula (IIa). In formula (IIa) A¹ preferably or in particular has the same Meaning as described above when describing the new Active substances of the formula (Ia) for A¹ as preferred or as is particularly preferred.
Als Beispiele für die Ausgangsstoffe der Formel (IIa)
seien genannt:
N-Phenyl-cyanamid, N-(4-Fluor-phenyl)-cyanamid, N-(4-
Chlor-phenyl)-cyanamid, N-(3-Chlor-phenyl)-cyanamid, N-
(2-Chlor-phenyl)-cyanamid, N-(3,4-Dichlor-phenyl)-cyanamid,
N-(4-Nitro-phenyl)-cyanamid, N-(3-Nitro-phenyl)-
cyanamid, N-(4-Methoxy-phenyl)-cyanamid, N-(3-Methoxy-
phenyl)-cyanamid, N-(4-Trifluormethyl-phenyl)-cyanamid,
N-(3-Trifluormethyl-phenyl)-cyanamid, N-(4-Methyl-phenyl)-
cyanamid, N-(3-Methyl-phenyl)-cyanamid, N-(2-Chlor-
5-trifluormethyl-phenyl)-cyanamid, N-(3-Acetylamino-4-
methyl-phenyl)-cyanamid, N-(2-Methoxy-5-nitro-phenyl)-
cyanamid, N-(4-trifluormethoxy-phenyl)-cyanamid, N-(2-
Methyl-5-nitro-phenyl)-cyanamid, N-(4-Methoxycarbonyl-
phenyl)-cyanamid, N-(4-Cyano-phenyl)-cyanamid, N-(4-Methylthio-
phenyl)-cyanamid und N-(4-trifluormethylthio-
phenyl)-cyanamid.Examples of the starting materials of the formula (IIa) are:
N-phenyl-cyanamide, N- (4-fluorophenyl) cyanamide, N- (4-chlorophenyl) cyanamide, N- (3-chlorophenyl) cyanamide, N- (2-chlorophenyl ) -cyanamide, N- (3,4-dichlorophenyl) -cyanamide, N- (4-nitro-phenyl) -cyanamide, N- (3-nitro-phenyl) -cyanamide, N- (4-methoxy-phenyl ) -cyanamide, N- (3-methoxyphenyl) -cyanamide, N- (4-trifluoromethyl-phenyl) -cyanamide, N- (3-trifluoromethyl-phenyl) -cyanamide, N- (4-methylphenyl) - cyanamide, N- (3-methylphenyl) cyanamide, N- (2-chloro-5-trifluoromethylphenyl) cyanamide, N- (3-acetylamino-4-methylphenyl) cyanamide, N- (2nd -Methoxy-5-nitro-phenyl) - cyanamide, N- (4-trifluoromethoxy-phenyl) -cyanamide, N- (2-methyl-5-nitro-phenyl) -cyanamide, N- (4-methoxycarbonylphenyl) - cyanamide, N- (4-cyanophenyl) cyanamide, N- (4-methylthiophenyl) cyanamide and N- (4-trifluoromethylthiophenyl) cyanamide.
Die Ausgangsstoffe der Formel (IIa) sind bekannt (vgl. Houben-Weyl, Methoden der organischen Chemie, Band 8, S. 172-177, und Band E4, S. 981-985; Org. Syn., Coll. Vol. 4, 172-174; DE-OS 35 38 128).The starting materials of the formula (IIa) are known (cf. Houben-Weyl, Methods of Organic Chemistry, Volume 8, Pp. 172-177, and volume E4, pp. 981-985; Org. Syn., Coll. Vol. 4, 172-174; DE-OS 35 38 128).
Die weiter als Ausgangsstoffe zu verwendenden Verbindungen sind durch die Formel (IIIa) allgemein definiert.The compounds to be used as starting materials are generally defined by the formula (IIIa).
In Formel (IIIa) hat A² vorzugsweise bzw. insbesondere die gleiche Bedeutung, wie sie oben bei der Beschreibung der neuen Wirkstoffe der Formel (Ia) für A² als bevorzugt bzw. als besonders bevorzugt angegeben ist.In formula (IIIa), A² preferably or in particular the same meaning as described above in the description of the new active compounds of the formula (Ia) as preferred for A² or is indicated as being particularly preferred.
