AU6507590A - Guanidines as fungicides - Google Patents
Guanidines as fungicidesInfo
- Publication number
- AU6507590A AU6507590A AU65075/90A AU6507590A AU6507590A AU 6507590 A AU6507590 A AU 6507590A AU 65075/90 A AU65075/90 A AU 65075/90A AU 6507590 A AU6507590 A AU 6507590A AU 6507590 A AU6507590 A AU 6507590A
- Authority
- AU
- Australia
- Prior art keywords
- formula
- compound
- group
- composition
- hydrogen
- 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.)
- Granted
Links
- 239000000417 fungicide Substances 0.000 title description 6
- 150000002357 guanidines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- -1 phenoxy, phenyl Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 230000000855 fungicidal effect Effects 0.000 claims description 8
- 241000233866 Fungi Species 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 230000002538 fungal effect Effects 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 206010061217 Infestation Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 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 2
- 239000003863 metallic catalyst Substances 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 244000052769 pathogen Species 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 231100000167 toxic agent Toxicity 0.000 description 7
- 239000003440 toxic substance Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000000361 pesticidal effect Effects 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000209219 Hordeum Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 229960004132 diethyl ether Drugs 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- DXTIKTAIYCJTII-UHFFFAOYSA-N guanidine acetate Chemical compound CC([O-])=O.NC([NH3+])=N DXTIKTAIYCJTII-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 2
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 241000223221 Fusarium oxysporum Species 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 241001123569 Puccinia recondita Species 0.000 description 2
- 241000520648 Pyrenophora teres Species 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
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- 241000894007 species Species 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- PYIVLZVGWKGCGG-UHFFFAOYSA-N 1-(4-tert-butylphenyl)propan-2-amine Chemical compound CC(N)CC1=CC=C(C(C)(C)C)C=C1 PYIVLZVGWKGCGG-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- WKCZSFRAGKIIKN-UHFFFAOYSA-N 2-(4-tert-butylphenyl)ethanamine Chemical compound CC(C)(C)C1=CC=C(CCN)C=C1 WKCZSFRAGKIIKN-UHFFFAOYSA-N 0.000 description 1
- RZVPFDOTMFYQHR-UHFFFAOYSA-N 2-chloro-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(Cl)=N1 RZVPFDOTMFYQHR-UHFFFAOYSA-N 0.000 description 1
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 1
- CLXSBHRRZNBTRT-VOTSOKGWSA-N 4-[(e)-2-phenylethenyl]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1\C=C\C1=CC=CC=C1 CLXSBHRRZNBTRT-VOTSOKGWSA-N 0.000 description 1
- KRNAJRBXIMJEFF-UHFFFAOYSA-N 4-hexylbenzaldehyde Chemical compound CCCCCCC1=CC=C(C=O)C=C1 KRNAJRBXIMJEFF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
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- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
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- 241000222122 Candida albicans Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 244000131522 Citrus pyriformis Species 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WDMJWWMDMSQIGM-UHFFFAOYSA-N n-(2-phenylethyl)butan-1-amine Chemical compound CCCCNCCC1=CC=CC=C1 WDMJWWMDMSQIGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 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
- 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
- A01N43/62—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms three- or four-membered rings or rings with more than six members
-
- 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
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
FUNGICIDAL COMPOSITIONS, FUNGICIDAL COMPOUNDS,
THEIR PRODUCTION AND USE
This invention relates to novel chemical compounds having fungicidal activity, and in particular to such compounds containing a guanidine group and to the use of these and other compounds as fungicides.
Certain substituted guanidines are disclosed without reference to antifungal activity in an article by Glushkov and Nikolaeva (Chem Abst. Vol 110, No. 212684r) and in Dutch Patent No. 6510117.
Many substituted guanidines are known to have
antifungal and antibacterial activity. A detailed review of the antifungal activity of such compounds is to be found in International Pest Control, November/December 1986, p.p.148-155 (H.R. Hudson, I.A.O. Ojo, and M. Pianka).
Fungicidally active compounds containing a guanidine- type grouping compounds are also disclosed, for example in U.S. Patent No. 2988478.
