CS208757B2 - Fungicide means and method of making the active substances - Google Patents

Fungicide means and method of making the active substances Download PDF

Info

Publication number: CS208757B2
Authority: CS; Czechoslovakia
Prior art keywords: imino; alkyl; hexahydropyrimidine; carbon atoms; formula
Prior art date: 1977-10-18

Application number

CS786730A

Other languages

Czech (cs)

English (en)

Inventor

Hendrik Dolman

Johannes Kuipers

Original Assignee

Philips Nv

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

1977-10-18

Filing date

1978-10-16

Publication date

1981-09-15

1978-10-16 Application filed by Philips Nv filed Critical Philips Nv

1981-09-15 Publication of CS208757B2 publication Critical patent/CS208757B2/cs

Links

230000000855 fungicidal effect Effects 0.000 title claims abstract description 7
239000013543 active substance Substances 0.000 title abstract description 13
239000000417 fungicide Substances 0.000 title abstract description 6
238000004519 manufacturing process Methods 0.000 title description 2
-1 bezyloxy Chemical group 0.000 claims abstract description 104
150000001875 compounds Chemical class 0.000 claims abstract description 69
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 41
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
239000000203 mixture Substances 0.000 claims abstract description 35
125000000217 alkyl group Chemical group 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 27
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 15
229910052736 halogen Inorganic materials 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 7
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
150000002367 halogens Chemical group 0.000 claims abstract 6
239000004480 active ingredient Substances 0.000 claims description 17
239000007788 liquid Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
238000007363 ring formation reaction Methods 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
238000003776 cleavage reaction Methods 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
OKOVDKPGUFVBLG-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound C1CCCCC1C1=CC=C(N=C2NCCCN2)C=C1 OKOVDKPGUFVBLG-UHFFFAOYSA-N 0.000 abstract description 21
241000221577 Uromyces appendiculatus Species 0.000 abstract description 14
RAPKGLIUATVNTP-UHFFFAOYSA-N n-(4-hexylphenyl)-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound C1=CC(CCCCCC)=CC=C1N=C1NCCCN1 RAPKGLIUATVNTP-UHFFFAOYSA-N 0.000 abstract description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 3
238000003898 horticulture Methods 0.000 abstract description 2
150000002461 imidazolidines Chemical class 0.000 abstract description 2
241000540505 Puccinia dispersa f. sp. tritici Species 0.000 abstract 1
125000001589 carboacyl group Chemical group 0.000 abstract 1
208000015181 infectious disease Diseases 0.000 abstract 1
150000003751 zinc Chemical class 0.000 abstract 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
PEHDFSFYZKSKGH-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound NC1=NCCCN1 PEHDFSFYZKSKGH-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 21
DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical compound NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000003921 oil Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
241001480061 Blumeria graminis Species 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
241001123569 Puccinia recondita Species 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
125000005843 halogen group Chemical group 0.000 description 8