Als Beispiele für die Ausgangsstoffe der Formel (IIIa)
seien genannt:
Dimethylphosphinsäurechlorid, Dimethylthiophosphinsäure-
chlorid, Methan-, Ethan- und Benzol-phosphonsäure-chlorid-
methylester, -ethylester, -propylester, -butylester,
-pentylester und -hexylester, Methan-, Ethan- und Benzol-
thiophosphonsäure-chlorid-S-methylester, -S-ethylester,
-S-propylester, -S-butylester, -S-pentylester und
-S-hexylester, Methanphosphonsäure-amid-chlorid, Methanphosphonsäure-
chlorid-methylamid, -ethylamid, -propylamid
und -butylamind, Methan-, Ethan- und Benzol-thiophosphonsäure-
chlorid-O-methylester, -O-ethylester, -O-propylester,
-O-butylester, -O-pentylester und -O-hexylester,
Methan, Ethan- und Benzol-dithiophosphonsäure-chlorid-
methylester, -ethylester, -propylester, -butylester,
-pentylester und -hexylester, Methan-, Ethan- und Benzol-
thiophosphonsäureamid-chlorid, Methan-, Ethan- und
Benzol-thiophosphonsäure-chlorid-methylamid, -ethylamid,
-propylamid und -butylamid, Phosphorsäure-chlorid-dimethylester,
-diethylester, -dipropylester, -dibutylester,
-methylester-ethylester, -methylester-propylester, -methylester-
butylester, -ethylester-propylester, -ethylester-
butylester und -propylester-butylester, -ethylester-
butylester und -propylester-butylester, Thiophosphorsäure-
chlorid-O,S-dimethylester, -O,S-diethylester,
-O,S-dipropylester, -O,S-dibutylester, -O-methylester-S-
ethylester, -O-methylester-S-propylester, -O-methylester-
S-butylester, -O-ethylester-S-methylester, -O-
ethylester-S-propylester, -O-ethylester-S-butylester,
-O-propylester-S-methylester, -O-propylester-S-ethylester,
-O-propylester-S-butylester, -O-butylester-S-methylester,
-O-butylester-S-ethylester und -O-butylester-
S-propylester, Phosphorsäure-amid-chlorid-methylester,
-ethylester, -propylester und -butylester, Phosphorsäure-
chlorid-methylamid-methylester, -methylamid-ethylester,
-methylamid-propylester, -methylamid-butylester,
-ethylamid-methylester, -ethylamid-ethylester, -ethylamid-
propylester, -ethylamid-butylester, -propylamid-methylester,
-propylamid-ethylester, -propylamid-propylester,
-propylamid-butylester, -butylamid-methylester,
-butylamid-ethylester, -butylamid-propylester und -butylamid-
butylester, Dithiophosphorsäure-chlorid-S,S-dimethylester-,
-S,S-diethylester, -S,S-dipropylester und
-S,S-dibutylester, Thiophosphorsäure-chlorid-methylamid-
S-methylester, -methylamid-S-ethylester, -methylamid-S-
propylester, -ethylamid-S-propylester, -propylamid-S-methylester,
-propylamid-S-ethylester und -propylamid-S-
propylester, Phosphorsäure-chlorid-bis-dimethylamid und
-bis-diethylamid, Thiophosphorsäure-chlorid-O,O-dimethylester,
-O,O-diethylester, -O,O-dipropylester, -O,O-
dibutylester, -O-methylester--O-ethylester, -O-methylester-
O-propylester, -O-methylester-O-butylester, -O-
ethylester-O-propylester, -O-ethylester-O-butylester und
-O-propylester-O-butylester, Dithiophosphorsäure-chlorid-
O,S-dimethylester, -O,S-diethylester, -O,S-dipropylester,
-O,S-dibutylester, -O-methylester-S-ethylester,
-O-methylester-S-propylester, -O-methylester-S-butylester,
-O-ethylester-S-propylester, -O-ethylester-S-butylester,
-O-ethylester-S-methylester, -O-propylester-S-
methylester, -O-propylester-S-ethylester, -O-propylester-
S-butylester, -O-butylester-S-methylester, -O-butylester-
S-ethylester und -O-butylester-S-propylester,
Thiophosphorsäure-amid-chlorid-O-methylester, -O-ethylester,
-O-propylester und -O-butylester, Thiophosphorsäure-
chlorid-methylamid-O-methylester, -methylamid-O-
ethylester, -methylamid-O-propylester, -methylamid-O-
butylester, -ethylamid-O-methylester, -ethylamid-O-
ethylester, -ethylamid-O-propylester, -ethylamid-O-butylester,
-propylamid-O-methylester, -propylamid-O-
ethylester, -propylamid-O-propylester, propylamid-O-butylester,
-butylamid-O-methylester, -butylamid-O-ethylester,
-butylamid-O-propylester und butylamid-O-butylester,
Trithiophosphorsäure-chlorid-S,S-dimethylester,
-S,S-diethylester, -S,S-dipropylester und -S,S-dibutylester,
Thiophosphorsäure-chlorid-bis-dimethylamid und
-bis-diethylamid.Examples of the starting materials of the formula (IIIa) are:
Dimethylphosphinic acid chloride, dimethylthiophosphinic acid chloride, methane, ethane and benzene-phosphonic acid chloride, methyl ester, ethyl ester, propyl ester, butyl ester, pentyl ester and hexyl ester, methane, ethane and benzene thiophosphonic acid chloride S-methyl ester , -S-ethyl ester, -S-propyl ester, -S-butyl ester, -S-pentyl ester and -S-hexyl ester, methanephosphonic acid amide chloride, methanephosphonic acid chloride methylamide, ethylamide, propylamide and butylamine, methane, Chloride-O-methyl ester, -O-ethyl ester, -O-propyl ester, -O-butyl ester, -O-pentyl ester and -O-hexyl ester, methane, ethane and benzene-dithiophosphonic acid chloride-methyl ester , ethyl ester, propyl ester, butyl ester, pentyl ester and hexyl ester, methane, ethane and benzene thiophosphonic acid amide chloride, methane, ethane and benzene thiophosphonic acid chloride methyl amide, ethyl amide, propyl amide and butyl amide , Phosphoric acid chloride dimethyl ester, diethyl ester, dipropyl ester, dibutyl ester, -m ethyl ester-ethyl ester, -methyl ester-propyl ester, -methyl ester-butyl ester, -ethyl ester-propyl ester, -ethyl ester-butyl ester and -propyl ester-butyl ester, -ethyl ester-butyl ester and -propyl ester-butyl ester, thiophosphoric acid chloride-O, S-dimethyl ester, - O, S-diethyl ester, -O, S-dipropyl ester, -O, S-dibutyl ester, -O-methyl ester-S-ethyl ester, -O-methyl ester-S-propyl ester, -O-methyl ester-S-butyl ester, -O- ethyl ester-S-methyl ester, -O-ethyl ester-S-propyl ester, -O-ethyl ester-S-butyl ester, -O-propyl ester-S-methyl ester, -O-propyl ester-S-ethyl ester, -O-propyl ester-S-butyl ester , -O-butyl ester-S-methyl ester, -O-butyl ester-S-ethyl ester and -O-butyl ester-S-propyl ester, phosphoric acid amide chloride methyl ester, ethyl ester, propyl ester and butyl ester, phosphoric acid chloride methyl amide methyl ester, methyl amide ethyl ester, methyl amide propyl ester, methyl amide butyl ester, ethyl amide methyl ester, ethyl amide ethyl ester, ethyl amide propyl ester, ethyl amide butyl ester, propyl amide methyl ester, propyl amide ethyl ester, propyl amide propyl ester, propyl amide butyl ester, butyl amide methyl ester, butyl amide ethyl ester, butyl amide propyl ester and butyl amide butyl ester, dithiophosphoric acid chloride S, S dimethyl ester, S, S diethyl ester, -S, S-dipropylester and -S, S-dibutyl ester, thiophosphoric acid chloride-methylamide- S-methyl ester, -methylamide-S-ethyl ester, -methylamide-S-propyl ester, -ethylamide-S-propyl ester, -propylamide-S- methyl ester, propylamide S-ethyl ester and propylamide S-propyl ester, phosphoric acid chloride-bis-dimethylamide and -bis-diethylamide, thiophosphoric acid chloride-O, O-dimethyl ester, -O, O-diethyl ester, -O, O -dipropyl ester, -O, O-dibutyl ester, -O-methyl ester - O-ethyl ester, -O-methyl ester-O-propyl ester, -O-methyl ester-O-butyl ester, -O- ethyl ester-O-propyl ester, -O- ethyl ester-O-butyl ester and -O-propyl ester-O-butyl ester, dithiophosphoric acid chloride-O, S-dimethyl ester, -O, S-diethyl ester, -O, S-dipropyl ester, -O, S-dibutyl ester, -O-methyl ester -S-ethyl ester, -O-methyl ester-S-propyl ester, -O-me thylester-S-butyl ester, -O-ethyl ester-S-propyl ester, -O-ethyl ester-S-butyl ester, -O-ethyl ester-S-methyl ester, -O-propyl ester-S-methyl ester, -O-propyl ester-S-ethyl ester , -O-propyl ester-S-butyl ester, -O-butyl ester-S-methyl ester, -O-butyl ester-S-ethyl ester and -O-butyl ester-S-propyl ester, thiophosphoric acid amide chloride-O-methyl ester, -O- ethyl ester, -O-propyl ester and -O-butyl ester, thiophosphoric acid chloride-methylamide-O-methyl ester, -methylamide-O-ethyl ester, -methylamide-O-propyl ester, -methylamide-O-butyl ester, -ethylamide-O-methyl ester, -ethylamide-O-ethyl ester, -ethylamide-O-propyl ester, -ethylamide-O-butyl ester, -propylamide-O-methyl ester, -propylamide-O-ethyl ester, -propylamide-O-propyl ester, propylamide-O-butyl ester, -butylamide -O-methyl ester, -butylamide-O-ethyl ester, -butylamide-O-propyl ester and butylamide-O-butyl ester, trithiophosphoric acid chloride-S, S-dimethyl ester, -S, S-diethyl ester, -S, S-dipropyl ester and - S, S-dibutyl ester, thiophosphoric acid chloride-bis-dimethylamide and -bis-diethyl amid.