The present invention provides the use as a fungicide of compounds of the formula
wherein R1 and R7 are each independently
hydrogen or C1-C3 alkyl,
R2 is hydrogen or C1-C6 alkyl, R3 and R4
independently and each R5 independently are hydrogen or C1-C4 alkyl,
R6 is a cyclohexyl group or a monocyclic or bicyclic aromatic group (for example phenyl or
naphthalenyl) substituted with from 1 to 5 groups of the formula R8,
wherein R8 is halogen, a C1-C10 alkyl
group, preferably C3-C4 alkyl, more preferably
t-butyl, a C1-C10 alkoxy group, a trialkylsilyl
group, or a phenyl, phenoxy, phenyl C1-C2 alkylene, or phenyl alkenylene group, optionally substituted on the phenyl or phenoxy group with from 1 to 5 halogen atoms, C1-C6 alkyl or C1-C6 alkoxy groups,
trihalomethyl groups, phenyl groups or phenoxy groups, p is 0, 1 or 2
Y is a group of the formula -(CR9R9)n-,
wherein
n is 2, 3, or 4,
each R9 independently is hydrogen or C1-C4 alkyl, and X- is a suitable counter-ion. The invention also provides fungicidal compositions which contain such compounds, particularly together with an
agriculturally acceptable carrier or diluent.
A number of compounds of formula I-A, I-B and I-C are novel, particularly those wherein p is 1 or 2 and n is 3 or 4. Accordingly, the invention also provides such novel compounds.
It will of course be appreciated that although the compounds of formulae I-A, I-B and I-C are illustrated as containing simple double bonds, in practice
considerable delocalisation of the double bond
structure will take place over the three nitrogen atoms of the compound. The compounds of the invention contain three basic nitrogen atoms, and thus can exist either in the form of the free base (formulae I-B and I-C), or a salt (formula I-A), for example a quaternary salt or an acid addition salt. The compound can thus exist in tautomeric forms, all of which are within the scope of the present invention.
R1 and R7 are preferably each hydrogen, methyl or ethyl more preferably hydrogen, and R2 is
preferably hydrogen or methyl, more preferably
hydrogen.
Y is preferably a group of the formula
-(CR9R9)3-, wherein R9 is as defined above
(preferably hydrogen or methyl), more preferably a
group of the formula -(CH2)3-, or
-CHMeCH2CHMe-.
Each of groups R4 and R5 are preferably
hydrogen, group R3 is preferably methyl, and p is preferably 1.
The group R6 is preferably a substituted phenyl group, more preferably a 4-t- butylphenyl group or 4-trimethylsilylphenyl.
The ring containing the guanidine group is preferably six membered, i.e. n in the definition of Y is preferably 3.
The terms alkyl, alkoxy, alkylene, alkenylene and the like, as used herein, are intended to include within their scope both straight and branched groups, and the terms alkenyl, alkenylene and the like are intended to include groups containing one or more than one double bonds. The term halogen and halo as used herein include chlorine, bromine, fluorine and iodine. It will be appreciated that certain combinations of substituent groups for compounds which fall within the
definition of formula I-A, I-B and I-C given above will be impossible to prepare for steric and other chemical reasons. Such compounds are not included within the scope of the invention.
The anion X" in formula I-A may be any anion addition salt capable of forming an acid, for example chloride, bromide, acetate, stearate, benzoate or dodecylbenzenesulphonate, the chloride being
preferred.
The compounds of formula I-A, I-B and I-C may be prepared by reacting a compound of the formula
II
R6-(CR5R5)pCR3R4-NH
with a salt of the formula
III
wherein R1 to R6, Y, x and p are as defined above, and L is a suitable leaving group, for example an alkylthio group, preferably at a temperature of from 50 to 200ºC. The reaction may be carried out in a suitable organic solvent for example an alkanol such as
n-pentanol, or in the absence of solvent.
L is preferably an alkylthio gooup.
The compounds of formula I-A, I-B and I-C may also be prepared by reducing a compound of formula
preferably utilising hydrogen and a metallic catalyst.