241000209140 Triticum Species 0.000 description 7
239000008187 granular material Substances 0.000 description 7
DNWWODFFEFZASF-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1NC1=CC=C(C2CCCCC2)C=C1 DNWWODFFEFZASF-UHFFFAOYSA-N 0.000 description 7
241000221785 Erysiphales Species 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
244000141359 Malus pumila Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
235000021307 Triticum Nutrition 0.000 description 6
239000007900 aqueous suspension Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
238000005507 spraying Methods 0.000 description 6
NJBCAMIMVVABJG-UHFFFAOYSA-N 2-(4-octylphenyl)-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound C(CCCCCCC)C1=CC=C(C=C1)C1NCCC(N1)=N NJBCAMIMVVABJG-UHFFFAOYSA-N 0.000 description 5
235000011430 Malus pumila Nutrition 0.000 description 5
235000015103 Malus silvestris Nutrition 0.000 description 5
XTLGPJLVHVUKOU-UHFFFAOYSA-N S(=O)(=O)(O)O.C1(CCCCC1)C1=CC=C(C=C1)C1NCCC(N1)=N Chemical compound S(=O)(=O)(O)O.C1(CCCCC1)C1=CC=C(C=C1)C1NCCC(N1)=N XTLGPJLVHVUKOU-UHFFFAOYSA-N 0.000 description 5
244000038559 crop plants Species 0.000 description 5
230000000694 effects Effects 0.000 description 5
CIYMQQLOODPCEE-UHFFFAOYSA-N n-(4-butylphenyl)-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound C1=CC(CCCC)=CC=C1N=C1NCCCN1 CIYMQQLOODPCEE-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
RPSKYLBBPNSUDV-UHFFFAOYSA-N C1(CCCCC1)C1=CC=C(C=C1)C1NCC(C(N1)C)=N Chemical compound C1(CCCCC1)C1=CC=C(C=C1)C1NCC(C(N1)C)=N RPSKYLBBPNSUDV-UHFFFAOYSA-N 0.000 description 4
240000005979 Hordeum vulgare Species 0.000 description 4
HAVMZVNXCGMGBL-UHFFFAOYSA-N N=C1NC(C2=CC=C(CCC3=CC=CC=C3)C=C2)NCC1 Chemical compound N=C1NC(C2=CC=C(CCC3=CC=CC=C3)C=C2)NCC1 HAVMZVNXCGMGBL-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
241001337928 Podosphaera leucotricha Species 0.000 description 4
241001123583 Puccinia striiformis Species 0.000 description 4
229940114081 cinnamate Drugs 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000011534 incubation Methods 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000003495 polar organic solvent Substances 0.000 description 4
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical class C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 3
FCVKQASWJVBEFI-UHFFFAOYSA-N 2-(4-heptylphenyl)-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound C(CCCCCC)C1=CC=C(C=C1)C1NCCC(N1)=N FCVKQASWJVBEFI-UHFFFAOYSA-N 0.000 description 3
XSJDIGYQRHMGMM-UHFFFAOYSA-N 2-(4-octylphenyl)-2,5-dihydro-1H-imidazol-4-amine Chemical compound C(CCCCCCC)C1=CC=C(C=C1)C1NCC(N1)=N XSJDIGYQRHMGMM-UHFFFAOYSA-N 0.000 description 3
LKCQEXMAHZFZTN-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)sulfanylphenyl]-2,5-dihydro-1H-imidazol-4-amine Chemical compound C1=CC(Cl)=CC=C1SC1=CC=C(C2NC(=N)CN2)C=C1 LKCQEXMAHZFZTN-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
QRMHNUUUOMZKHT-UHFFFAOYSA-N C(C(C)C)C1=CC=C(C=C1)C1NCCC(N1)=N Chemical compound C(C(C)C)C1=CC=C(C=C1)C1NCCC(N1)=N QRMHNUUUOMZKHT-UHFFFAOYSA-N 0.000 description 3
PUIVKQNPVCYILN-UHFFFAOYSA-N C(CCCCC)SC1=CC=C(C=C1)C1NCC(N1)=N Chemical compound C(CCCCC)SC1=CC=C(C=C1)C1NCC(N1)=N PUIVKQNPVCYILN-UHFFFAOYSA-N 0.000 description 3
NPJKWZHDBMJXLR-UHFFFAOYSA-N CCCCCCC1=CSC(=C1)C2NCCC(=N2)N Chemical compound CCCCCCC1=CSC(=C1)C2NCCC(=N2)N NPJKWZHDBMJXLR-UHFFFAOYSA-N 0.000 description 3