Die Ausgangsstoffe der Formel (IIIa) sind bekannt (vgl. Houben-Weyl, Methoden der organischen Chemie, Band 12/1, S. 415-420 und S. 560-563, Band 12/2, S. 274-292, S. 405-408, S. 607-618, S. 621-622 und S. 755- 757, Band E2, S. 333-684).The starting materials of the formula (IIIa) are known (cf. Houben-Weyl, Methods of Organic Chemistry, Volume 12/1, Pp. 415-420 and pp. 560-563, volume 12/2, pp. 274-292, Pp. 405-408, pp. 607-618, pp. 621-622 and pp. 755- 757, volume E2, pp. 333-684).
Das erfindungsgemäße Verfahren zur Herstellung der neuen Verbindungen der Formel (Ia) wird vorzugsweise unter Verwendung von Verdünnungsmitteln durchgeführt. Als Verdünnungsmittel kommen dabei Wasser und praktisch alle inerten organischen Lösungsmittel in Frage. Hierzu gehören vorzugsweise aliphatische und aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe wie Pentan, Hexan, Heptan, Cyclohexan, Petrolether, Benzin, Ligoroin, Benzol, Toluol, Xylol, Methylenchlorid, Ethylenchlorid, Chloroform, Tetrachlorkohlenstoff, Chlorbenzol und o- Dichlorbenzol, Ether wie Diethyl- und Dibutylether, Glykoldimethylether und Diglykoldimethylether, Tetrahydrofuran und Dioxan, Ketone wie Aceton, Methyl-ethyl-, Methyl- isopropyl- und Methyl-isobutyl-keton, Ester wie Essigsäuremethylester und -ethylester oder Nitrile wie z. B. Acetonitril und Propionitril.The inventive method for producing the new Compounds of formula (Ia) is preferably under Use of diluents. As a diluent come water and practically everyone inert organic solvents in question. These include preferably aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, Hexane, heptane, cyclohexane, petroleum ether, gasoline, ligoroin, Benzene, toluene, xylene, methylene chloride, ethylene chloride, Chloroform, carbon tetrachloride, chlorobenzene and o- Dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as Methyl acetate and ethyl acetate or nitriles such as e.g. B. acetonitrile and propionitrile.
Als Säureakzeptoren können bei dem erfindungsgemäßen Verfahren alle üblicherweise für derartige Umsetzungen verwendbaren Säurebindemittel eingesetzt werden. Vorzugsweise in Frage kommen Alkalimetallhydroxide wie z. B. Natrium- und Kaliumhydroxid, Erdalkalihydroxide wie z. B. Calciumhydroxid, Alkalicarbonate und -alkoholate wie Natrium- und Kaliumcarbonat, Natrium- und Kaliummethylat, -ethylat und -tert-butylat, ferner aliphatische, aromatische oder heterocyclische Amine, beispielsweise Triethylamin, Trimethylamin, Dimethylanilin, Dimethylbenzylamin, Pyridin, 1,5-Diazabicyclo-[4,3,0]- non-5-en (DBN), 1,8-Diazabicyclo-[5,4]-undec-7-en (DBU) und 1,4-Diazabicyclo-[2,2,2]-octan (DABCO).As acid acceptors in the invention Procedures all commonly for such implementations usable acid binders can be used. Preferably Alkali metal hydroxides such as e.g. B. sodium and potassium hydroxide, alkaline earth metal hydroxides such as As calcium hydroxide, alkali carbonates and alcoholates such as sodium and potassium carbonate, sodium and potassium methylate, ethylate and tert-butylate, also aliphatic, aromatic or heterocyclic amines, for example Triethylamine, trimethylamine, dimethylaniline, Dimethylbenzylamine, pyridine, 1,5-diazabicyclo- [4,3,0] - non-5-ene (DBN), 1,8-diazabicyclo- [5,4] -undec-7-ene (DBU) and 1,4-diazabicyclo [2,2,2] octane (DABCO).
Die Reaktionstemperaturen können bei dem erfindungsgemäßen Verfahren in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und +80°C, vorzugsweise bei Temperaturen zwischen 0°C und 40°C.The reaction temperatures can in the inventive Procedures can be varied over a wide range. Generally one works at temperatures between -20 ° C and + 80 ° C, preferably at temperatures between 0 ° C and 40 ° C.
Das erfindungsgemäße Verfahren wird im allgemeinen unter Normaldruck durchgeführt.The process according to the invention is generally described in Normal pressure carried out.