The reaction may be carried out at atmospheric
temperature and pressure in a polar solvent, in the presence of an acid. The compound of formula V may be prepared by reacting a compound of the formula
II
R6- ( CR5R5 )pCR3R4-NH
with a compound of the formula
wherein R2 to R6 and each R9 independently, is as defined above, and L is a suitable leaving group. The reaction between compound II and compound III is preferably carried out in a polar solvent at a temperature of from 50 to 200ºC, in the presence of a base. Compounds of the formula II may generally be prepared by the reaction of a compound of the formula
Na+ R3R4CNO2- with a compound of the formula:
followed by reduction of the nitro group, preferably
employing a metal hydride such as LiA1H4, and when R2 is alkyl, alkylation with an alkylating agent, for example a haloalkane. Compound VI may be prepared according to Katrizky, de Ville and Patel (J.C.S. Chem. Comm. 1979, 602) from a compound of formula
R6-(CR5R5)p-NH2
and 2,4,6,-triphenylpyrilium tetrafluoroborate.
Alternatively and preferably, compounds of formula I-B, wherein certain of the R5 groups are restricted to hydrogen, may be prepared by the reaction of a compound of the formula
R3CH2NO2
with a compound of the formula
R6-(CR5R5)p-1CR5O
preferably in the presence of a mild base at a
temperature of from 25 to 150 °C, followed by reduction of the nitro group and the double bond. The reduction may be carried out, for example using a metal hydride such as LiA1E4, at a temperature of from -80 to
100ºC.
The compounds of formula I-A, I-B and I-C may be used as fungicides in particular for agricultural use, against a wide range of pathogens, for example
Ascomycetes, Eumycetes and Fungi Imperfecti, in a protectant or eradicant fashion, and exhibit low phytotoxcicity to crops, in particular cereal and broadleaf crops. In particular, the compounds in accordance with the invention may be applied to the roots, seeds, or foliage of barley and other plants, for the control of various fungi, without damaging their commercial value. In particular the compounds of the present invention effectively control a variety of undesirable fungi which infest useful plant crops.
Many of the compounds are particularly effective against members of the i) Deuteromycotina such as
Septoria nodorum (glume blotch of cereals), Pyricularia oryzae (rice-blast), Botrytis cinerea (grey mould of grapes and Fusarium Oxysporum (various wilt diseases), ii) Ascomycotina such as Pyrenophora teres (net-blotch) and Erysiphe graminis (powdery mildew), and iii)
Basidiomycotina such as Puccinia recondita (leaf rust).
The compounds can be applied to the seeds, roots or foliage of cereals or other plants and will kill or control the growth of various fungi without damaging the commercial value of the said plants.
Where the acid addition salt is employed, the improved water solubility (especially of the chloride) also allows the preparation of solutions (in water or organic solvents) in which, at use rate, the addition salt is completely soluble in the spray dilution.
At least utilising the preferred embodiments of the invention a single application of the compounds can provide a residual control of powdery mildew diseases over an extended period. Also, the compounds can be effective in eliminating established barley powdery mildew infestation. Furthermore, many
compounds have been found to be translocated in plants and, thus, can provide a systemic protection against powdery mildew.
The compounds of the invention may also find application as non-agricultural fungicides for example in medicine as antimycotics against organisms such as Candida albicans, Candida spp, Trichophyton spp,
Aspergillus spp, Microsporum spp and Sporothrix spp, and also as agents against parasites such as
Leishmania.
As indicated above, the invention includes within its scope fungicidal compositions comprising a
fungicidally effective amount of a compound of formula l-A, I-B or I-C together with an inert carrier or
diluent. Such compositions may be in the form of a liquid, powder, dust or granular composition containing one or more of the active compounds in and one or more inert, non-phytotoxic materials, known in the art as agricultural adjuvants and/or carriers, in solid or liquid form. Thus, for example, the active compound (s) can be admixed with one or more additives including water or other liquid carriers such as organic
solvents, and petroleum distillates, surface active dispersing agents, and finely divided inert solids.
In such compositions, the active ingredients are generally present in a concentration of from 2 per cent to about 95 per cent by weight preferably from 10 per cent to 95 per cent by weight and most advantageously 10 per cent to 75 per cent by weight. The compound can be employed in the form of a solution, a diluted flowable compositions or a wettable powder composition containing 2 to 10 , 000 ppm of active ingredient .
Preferably 10 to 600 ppm are employed.
When the carrier contains a surface active agent, from about 0.1 to about 20 per cent by weight of the active ingredient is advantageously employed.
