DE2118468A1 - Fungizide Mittel - Google Patents
Fungizide MittelInfo
- Publication number
- DE2118468A1 DE2118468A1 DE19712118468 DE2118468A DE2118468A1 DE 2118468 A1 DE2118468 A1 DE 2118468A1 DE 19712118468 DE19712118468 DE 19712118468 DE 2118468 A DE2118468 A DE 2118468A DE 2118468 A1 DE2118468 A1 DE 2118468A1
- Authority
- DE
- Germany
- Prior art keywords
- active ingredient
- dialkylamino
- phenylhydrazones
- fungi
- benzaldehyde
- 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.)
- Pending
Links
- 239000000417 fungicide Substances 0.000 title claims description 5
- 241000233866 Fungi Species 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000007857 hydrazones Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 48
- 239000000460 chlorine Substances 0.000 description 27
- 238000012360 testing method Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- -1 pyrrolidino, morpholino, piperazino, N-methylpiperazino Chemical group 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 10
- 206010061217 Infestation Diseases 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000035784 germination Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- 241000227653 Lycopersicon Species 0.000 description 5
- 241000233614 Phytophthora Species 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 238000005554 pickling Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000003934 aromatic aldehydes Chemical class 0.000 description 3
- 235000013532 brandy Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- IBMUHJIDXFMZPI-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O.ClC1=CC=CC=C1C=O IBMUHJIDXFMZPI-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 208000012868 Overgrowth Diseases 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000722093 Tilletia caries Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- OXCWIBVQIALMOU-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)hydrazine Chemical compound C1=CC(NN)=CC=C1N1CCOCC1 OXCWIBVQIALMOU-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WDLGOEMKPPESKD-UHFFFAOYSA-N 1-N-(benzylideneamino)-4-N,4-N-dimethylbenzene-1,4-diamine Chemical compound CN(C1=CC=C(C=C1)NN=CC1=CC=CC=C1)C WDLGOEMKPPESKD-UHFFFAOYSA-N 0.000 description 1
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- IERHSIBWKDAZJR-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC=1C=C(C=O)C=CC1.OC=1C=C(C=O)C=CC1 IERHSIBWKDAZJR-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- FKWGCVDXJDEHGC-UHFFFAOYSA-N 4-hydrazinyl-2-methoxy-N,N-dimethylaniline Chemical compound CN(C1=C(C=C(C=C1)NN)OC)C FKWGCVDXJDEHGC-UHFFFAOYSA-N 0.000 description 1
- URUDZLDUJCDPDC-UHFFFAOYSA-N 4-hydrazinyl-N,N-dimethylaniline dihydrochloride Chemical compound Cl.Cl.CN(C1=CC=C(C=C1)NN)C URUDZLDUJCDPDC-UHFFFAOYSA-N 0.000 description 1
- UGXJJUSLMZKOLF-UHFFFAOYSA-N 4-hydrazinyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(NN)C=C1 UGXJJUSLMZKOLF-UHFFFAOYSA-N 0.000 description 1
- QRVYABWJVXXOTN-UHFFFAOYSA-N 4-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(C=O)C=C1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- SWGPIDCNYAYXMJ-UHFFFAOYSA-N 5-chloro-2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C=O SWGPIDCNYAYXMJ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001530056 Athelia rolfsii Species 0.000 description 1
- QAUYIVRMGCPTCX-UHFFFAOYSA-N C1(=CC=C(C=C1)NN)N1CCCCC1 Chemical compound C1(=CC=C(C=C1)NN)N1CCCCC1 QAUYIVRMGCPTCX-UHFFFAOYSA-N 0.000 description 1
- RBOLTWLMCMAPAU-UHFFFAOYSA-N CN(C1=C(C=C(C=C1)NN)NC(=O)C)C Chemical compound CN(C1=C(C=C(C=C1)NN)NC(=O)C)C RBOLTWLMCMAPAU-UHFFFAOYSA-N 0.000 description 1
- LOMZFBXBEVIUKX-UHFFFAOYSA-N CN(C1=CC=C(C=C1)NN)CC Chemical compound CN(C1=CC=C(C=C1)NN)CC LOMZFBXBEVIUKX-UHFFFAOYSA-N 0.000 description 1
- JYYVJNJCZYXLQC-UHFFFAOYSA-N CN(C1=CC=C(C=C1)NN=CC1=C(C=CC=C1)S(=O)(=O)O)C Chemical compound CN(C1=CC=C(C=C1)NN=CC1=C(C=CC=C1)S(=O)(=O)O)C JYYVJNJCZYXLQC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- JXUWPJCPZDTBBJ-UHFFFAOYSA-N N1(CCCC1)C1=CC=C(C=C1)NN Chemical compound N1(CCCC1)C1=CC=C(C=C1)NN JXUWPJCPZDTBBJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