Zur Durchführung des erfindungsgemäßen Verfahrens werden die Ausgangsstoffe der Formeln (IIa) und (IIIa) im allgemeinen in angenähert äquimolaren Mengen eingesetzt. Das Reaktionsgemisch wird jeweils mehrere Stunden bei der erforderlichen Temperatur gerührt. Die Aufarbeitung kann nach üblichen Methoden durchgeführt werden. Beispielsweise wird eingeengt, der Rückstand in einem mit Wasser praktisch nicht mischbaren organischen Lösungsmittel, wie z. B. Methylenchlorid, aufgenommen, mit Wasser gewaschen, getrocknet und filtriert. Der nach Abdestillieren des Lösungsmittels vom Filtrat - gegebenenfalls bei leicht erhöhter Temperatur und unter vermindertem Druck - erhaltene Rückstand enthält im wesentlichen das jeweilige Produkt der Formel (Ia).To carry out the method according to the invention the starting materials of the formulas (IIa) and (IIIa) in general used in approximately equimolar amounts. The reaction mixture is in each case for several hours the required temperature is stirred. The workup can be carried out according to usual methods. For example is concentrated, the residue in one with Water practically immiscible organic solvents, such as B. methylene chloride, added with water washed, dried and filtered. The one after distilling off the solvent from the filtrate - if necessary at a slightly elevated temperature and under reduced Pressure - residue obtained essentially contains the respective product of formula (Ia).
Die erfindungsgemäßen Wirkstoffe weisen eine stark mikrobizide Wirkung auf und können zur Bekämpfung von unerwünschten Mikroorganismen praktisch eingesetzt werden. Die Wirkstoffe sind für den Gebrauch als Pflanzenschutzmittel geeignet, besonders als Fungizide.The active compounds according to the invention are highly microbicidal Effect on and can help fight unwanted Microorganisms can be used practically. The active ingredients are for use as pesticides suitable, especially as fungicides.
Fungizide Mittel im Pflanzenschutz werden eingesetzt zur Bekämpfung von Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.Fungicides in crop protection are used for Control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
Beispielhaft, aber nicht begrenzend seien einige Erreger von pilzlichen Erkrankungen, die unter die oben aufgezählten Oberbegriffe fallen, genannt:Some pathogens are exemplary but not limiting of fungal diseases listed below Generic terms fall, called:
Pythium-Arten, wie beispielsweise Pythium ultimum;
Phytophthora-Arten, wie beispielsweise Phytophthora infestans;
Pseudoperonospora-Arten, wie beispielsweise
Pseudoperonospora humuli oder Pseudoperonospora cubensis;
Plasmopara-Arten, wie beispielsweise Plasmopara viticola;
Peronospora-Arten, wie beispielsweise Peronospora pisi
oder P. brassicae;
Erysiphe-Arten, wie beispielsweise Erysiphe graminis;
Sphaerotheca-Arten, wie beispielsweise Sphaerotheca fuliginea;
Podosphaere-Arten, wie beispielsweise Podosphaera leucotricha;
Venturia-Arten, wie beispielsweise Venturia inaequalis;
Pyrenophora-Arten, wie beispielsweise Pyrenophora teres oder P. graminea
(Konidienform: Drechslera, Syn: Helminthosporium);
Cochliobolus-Arten, wie beispielsweise Cochliobolus sativus
(Konidienform: Drechslera, Syn: Helminthosporium);
Uromyces-Arten, wie beispielsweise Uromyces appendiculatus;
Puccinia-Arten, wie beispielsweise Puccinia recondita;
Tilletia-Arten, wie beispielsweise Tilletia caries;
Ustilago-Arten, wie beispielsweise Ustilago nuda oder Ustilago avenae;
Pellicularia-Arten, wie beispielsweise Pellicularia sasakii;
Pyricularia-Arten, wie beispielsweise Pyricularia oryzae;
Fuarium-Arten, wie beispielsweise Fusarium culmorum;
Botrytis-Arten, wie beispielsweise Botrytis cinerea;
Septoria-Arten, wie beispielsweise Septoria nodorum;
Leptosphaeria-Arten, wie beispielsweise Leptosphaeria nodorum;
Cercospora-Arten, wie beispielsweise Cercospora canescens;
Alternaria-Arten, wie beispielsweise Alternaria brassicae;
Pseudocercosporella-Arten, wie beispielsweise
Pseudocercosporella herpotrichoides.
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaere species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fuarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.
Die gute Pflanzenverträglichkeit der Wirkstoffe in den zur Bekämpfung von Pflanzenkrankheiten notwendigen Konzentrationen erlaubt eine Behandlung von oberirdischen Pflanzenteilen, von Pflanz- und Saatgut, und des Bodens.The good plant tolerance of the active ingredients in the concentrations necessary to combat plant diseases allows treatment from above ground Parts of plants, of seedlings, and des Floor.
Die erfindungsgemäßen Wirkstoffe zeigen insbesondere hervorragende Wirkung gegen Venturia-Arten im Obstbau, wie z. B. bei Äpfeln, und gegen Pyricularia-Arten in Reis.The active compounds according to the invention show in particular excellent effect against Venturia species in fruit growing, such as B. in apples, and against Pyricularia species in Rice.
Einige der erfindungsgemäßen Verbindungen der Formel (I) zeigen auch bakterizide Wirkung sowie Wirkung gegen Akariden und Insekten in Pflanzenkulturen wie auch gegen Hygiene- und Vorratsschädlinge.Some of the compounds of the formula (I) according to the invention also show bactericidal activity as well as activity against Acarids and insects in plant crops as well as against Hygiene and storage pests.