Depending upon the concentration in the composition, such augmented compositions are adapted to be employed for the control of the undesirable fungi or employed as concentrates and subsequently diluted with additional inert carrier, e.g. water, to produce the ultimate treating compositions.
In general, good results can be obtained with liquid compositions containing from about 0.0001 to about 2.0 per cent by weight of the active compound in the final diluted form. With dusts, good results can usually be obtained with compositions containing from about 0.1 to about 2.0 per cent or more by weight of active compound. Where the compositions are to be
applied to foliage of plants, it is preferred that the toxicant be present in an amount not to exceed about 0.8 per cent in liquid compositions and about 1.0 per cent in dusts.
In terms of hectarage application, good controls of powdery mildews can be obtained when the active ingredients are applied to growing plants at a dosage of from about 0.004 to about 4 kg/hectare. When employed as fungicides for the treatment of seeds or non-living substrates, from about 0.1 to about 100 gram of active ingredient per kilogram of substrate is an effective dose.
In the preparation of dust, or wettable powder compositions, the toxicant products can be compounded with any of the finely divided solids, such as
prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, or the like. In such operations, the finely divided carrier is ground or mixed with the toxicant or wet with a solution of the toxicant in a volatile organic solvent. Also, such compositions when employed as concentrates can be dispersed in water, with or without the aid of dispersing agents to form spray mixtures. Dust
compositions are advantageously employed when treating seeds.
Granular formulations are usually prepared by impregnating a solution of the toxicant in a volatile organic solvent onto a bed of coarsely divided
attapulgite, bentonite, diatomite, or the like.
Similarly, the toxicant products can be compounded with a suitable water-immiscible inert organic liquid and a surface active dispersing agent to produce an emulsifiable concentrate which can be further diluted with water and oil to form spray mixtures in the form of oil-in-water emulsions which may optionally contain
water miscible organic co-solvents to improve the physical properties of the formulation. In such compositions, the carrier comprises an aqueous
emulsion, i.e., a mixture of inert water-immiscible solvent and optional water miscible organic co-solvent, emulsifying agent, and water.
Emulsifiers which can be advantageously employed herein can be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a blend of two or more emulsifiers. Examples of nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxide or mixtures of ethylene and propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or polyoxyalkylene.
Cationic emulsifiers include quaternary ammonium compounds and fatty amines. Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil soluble salts or
sulphated polyglycol ethers and appropriate salts of phosphated polyglycol ether.
Representative organic liquids which can be employed in preparing the emulsifiable concentrates of the present invention are the aromatic liquids such as xylene; propyl benzene fractions; or mixed naphthalene fractions; mineral oils substituted aromatic organic liquids such as dioctyl phthalate; kerosene; butene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol derivatives such as the n-butyl ether, ethyl ether or methyl ether of diethylene glycol, and the methyl ether of
triethylene glycol. Mixtures of two or more organic
liquids are also often suitably employed in the
preparation of the emulsifiable concentrate. The preferred organic liquids are xylene, and propyl benzene fractions, with xylene being most preferred . The surface active dispersing agents are usually employed in liquid compositions and in the amount of from 0.1 to 20 per cent by weight of the combined weight of the dispersing
agent and active compound. The active compositions can also contain other compatible additives, for example, plant growth regulators and other biologically active compounds used in agriculture.
In particular, the active compositions may contain adjuvant surfactants to enhance the deposition, wetting and penetration of the composition onto the target crop and organism. These adjuvant surfactants may
optionally be employed as a component of the
formulation or as a tank mix. The amount of adjuvant surfactant will vary from 0.01 per cent to 1.0 per cent v/v based on a spray-volume of water, preferably 0.05 to 0.5 per cent. Suitable adjuvant surfactants include ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or sulphosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines and blends of surfactants with mineral or vegetable oils.
In such embodiments, the compounds of the present invention or compositions containing the same, can be advantageously employed in combination with one or more additional pesticidal compounds. Such additional pesticidal compounds may be insecticides, nematocides, miticides, arthropodicides, or bactericides that are compatible with the compounds of the present invention in the medium selected for application and not
antagonistic to the activity of the present compounds.
Accordingly, in such embodiments, the pesticidal compound is employed as a supplemental toxicant for the same or for a different pesticidal use or as an
additive. The compounds in combination can generally be present in a ratio of from 1:100 to 100:1.