NWYWJRRWILECHY-UHFFFAOYSA-N CCCCCCCCCCC1=CC=C(C=C1)C2NCCC(=N2)N Chemical compound CCCCCCCCCCC1=CC=C(C=C1)C2NCCC(=N2)N NWYWJRRWILECHY-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229920003171 Poly (ethylene oxide) Chemical class 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
FYCACPIHZVZRKB-UHFFFAOYSA-L [Cl-].[Zn+2].C(CCCCCCC)C1=CC=C(C=C1)C1NCCC(N1)=N.[Cl-] Chemical compound [Cl-].[Zn+2].C(CCCCCCC)C1=CC=C(C=C1)C1NCCC(N1)=N.[Cl-] FYCACPIHZVZRKB-UHFFFAOYSA-L 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000012876 carrier material Substances 0.000 description 3
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244000053095 fungal pathogen Species 0.000 description 3
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238000002844 melting Methods 0.000 description 3
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239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
150000003009 phosphonic acids Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
150000003460 sulfonic acids Chemical class 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
URUNMPPKCQLYED-UHFFFAOYSA-N 2-(4-benzylphenyl)-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound C(C1=CC=CC=C1)C1=CC=C(C=C1)C1NCCC(N1)=N URUNMPPKCQLYED-UHFFFAOYSA-N 0.000 description 2
SKKXCFRUMVWLCI-UHFFFAOYSA-N 2-(4-hexylphenyl)-2,5-dihydro-1H-imidazol-4-amine Chemical compound C(CCCCC)C1=CC=C(C=C1)C1NCC(N1)=N SKKXCFRUMVWLCI-UHFFFAOYSA-N 0.000 description 2
PMWAERPBNDPNDV-UHFFFAOYSA-N 2-(4-nonylphenyl)-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound C(CCCCCCCC)C1=CC=C(C=C1)C1NCCC(N1)=N PMWAERPBNDPNDV-UHFFFAOYSA-N 0.000 description 2
JBYNMPPHOGQBOV-UHFFFAOYSA-N 2-(4-pentylphenyl)-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound C(CCCC)C1=CC=C(C=C1)C1NCCC(N1)=N JBYNMPPHOGQBOV-UHFFFAOYSA-N 0.000 description 2
RLMZNLCAHXJQCH-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)sulfanylphenyl]-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound ClC1=CC=C(C=C1)SC1=CC=C(C=C1)C1NCCC(N1)=N RLMZNLCAHXJQCH-UHFFFAOYSA-N 0.000 description 2
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BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000005286 illumination Methods 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
229940100892 mercury compound Drugs 0.000 description 1
150000002731 mercury compounds Chemical class 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 description 1
PQHDNVPBHAPWBC-UHFFFAOYSA-N n-(4-octylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(CCCCCCCC)=CC=C1N=C1NCCN1 PQHDNVPBHAPWBC-UHFFFAOYSA-N 0.000 description 1
PQOCOLUEWNOTPL-UHFFFAOYSA-N n-(4-octylthiophen-2-yl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound CCCCCCCCC1=CSC(N=C2NCCN2)=C1 PQOCOLUEWNOTPL-UHFFFAOYSA-N 0.000 description 1
FNSOYACTNQMLCT-UHFFFAOYSA-N n-phenyl-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound C1CCNC(NC=2C=CC=CC=2)=N1 FNSOYACTNQMLCT-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
150000003252 quinoxalines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000007873 sieving Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000002641 tar oil Substances 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/14—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to said nitrogen atoms
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Wood Science & Technology (AREA)
Dentistry (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS786730A 1977-10-18 1978-10-16 Fungicide means and method of making the active substances CS208757B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL7711390A NL7711390A (nl)	1977-10-18	1977-10-18	Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen.