Die Wirkstoffe können in Abhängigkeit von ihren jeweiligen physikalischen und/oder chemischen Eigenschaften in übliche Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Wirkstoff-imprägnierte Natur- und synthetische Stoffe, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, ferner in Formulierungen mit Brennsätzen, wie Räucherpatronen, -dosen, -spiralen u. ä., sowie ULV-Kalt- und Warmnebel-Formulierungen.The active ingredients can depend on their respective physical and / or chemical properties in usual formulations are transferred, such as solutions, Emulsions, suspensions, powders, foams, pastes, granules, Aerosols, active ingredient-impregnated natural and synthetic Substances, very fine encapsulations in polymers Substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, -spirals u. Ä., and ULV cold and warm fog formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Ether und Ester, Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser; mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgase, wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid; als feste Trägerstoffe kommen in Frage: z. B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; als feste Trägerstoffe für Granulate kommen in Frage: z. B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengel; als Emulgier und/oder schaumerzeugende Mittel kommen in Frage: z. B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen- Fettalkohol-Ether, z. B. Alkylarylpolyglykol- Ether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z. B. Lignin-Sulfitablaugen und Methylcellulose.These formulations are prepared in a known manner e.g. B. by mixing the active ingredients with extenders, i.e. liquid solvents, under pressure liquefied gases and / or solid carriers, optionally using surfactants Agents, ie emulsifiers and / or dispersants and / or foam-generating agents. In case of Use of water as an extender can e.g. Belly organic solvents used as auxiliary solvents will. Essentially come as liquid solvents in question: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic Hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, Alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, Methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, as well as water; with liquefied gaseous Extenders or carriers are such liquids meant, which at normal temperature and below Normal pressure are gaseous, e.g. B. aerosol propellants, such as Halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; come as solid carriers in question: e.g. B. natural stone powder, such as kaolins, Clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as finely divided silica, aluminum oxide and silicates; come in as solid carriers for granules Question: e.g. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well synthetic granules from inorganic and organic Flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as an emulsifier and / or foam-generating agent come into question: z. B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene Fatty alcohol ethers, e.g. B. alkylaryl polyglycol Ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and Protein hydrolyzates; as dispersants are: e.g. B. lignin sulfite and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used, such as Gum arabic, polyvinyl alcohol, polyvinyl acetate, as well natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives can mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. B. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90%.The formulations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffe können in den Formulierungen in Mischung mit anderen bekannten Wirkstoffen vorliegen wie Fungizide, Insektizide, Akarizide und Herbizide sowie in Mischungen mit Düngemitteln und Wachstumsregulatoren. The active compounds according to the invention can be used in the formulations in a mixture with other known active ingredients are present such as fungicides, insecticides, acaricides and herbicides as well as in mixtures with fertilizers and growth regulators.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen wie gebrauchsfertige Lösungen, Suspensionen, Spritzpulver, Pasten, lösliche Pulver, Stäubemittel und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z. B. durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstäuben, Verschäumen, Bestreichen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low- Volume-Verfahren auszubringen oder die Wirkstoffzubereitung oder den Wirkstoff selbst in den Boden zu injizieren. Es kann auch das Saatgut der Pflanzen behandelt werden.The active ingredients as such, in the form of their formulations or the application forms prepared from it such as ready-to-use solutions, suspensions, wettable powders, Pastes, soluble powders, dusts and granules be applied. The application is done in the usual way Way, e.g. B. by pouring, spraying, spraying, scattering, Dusting, foaming, brushing, etc. It it is also possible to use the active ingredients according to the ultra-low Apply volume procedure or drug preparation or inject the active ingredient into the soil yourself. It can also treat the seeds of the plants will.
Bei der Behandlung von Pflanzenteilen können die Wirkstoffkonzentrationen in den Anwendungsformen in einem größeren Bereich variiert werden. Sie liegen im allgemeinen zwischen 1 und 0,0001 Gew.-%, vorzugsweise zwischen 0,5 und 0,001%.When treating parts of plants, the drug concentrations can in the application forms in one larger range can be varied. They generally lie between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
Bei der Saatgutbehandlung werden im allgemeinen Wirkstoffmengen von 0,001 bis 50 g je Kilogramm Saatgut, vorzugsweise 0,01 bis 10 g, benötigt.When treating seeds, amounts of active ingredient are generally used from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g.
Bei Behandlung des Bodens sind Wirkstoffkonzentrationen von 0,00001 bis 0,1 Gew.-%, vorzugsweise von 0,0001 bis 0,02%, am Wirkungsort erforderlich. When treating the soil are active ingredient concentrations from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02%, required at the site of action.