The exact amount of the active material to be applied is dependent not only on the specific active material being applied, but also on the particular action desired, the fungal species to be controlled and the stage of growth thereof as well as the part of the plant to be contacted with the toxic active ingredient. Thus, all of the active ingredients of the present invention and compositions containing the same may not be equally effective at similar concentrations or against the same fungal species.
The compounds in accordance with the invention may be applied in the form of any of the generally used formulation types, for example as solutions, dusts, wettable powders, flowable concentrates, or
emulsifiable concentrates.
The invention includes within its scope a method for the control or prevention of fungal attack, which method comprises applying to the locus of the fungus, or to a locus in which the infestation is to prevented, (for example applying to cereal grain plants), a fungicidal amount of one or more of the compounds.
A number of preferred embodiments of the invention are illustrated in the following Examples.
Example 1
Preparation of N-(1-(4-t butylphenyl)prop-2-yl)-N'N"- trimethylenequanidinium chloride
a) Preparation of 1-(4-t-butylphenyl)
-2-nitroprop-1-ene
12.4g of 4-t butylbenzaldehyde, 30 ml of
nitroethane and 2.9g of ammonium acetate were refluxed
together under nitrogen for 4 hours. The nitroethane was distilled off and the residue taken up in
ethylacetate. This was washed twice with water, dried, filtered and the solvent evaporated off. The residue was distilled at 90ºC (0.5 torr) Hg to afford a lemon yellow oil. Elemental analysis indicated the
following:- C = 71.3%; H = 7.85%; N = 6.5%;
(calculated, C = 71.2%; H = 7.80%; N = 6.4%).
b) Preparation of 1-(4-t butylphenyl)propan-2-amine
7.6g of the nitroolefin prepared in (a) above was dissolved in 150 ml dry diethylether and added dropwise to 10g of lithium aluminium hydride in 300 ml
diethylether under nitrogen with stirring. On
completion of addition the mixture was refluxed for 24 hours. 35 ml of triethanolamine was added over 2 hrs with cooling and then 9 ml water added dropwise. The mixture was stirred for 2 hrs and the resulting
suspension of sandy consistency filtered. The solids collected were washed with diethylether and the
washings combined with the organic solution. This was washed, dried with MgSθ4 filtered, the solvent
evaporated under reduced pressure and the residue distilled at 65ºC, (0.44 torr) to afford 5.4 g of an oil. NMR and IR spectra were consistent with the title compound
c) Preparation of 2-(1-(4-t butylphenyl)
propan-2-amino)pyrimidine
4.5g of 1-(4-t-butylphenyl)-propan-2-amine, 2.68g of 2-chloropyrimidine and 3.05g of ethyldiisopropylamine, all in 40 ml pentanol, were refluxed under nitrogen for 24 hours. The solvent was distilled off at reduced pressure and the residue taken up in dichloromethane and washed three times with water. The organic layer was dried with MgSO4, filtered and the solvent
removed under reduced pressure. The residue was
chromatographed on silica gel, EtOAc/hexane to yield 3.4g of a yellowish solid. Elemental analysis
indicated the following;
C = 75.5%; H = 8.5%; N = 14.2%
(calculated, C = 75.8%; H = 8.6%; N = 15.6%).
d) 1g of 2-(1-(4-t-butylphenyl)propan-2-amino) pyrimidine was dissolved in 25 cc absolute ethanol, and 150 mg of 10% palladium on charcoal and 1 ml of 2N hydrochloric acid were added. The mixture was agitated and hydrogenated at atmospheric pressure until hydrogen uptake ceased. The mixture was filtered and the solvent removed under reduced pressure to afford 1g of a gum. NMR and IR spectrocopy of the product were consistent with the expected structure for the title compound of Example 1.
Example 2
Preparation of N-(2-(4-t-butylphenyl))ethyl-N',N"- trimethylene guanidinium bromide
4-t butylphenethylamine was prepared in a manner analogous to that used in steps (a) and (b) in Example 1, except that nitromethane was used in place of nitroethane in step (a).