Publications (1)

Publication Number	Publication Date
CS208757B2 true CS208757B2 (en)	1981-09-15

Family

ID=19829358

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CS786730A CS208757B2 (en)	1977-10-18	1978-10-16	Fungicide means and method of making the active substances
CS786730A CS208758B2 (en)	1977-10-18	1978-10-16	Metod of making the new 2-arylaminohexahydropyrimidins a-imidazolidins

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CS786730A CS208758B2 (en)	1977-10-18	1978-10-16	Metod of making the new 2-arylaminohexahydropyrimidins a-imidazolidins

Country Status (21)

Country	Link
US (2)	US4374143A (mo)
EP (1)	EP0001663B1 (mo)
JP (1)	JPS5463080A (mo)
AR (1)	AR225601A1 (mo)
AU (1)	AU521181B2 (mo)
CA (1)	CA1106845A (mo)
CS (2)	CS208757B2 (mo)
DD (2)	DD139989A5 (mo)
DE (1)	DE2861822D1 (mo)
DK (1)	DK458178A (mo)
EG (1)	EG13497A (mo)
ES (2)	ES474227A1 (mo)
HU (1)	HU178690B (mo)
IL (1)	IL55728A (mo)
IT (1)	IT1099744B (mo)
NL (1)	NL7711390A (mo)
NZ (1)	NZ188660A (mo)
PL (2)	PL120588B1 (mo)
SU (2)	SU895289A3 (mo)
TR (1)	TR20567A (mo)
ZA (1)	ZA785278B (mo)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7711390A (nl) *	1977-10-18	1979-04-20	Philips Nv	Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen.
US4321838A (en) *	1979-08-13	1982-03-30	Feldman Robert I	Power coupling for a chain saw
DE2933930A1 (de) *	1979-08-22	1981-03-12	C.H. Boehringer Sohn, 6507 Ingelheim	2-(2-chlor-4-cyclopropyl-phenylimino)-imidazolidin, dessen saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben.
US4647557A (en) *	1982-12-28	1987-03-03	Gerard Moinet	Novel heterocyclic derivatives bearing an amino radical, processes for their production and the pharmaceutical compositions containing them
GB8922750D0 (en) *	1989-10-10	1989-11-22	Dow Chemical Co	Fungicidal compounds,their production and use
US5292743A (en) *	1989-10-10	1994-03-08	Dowelanco	Fungicidal compositions, fungicidal compounds, their production and use
GB9016800D0 (en) *	1990-07-31	1990-09-12	Shell Int Research	Tetrahydropyrimidine derivatives
US5866579A (en) *	1997-04-11	1999-02-02	Synaptic Pharmaceutical Corporation	Imidazole and imidazoline derivatives and uses thereof
NZ331480A (en) *	1997-09-04	2000-02-28	F	2-(Arylphenyl)amino-imidazoline derivatives and pharmaceutical compositions
US6184242B1 (en)	1997-09-04	2001-02-06	Syntex Usa (Llc)	2-(substituted-phenyl)amino-imidazoline derivatives
JP2001354659A (ja) *	2000-06-13	2001-12-25	Kureha Chem Ind Co Ltd	新規ピラゾリン誘導体、その製造方法、及び有害生物防除剤
US6417186B1 (en)	2000-11-14	2002-07-09	Syntex (U.S.A.) Llc	Substituted-phenyl ketone derivatives as IP antagonists
CA2522817A1 (en) *	2003-05-01	2004-11-11	F. Hoffmann-La Roche Ag	Imidazolin-2-ylaminophenyl amides as ip antagonists
KR100768609B1 (ko) *	2003-07-09	2007-10-18	에프. 호프만-라 로슈 아게	티오페닐아미노이미다졸린
JP2007308392A (ja) *	2006-05-16	2007-11-29	Bayer Cropscience Ag	殺虫性ベンズアミジン類
WO2016043260A1 (ja) *	2014-09-19	2016-03-24	塩野義製薬株式会社	環状グアニジンまたはアミジン化合物

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2899434A (en) *		1959-08-11		Z-phenylamino-l
US2899426A (en) *		1959-08-11		Synthesis of l
FR1211341A (fr) *	1955-12-19	1960-03-15	A Wander Dr	Procédé pour la préparation de 2-amino-imidazolines
US3202660A (en) *	1961-10-09	1965-08-24	Boehringer Sohn Ingelheim	Process for the preparation of 3-arylamino-1, 3-diazacycloalkenes
US3236857A (en) *	1961-10-09	1966-02-22	Boehringer Sohn Ingelheim	2-(phenyl-amino)-1, 3-diazacyclopentene-(2) substitution products
BE632578A (mo) *	1963-05-22
DE1670274A1 (de) *	1966-10-31	1970-07-16	Boehringer Sohn Ingelheim	Neues Verfahren zur Herstellung von 2-Arylamino-1,3-diazacycloalkenen-(2)
US3882229A (en) *	1972-07-21	1975-05-06	Nordmark Werke Gmbh	Composition and method for shrinking mucous membranes
DE2316377C3 (de) *	1973-04-02	1978-11-02	Lentia Gmbh, Chem. U. Pharm. Erzeugnisse - Industriebedarf, 8000 Muenchen	Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen
AT330769B (de) *	1974-04-05	1976-07-26	Chemie Linz Ag	Verfahren zur herstellung von 2-arylamino- 2-imidazolin-derivaten und ihren salzen
DE2542702C2 (de) *	1975-09-25	1983-11-10	Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München	Verfahren zur Herstellung von 1-Benzoyl-2-(2,6-dichlorphenylamino)-2-imidazolin
NL7711390A (nl) *	1977-10-18	1979-04-20	Philips Nv	Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen.
US4262005A (en) *	1978-05-31	1981-04-14	The Boots Company Limited	Compounds, compositions and methods for controlling pests
DE2933930A1 (de) *	1979-08-22	1981-03-12	C.H. Boehringer Sohn, 6507 Ingelheim	2-(2-chlor-4-cyclopropyl-phenylimino)-imidazolidin, dessen saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben.