In den folgenden Anwendungsbeispielen werden die nachstehend aufgeführten Verbindungen als Vergleichssubstanzen eingesetzt:In the following application examples, the following are Compounds listed as reference substances used:
Zink-ethylen-1,2-bis-dithiocarbamidat (Zineb) (bekannt aus Phytopathology 33 [1943], 1113).Zinc-ethylene-1,2-bis-dithiocarbamidate (Zineb) (known from Phytopathology 33 [1943], 1113).
N,N-Dimethyl-N′-phenyl-N′-fluordichlormethylthiosulfamid (Dichlofluanid) (bekannt aus DE-AS 11 93 498). N, N-dimethyl-N'-phenyl-N'-fluorodichloromethylthiosulfamide (Dichlofluanide) (known from DE-AS 11 93 498).
Lösungsmittel: 12,5 Gewichtsteile Aceton
Emulgator: 0,3 Gewichtsteile AlkylarylpolyglykoletherSolvent: 12.5 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser und der angegebenen Menge Emulgator auf die gewünschte Konzentration.For the preparation of a suitable active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amount of solvent and dilute the concentrate with Water and the specified amount of emulsifier to the desired Concentration.
Zur Prüfung auf protektive Wirksamkeit bespritzt man junge Reispflanzen mit der Wirkstoffzubereitung bis zur Tropfnässe. Nach dem Abtrocknen des Spritzbelages werden die Pflanzen mit einer wäßrigen Sporensuspension von Pyricularia oryzae inokuliert. Anschließend werden die Pflanzen in einem Gewächshaus bei 100% rel. Luftfeuchtigkeit und 25°C aufgestellt.To test for protective efficacy one splashes young rice plants with the active ingredient preparation up to Dripping wet. After the spray coating has dried off the plants with an aqueous spore suspension of Pyricularia oryzae inoculated. Then the Plant in a greenhouse at 100% rel. humidity and set up at 25 ° C.
4 Tage nach der Inokulation erfolgt die Auswertung des Krankheitsbefalls.The evaluation of the Disease.
In diesem Test zeigen z. B. die in Tabelle 1 als Beispiele Nr. (2), (3), (6), (13), (26), (61), (62) und (83) aufgeführte erfindungsgemäßen Verbindungen erheblich bessere Wirkung als die Vergleichssubstanz (A). In this test, e.g. B. those in Table 1 as examples Nos. (2), (3), (6), (13), (26), (61), (62) and (83) listed compounds of the invention considerably better effect than the comparison substance (A).
Lösungsmittel: 4,7 Gewichtsteile Aceton
Emulgator: 0,3 Gewichtsteile AlkylarylpolyglycoletherSolvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.For the preparation of a suitable active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amounts of solvent and emulsifier and dilute that Concentrate with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit bespritzt man junge Pflanzen mit der Wirkstoffzubereitung bis zur Tropfnässe. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer wäßrigen Konidiensuspension des Apfelschorferregers (Venturia inaequalis) inokuliert und verbleiben dann 1 Tag bei 20°C und 100% relativer Luftfeuchtigkeit in einer Inkubationskabine.To test for protective efficacy one splashes young plants with the active ingredient preparation up to Dripping wet. After the spray coating has dried on, the Plants with an aqueous conidia suspension of Apple scab pathogen (Venturia inaequalis) inoculated and then remain at 20 ° C and 100% relative for 1 day Humidity in an incubation cabin.
Die Pflanzen werden dann im Gewächshaus bei 20°C und einer relativen Luftfeuchtigkeit von ca. 70% aufgestellt.The plants are then in the greenhouse at 20 ° C and a relative humidity of approx. 70%.
12 Tage nach der Inokulation erfolgt die Auswertung.Evaluation is carried out 12 days after the inoculation.
In diesem Test zeigen z. B. die in Tabelle 1 als Beispiele Nr. (9), (28), (38) und (61) aufgeführten Verbindungen erheblich bessere Wirkung als die Vergleichssubstanz (B). In this test, e.g. B. those in Table 1 as examples Nos. (9), (28), (38) and (61) listed compounds significantly better effect than the comparison substance (B).
9,4 g (0,05 Mol) Thiophosphorsäure-chlorid-0,0-diethylester, gelöst in 150 ml Acetonitril, werden bei 20°C unter Rühren zu einer Mischung aus 9,8 g (0,05 Mol) N- (3-Nitro-phenyl)-cyanamid, 7 g (0,0625 Mol) Kalium-tert- butylat und 150 ml Acetonitril tropfenweise gegeben. Das Reaktionsgemisch wird 12 Stunden bei 20°C gerührt und anschließend eingeengt. Der Rückstand wird in 200 ml Methylenchlorid aufgenommen, zweimal mit je 200 ml Wasser gewaschen, mit natriumsulfat getrocknet und filtriert. Vom Filtrat wird das Lösungsmittel bei leicht erhöhter Temperatur und unter vermindertem Druck sorgfältig abdestilliert.9.4 g (0.05 mol) of thiophosphoric acid chloride 0.0 diethyl ester, dissolved in 150 ml of acetonitrile, at 20 ° C. with stirring to a mixture of 9.8 g (0.05 mol) of N- (3-nitro-phenyl) cyanamide, 7 g (0.0625 mol) potassium tert- Butylate and 150 ml of acetonitrile added dropwise. The The reaction mixture is stirred at 20 ° C. for 12 hours then concentrated. The residue is dissolved in 200 ml of methylene chloride added, twice with 200 ml of water washed, dried with sodium sulfate and filtered. The solvent is slightly increased from the filtrate Temperature and distilled off carefully under reduced pressure.