1.2g of 4-t-butylphenethylamine and 1.6g
S-ethyl-N,N'-trimethylenethiuronium bromide were dissolved in 9 ml ethanol and refluxed for 24 hours. The solvent was evaporated off and the residue
chromatographed on silica (CHCl3/EtOH/AcOH) to afford 1g of a gum. Elemental analysis indicated the
following C = 55.2%; H = 7.75%; N = 11.6% (calculated, C = 56.5%; H ; 7.70; N = 12.3). NMR and IR spectra were consistent with the expected structure.
Examples 3 and 4
N-(1-(4-t-butylphenyl)prop-2-yl)-N',N"-pent-2,4 diyl guanidinium acetate (Example 3) and chloride (Example 4) were prepared by methods analogous with
those used in Example 1, except that 2-chloro, 4,6 dimethyl pyrimidine was used in place of 2-chloro pyrimidine in step (c), and in Example 5, acetic acid was used in place of hydrochloric acid. NMR and IR spectra were consistent with the expected structure.
Example 5
Preparation of N-(1-(4-hexylphenyl)proo-2-yl)-N',
N"- trimethyleneguanidinium chloride
The preparation was carried out in a manner analogous to that used in Example 1, except that
4-hexylbenzaldehyde was used instead of 4-t-butyl benzaldehyde. NMR and IR spectra were consistent with the expected structure.
Example 6
Preparation of N-(1-(4-(2-phenyl)ethyl
prop-2-yl)-N',N"-trimethylenequanidinium chloride
The preparation was carried out in a manner analogous to that used in Example 1, except that
4-styrylbenzaldehyde was used instead of
4-t-butylbenzaldehyde. The double bond of the styryl group was reduced in step (d). NMR and IR spectra were consistent with the expected structure.
Example 7
Preparation of N-(1-(4-phenyl)prop-2-yl)-N',
N"-trimethyleneguanidinium chloride
The preparation was carried out in a manner analogous to that used in Example 1, except that
4-phenylbenzaldehyde was used instead of 4-t-butyl benzaldehyde. NMR and IR spectra were consistent with the expected structure.
Example 8
Preparation of N-(1-(3-phenoxy)prop-2-yl)-N',
N"-trimethyleneguanidinium chloride
The preparation was carried out in a manner analogous to that used in Example 1, except that
3-phenoxybenzaldehyde was used instead of 4-t-butyl benzaldehyde. Elemental analysis indicated the
following C = 65.2%; H = 6.95%; N = 11.7% (calculated, C - 65.9%; H - 7.00%; N = 12.1%). NMR and IR spectra were consistent with the expected structure.
Test Procedures
The compounds of Examples 1 to 8 were tested in accordance with the following in vitro and in vivo test methods.
In Vitro Screen Method
Test compounds are generally dissolved in acetone and made up with distilled water to give a solution with a final concentration of compound of 400 ppm and 10 per cent acetone. 2 ml aliquots of the latter solutions are pipetted into sterile petri dishes, and 18 ml of agar is then added to each dish using an automatic agar plate pourer to give a final
concentration of compound of 40 ppm.
Once the agar is set, discs of pathogens are cut from stock agar plates using a cork borer, and placed (pathogen face down) onto the test agar surface.
Pathogens used in the primary screen include:- 1. Alternaria brassicola
2. Fusarium oxysporum phaseolicola
3. Pyrenophora teres
4. Botrytis cinerea
5. Pyricularia oryzae
6. Pseudocercosporella herpotrichoides.
Three pathogens are placed on each plate. Two replicates of each plate are set up and kept in an incubator at 20ºC.
The pathogens on plate 1 are assessed after 5 days and those on plate 2 after 8 days. The diameters of the fungal colonies are measured after the incubation period and compared to the control measurements.
Allowing for the diameter of the original disc,
percentage inhibition values are then calculated.
In Vivo Screen Method
Compounds are dissolved in acetone or water (as required) and made up with distilled water to give a final concentration of compound of 400 ppm (and 10% acetone where acetone is used).
For each compound 3 replicate plants per pathogen (at the 1 leaf stage for cereals and at least the 2 leaf stage for vines) are sprayed to run off. The plants are allowed to dry at room temperature for 24 hours prior to inoculation.
untreated control plants and plants sprayed with 10% acetone water or water (as required) are included for each pathogen.