1977
- 1977-10-18 NL NL7711390A patent/NL7711390A/xx not_active Application Discontinuation
1978
- 1978-09-18 ZA ZA785278A patent/ZA785278B/xx unknown
- 1978-09-27 AR AR273866A patent/AR225601A1/es active
- 1978-10-13 HU HU78PI643A patent/HU178690B/hu unknown
- 1978-10-13 CA CA313,362A patent/CA1106845A/en not_active Expired
- 1978-10-13 IL IL55728A patent/IL55728A/xx unknown
- 1978-10-13 DK DK458178A patent/DK458178A/da not_active Application Discontinuation
- 1978-10-13 IT IT28761/78A patent/IT1099744B/it active
- 1978-10-16 CS CS786730A patent/CS208757B2/cs unknown
- 1978-10-16 DE DE7878200241T patent/DE2861822D1/de not_active Expired
- 1978-10-16 AU AU40754/78A patent/AU521181B2/en not_active Expired
- 1978-10-16 PL PL1978210324A patent/PL120588B1/pl unknown
- 1978-10-16 PL PL21699678A patent/PL216996A1/xx unknown
- 1978-10-16 NZ NZ188660A patent/NZ188660A/xx unknown
- 1978-10-16 TR TR20567A patent/TR20567A/xx unknown
- 1978-10-16 DD DD78208481A patent/DD139989A5/de unknown
- 1978-10-16 JP JP12724678A patent/JPS5463080A/ja active Granted
- 1978-10-16 CS CS786730A patent/CS208758B2/cs unknown
- 1978-10-16 DD DD78217704A patent/DD147846A5/de unknown
- 1978-10-16 EP EP78200241A patent/EP0001663B1/en not_active Expired
- 1978-10-16 ES ES474227A patent/ES474227A1/es not_active Expired
- 1978-10-17 EG EG606/78A patent/EG13497A/xx active
1979
- 1979-03-21 SU SU792739504A patent/SU895289A3/ru active
- 1979-05-02 ES ES480166A patent/ES480166A1/es not_active Expired
1980
- 1980-02-28 SU SU802891001A patent/SU969160A3/ru active
1981
- 1981-05-18 US US06/264,460 patent/US4374143A/en not_active Expired - Fee Related
- 1981-05-18 US US06/264,461 patent/US4396617A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IT7828761A0 (it)	1978-10-13
SU895289A3 (ru)	1981-12-30
JPS5463080A (en)	1979-05-21
NL7711390A (nl)	1979-04-20
EG13497A (en)	1982-06-30
NZ188660A (en)	1980-03-05
IT1099744B (it)	1985-09-28
IL55728A (en)	1982-05-31
EP0001663A1 (en)	1979-05-02
DE2861822D1 (en)	1982-07-01
JPS6141353B2 (mo)	1986-09-13
DK458178A (da)	1979-04-19
CS208758B2 (en)	1981-09-15
PL120588B1 (en)	1982-03-31
AU521181B2 (en)	1982-03-18
HU178690B (en)	1982-06-28
EP0001663B1 (en)	1982-05-12
AR225601A1 (es)	1982-04-15
PL216996A1 (mo)	1980-07-14
TR20567A (tr)	1982-01-01
ES474227A1 (es)	1979-10-16
ES480166A1 (es)	1979-12-16
US4396617A (en)	1983-08-02
DD139989A5 (de)	1980-02-06
PL210324A1 (mo)	1980-03-10
SU969160A3 (ru)	1982-10-23
DD147846A5 (de)	1981-04-22
ZA785278B (en)	1980-05-28
US4374143A (en)	1983-02-15
AU4075478A (en)	1980-04-24
IL55728A0 (en)	1978-12-17
CA1106845A (en)	1981-08-11

Publication	Publication Date	Title
HU186379B (en)	1985-07-29	Compoisitons for kiling tree-louse, containing new sulphonyl derivatives as active substances and process for preparing the active substance
CZ281586B6 (cs)	1996-11-13	Derivát 2-anilinopyrimidinu, způsob jeho přípravy a fungicidní prostředek, který ho obsahuje
EP0001663B1 (en)	1982-05-12	Novel 2-arylamino-hexahydropyrimidines and -imidazolidines, salts and complexes thereof, method of preparing the novel compounds and fungicidal compositions which contain the novel compounds
IL44710A (en)	1977-12-30	1-phenyl-2-azolyl-formamidines their preparation and their use as herbicides
JPS6097962A (ja)	1985-05-31	１−置換イミダゾ−ル−５−カルボン酸誘導体，それらの製造方法ならびにそれらを含有する殺菌剤，除草剤および植物生長調整剤
US4783459A (en)	1988-11-08	Anilinopyrimidine fungicides
KR900001910B1 (ko)	1990-03-26	1-디메틸카르바모일-3-치환-5-치환-1h-1,2,4-트리아졸 및 그의 제조방법
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