Man erhält 14,5 g (92% der Theorie) N-(3-Nitrophenyl)- N-(diethoxythiophosphoryl)-cyanamid als braunen, öligen Rückstand vom Brechungsindex = 1,5863. 14.5 g (92% of theory) of N- (3-nitrophenyl) - N- (diethoxythiophosphoryl) cyanamide as a brown, oily Refractive index residue = 1.5863.
Analog zum Herstellungsbeispiel 1 - welches zur als Beispiel Nr. 74 in Tabelle 1 aufgeführten Verbindung führt - können auch die in Tabelle 1 als Beispiele Nr. 70 bis 73 und Nr. 75 bis 93 aufgeführten neuen Verbindungen der Formel (Ia) hergestellt werden.Analogous to production example 1 - which as an example No. 74 compound listed in Table 1 leads - can also use the example 1 in Table 1. 70 to 73 and No. 75 to 93 new compounds listed of the formula (Ia).
Auf prinzipiell gleiche Weise erhält man auch die weitgehend bekannten, als weitere Beispiele in Tabelle 1 aufgeführten Verbindungen der Formel (I).In a basically the same way, you also get them largely known as further examples in Table 1 listed compounds of formula (I).
Claims (10)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873717815 DE3717815A1 (en) | 1987-05-27 | 1987-05-27 | Fungicidal compositions based on substituted cyanamides |
JP63124041A JPS63307851A (en) | 1987-05-27 | 1988-05-23 | Bactericidal fungicide of substituted cyanamides |
KR1019880006231A KR880013451A (en) | 1987-05-27 | 1988-05-27 | Fungicides based on substituted cyanamides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873717815 DE3717815A1 (en) | 1987-05-27 | 1987-05-27 | Fungicidal compositions based on substituted cyanamides |
Publications (1)
Publication Number | Publication Date |
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DE3717815A1 true DE3717815A1 (en) | 1988-12-15 |
Family
ID=6328505
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19873717815 Withdrawn DE3717815A1 (en) | 1987-05-27 | 1987-05-27 | Fungicidal compositions based on substituted cyanamides |
Country Status (3)
Country | Link |
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JP (1) | JPS63307851A (en) |
KR (1) | KR880013451A (en) |
DE (1) | DE3717815A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2226815A (en) * | 1989-01-06 | 1990-07-11 | Shell Int Research | Fungicidal n-acyl cyanamides |
WO2001004100A1 (en) * | 1999-07-13 | 2001-01-18 | Lonza Ag | Process for preparing 2-amino-4-(4-fluorphenyl)-6-alkylpyrimidine-5-carboxylate |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6586617B1 (en) | 1999-04-28 | 2003-07-01 | Sumitomo Chemical Takeda Agro Company, Limited | Sulfonamide derivatives |
JP2001026506A (en) * | 1999-04-28 | 2001-01-30 | Takeda Chem Ind Ltd | Sulfonamide derivative |
US6476589B2 (en) | 2001-04-06 | 2002-11-05 | Linear Technology Corporation | Circuits and methods for synchronizing non-constant frequency switching regulators with a phase locked loop |
-
1987
- 1987-05-27 DE DE19873717815 patent/DE3717815A1/en not_active Withdrawn
-
1988
- 1988-05-23 JP JP63124041A patent/JPS63307851A/en active Pending
- 1988-05-27 KR KR1019880006231A patent/KR880013451A/en not_active Application Discontinuation
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2226815A (en) * | 1989-01-06 | 1990-07-11 | Shell Int Research | Fungicidal n-acyl cyanamides |
WO2001004100A1 (en) * | 1999-07-13 | 2001-01-18 | Lonza Ag | Process for preparing 2-amino-4-(4-fluorphenyl)-6-alkylpyrimidine-5-carboxylate |
US6579984B1 (en) | 1999-07-13 | 2003-06-17 | Lonza Ag | Process for preparing 2-amino-4-(4-fluorphenyl)-6-alkylpyrimidine-5-carboxylate |
CZ304307B6 (en) * | 1999-07-13 | 2014-02-26 | Lonza Ag | Process for preparing 2-amino-4-(4-fluorophenyl)-6-alkyl-pyrimidine-5-carboxylate |
Also Published As
Publication number | Publication date |
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JPS63307851A (en) | 1988-12-15 |
KR880013451A (en) | 1988-12-21 |
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