Method for Erysiphe qraminis Hordei
Barley cv. Golden Promise is used as the host plant. Seeds are sown 8 per 3" pot (plants
approximately 2 weeks old). Spores are blown onto the test plants from the stock plants, which are then incubated at 20ºC, relative humidity 70% for 7 days. After a week symptoms are recorded. % infection is scored from 3 replicate plants and expressed as a % of acetone/water control plants. % control is then recorded.
Method for Puccinia recondita
Wheat cv. Tonic. Seeds are sown 1 cm deep in 4 rows per plastic tray 60 cm x 30 cm. Seedlings are inoculated at 1-2 leaf stage. 0.05 g of uredospores are put into 100 ml distilled water with a melting agent. This solution is sprayed onto seedlings leaving a fine coverage on the leaves. The plants are then incubated with 100% relative humidity at 15-20ºC for 4 days.
% infection is scored from 3 replicate plants and
expressed as a % of acetone/water control plants. % control is then recorded.
The results are shown in Table 1 and 2
respectively.
Claims (20)
1. An agricultural fungicidal composition comprising a compound of the formula:
wherein R1 and R7 are each independantly hydrogen or C1-C3 alkyl,
R2 is hydrogen or C1-C6 alkyl,
R3 and R4 independently, and each R5 independently are hydrogen or C1-C4 alkyl,
R6 is a cyclohexyl group or a monocyclic or bicyclic aromatic group, substituted with from 1 to 5 groups of the formula R8,
wherein R8 is halogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a tri-C1-C4-alkylsilyl group, or a phenoxy, phenyl, phenyl-C1-C2-alkylene, or phenyl-C2-alkenylene group, each optionally substituted on the phenyl or phenoxy group with one or more of halogen atoms, C1-C6 alkyl or C1-C6 alkyl or C1-C6 alkoxy groups, trihalomethyl groups, phenyl groups or phenoxy groups,
p is 0, 1 or 2,
Y is a group of the formula -(CR9R9)n-, wherein
n is 2, 3, or 4,
each R9 independently is hydrogen or C1-C4 alkyl and X is a suitable counter-ion,
together with an agriculturally acceptable carrier or diluent.
2. A composition as claimed in Claim 1, wherein R1 and R7 are each independently hydrogen, methyl or ethyl.
3. A composition as claimed in Claim 2, wherein R1 and R7 are each hydrogen.
4. A composition as claimed in any one of the preceding Claims, wherein Y is a group of the formula
-(CR9R9)3-, wherein R9 is as defined in Claim 1.
5. A composition as claimed in Claim 2, wherein Y is a group of the formula
-(CH2)3-, or -CHMeCH2CHMe-.
6. A composition as claimed in any one of the preceding Claims, wherein R2 is hydrogen.
7. A composition as claimed in any one of the preceding Claims, wherein R3 is methyl.
8. A composition as claimed in any one of the preceding Claims, wherein R4 and R5 are each hydrogen.
9. A composition as claimed in any one of the
preceding Claims, wherein p is 1.
10. A composition as claimed in any one of the
preceding Claims, wherein R6 is substituted phenyl.
11. A composition as claimed in Claim 10, wherein R6 is 4-t-butylphenyl or 4-trimethylsilylphenyl.
12. A method of preparing a composition as claimed in any one of the preceding Claims, which method comprises combining the said compound of formula I-A, I-B, or I-C with an agriculturally acceptable carrier or diluent.
13. A compound of the formula I-A, I-B or I-C as defined in Claim 1, wherein p is 1 or 2 and n is 3 or 4.
14. A method of preparing a compound of formula I-A, I-B, or I-C as defined in Claim 1, which method comprises reacting a compound of the formula
R6(CR5R5) pCR3R4- NH II
With a salt of the formula
III
wherein R1 to R7, Y, and p and X are as defined in Claim 1, and L is a suitable leaving group.
15. A method as claimed in Claim 14, wherein L is an alkylthio group.
16. A method of preparing a compound of formula I-A, I-B, or I-C as defined in Claim 1, which method comprises reducing a compound of the formula.
V 17. A method as claimed in Claim 15, wherein the reduction is carried out using hydrogen and a metallic catalyst in the presence of an acid.
18. A method as claimed in Claim 16 or Claim 17 for the preparation of a compound of the formula I-A I-B or I-C as defined in Claim 1, wherein the said compound of formula V is prepared by reacting a compound of the formula
II with a compound of the formula
IU
wherein R2 to R6, and each R9 independently, is as defined in Claim 1, and L is a leaving group.
19. A method as claimed in Claim 18, wherein the leaving group is a halogen, and the reaction is carried out in the presence of a base.
20. A method for the control or prevention of fungal infestation, which method comprises applying to the locus of the fungus, or in which the infestation is to be
prevented, a composition as claimed in any one of Claims 1 to 11, or a compound as claimed in Claim 13.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8922750 | 1989-10-10 | ||
GB898922750A GB8922750D0 (en) | 1989-10-10 | 1989-10-10 | Fungicidal compounds,their production and use |
PCT/GB1990/001555 WO1991005473A1 (en) | 1989-10-10 | 1990-10-09 | Fungicidal compositions, fungicidal compounds, their production and use |
Publications (2)
Publication Number | Publication Date |
---|---|
AU6507590A true AU6507590A (en) | 1991-05-16 |
AU647416B2 AU647416B2 (en) | 1994-03-24 |
Family
ID=10664306
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU65075/90A Ceased AU647416B2 (en) | 1989-10-10 | 1990-10-09 | Guanidines as fungicides |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0593438A1 (en) |
JP (1) | JPH05504946A (en) |
AU (1) | AU647416B2 (en) |
BR (1) | BR9007740A (en) |
CA (1) | CA2066164A1 (en) |
GB (1) | GB8922750D0 (en) |
NZ (1) | NZ235608A (en) |
WO (1) | WO1991005473A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BRPI0610817A2 (en) | 2005-05-19 | 2010-07-27 | Bayer Cropscience Ag | heterocyclic derivatives and benzoylamino substituted heteroaryl insecticides |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2988478A (en) * | 1958-12-22 | 1961-06-13 | Pfizer & Co C | Agricultural compositions and use |
CH630507A5 (en) * | 1977-10-11 | 1982-06-30 | Ciba Geigy Ag | Pesticides |
NL7711390A (en) * | 1977-10-18 | 1979-04-20 | Philips Nv | NEW 2-ARYLIMINO-HEXAHYDOPYRIMIDINES AND IMI-DAZOLIDINES, SALTS AND COMPLEXES THEREOF, METHOD FOR PREPARING THE NEW COMPOUNDS, AND FUNGICIDE PREPARATIONS BASED ON THE NEW COMPOUNDS. |
NL7810350A (en) * | 1978-10-16 | 1980-04-18 | Duphar Int Res | PREPARATION WITH GROWTH REGULATORY EFFECT AND USE OF THIS PREPARATION IN AGRICULTURE AND GARDEN CONSTRUCTION. |
US4931455A (en) * | 1988-01-07 | 1990-06-05 | Ube Industries, Ltd. | Alkylaminopyrimidine derivative and insecticide, acaricide and fungicide containing the same as active ingredient |
-
1989
- 1989-10-10 GB GB898922750A patent/GB8922750D0/en active Pending
-
1990
- 1990-10-09 NZ NZ23560890A patent/NZ235608A/en unknown
- 1990-10-09 EP EP90915139A patent/EP0593438A1/en not_active Withdrawn
- 1990-10-09 AU AU65075/90A patent/AU647416B2/en not_active Ceased
- 1990-10-09 WO PCT/GB1990/001555 patent/WO1991005473A1/en not_active Application Discontinuation
- 1990-10-09 CA CA 2066164 patent/CA2066164A1/en not_active Abandoned
- 1990-10-09 BR BR909007740A patent/BR9007740A/en not_active Application Discontinuation
- 1990-10-09 JP JP51395990A patent/JPH05504946A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
BR9007740A (en) | 1992-09-15 |
JPH05504946A (en) | 1993-07-29 |
EP0593438A1 (en) | 1994-04-27 |
GB8922750D0 (en) | 1989-11-22 |
CA2066164A1 (en) | 1991-04-11 |
NZ235608A (en) | 1991-08-27 |
WO1991005473A1 (en) | 1991-05-02 |
AU647416B2 (en) | 1994-03-24 |
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