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- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- IAVREABSGIHHMO-UHFFFAOYSA-N meta-hydroxybenzaldehyde Natural products OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 1
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- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
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- 230000003641 microbiacidal effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XGMBIIKVAUZZRB-UHFFFAOYSA-N n,n-diethyl-4-hydrazinylaniline Chemical compound CCN(CC)C1=CC=C(NN)C=C1 XGMBIIKVAUZZRB-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
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- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
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- 239000001965 potato dextrose agar Substances 0.000 description 1
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- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 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
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712118468 DE2118468A1 (de) | 1971-04-16 | 1971-04-16 | Fungizide Mittel |
| BE782046A BE782046A (fr) | 1971-04-16 | 1972-04-13 | Nouvelle composition fongicide |
| NL7204973A NL7204973A (enrdf_load_stackoverflow) | 1971-04-16 | 1972-04-13 | |
| IL39211A IL39211A (en) | 1971-04-16 | 1972-04-13 | Fungicidal compositions containing 4-dialkylaminophenylhydrazones of phenyl and naphthyl aldehydes and certain such novel compounds |
| CH544872A CH531830A (de) | 1971-04-16 | 1972-04-13 | Verwendung von 4-Aminophenylhydrazonen zur Bekämpfung von Pilzen |
| ZA722522A ZA722522B (en) | 1971-04-16 | 1972-04-14 | Fungicidal agents |
| FR7213104A FR2133713B1 (enrdf_load_stackoverflow) | 1971-04-16 | 1972-04-14 | |
| DD162312A DD103550A5 (enrdf_load_stackoverflow) | 1971-04-16 | 1972-04-14 | |
| IT7264/72A IT961101B (it) | 1971-04-16 | 1972-04-14 | Mezzo fungicida |
| BR2247/72A BR7202247D0 (pt) | 1971-04-16 | 1972-04-14 | Composicoes fungicidas |
| GB1731172A GB1333027A (en) | 1971-04-16 | 1972-04-14 | Use of certain phenylhydrazones as fungicidal agents |
| AT328172A AT314901B (de) | 1971-04-16 | 1972-04-14 | Fungizide Mittel |
| HUBA2731A HU164564B (enrdf_load_stackoverflow) | 1971-04-16 | 1972-04-14 | |
| PL1972154765A PL83689B1 (enrdf_load_stackoverflow) | 1971-04-16 | 1972-04-15 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712118468 DE2118468A1 (de) | 1971-04-16 | 1971-04-16 | Fungizide Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2118468A1 true DE2118468A1 (de) | 1972-10-26 |
Family
ID=5804885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712118468 Pending DE2118468A1 (de) | 1971-04-16 | 1971-04-16 | Fungizide Mittel |
Country Status (14)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0331061A1 (de) * | 1988-03-03 | 1989-09-06 | BASF Aktiengesellschaft | Substituierte Hydrazone und diese enthaltende Fungizide |
| WO2006029850A1 (en) * | 2004-09-14 | 2006-03-23 | The Genetics Company, Inc. | Hydrazone derivatives and their use as beta secretase inhibitors |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11858879B2 (en) * | 2017-06-23 | 2024-01-02 | City Of Hope | PARG inhibitors and method of use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1204878B (de) * | 1963-02-21 | 1965-11-11 | Bayer Ag | Akarizide Mittel |
-
1971
- 1971-04-16 DE DE19712118468 patent/DE2118468A1/de active Pending
-
1972
- 1972-04-13 IL IL39211A patent/IL39211A/en unknown
- 1972-04-13 BE BE782046A patent/BE782046A/xx unknown
- 1972-04-13 NL NL7204973A patent/NL7204973A/xx unknown
- 1972-04-13 CH CH544872A patent/CH531830A/de not_active IP Right Cessation
- 1972-04-14 BR BR2247/72A patent/BR7202247D0/pt unknown
- 1972-04-14 FR FR7213104A patent/FR2133713B1/fr not_active Expired
- 1972-04-14 GB GB1731172A patent/GB1333027A/en not_active Expired
- 1972-04-14 AT AT328172A patent/AT314901B/de not_active IP Right Cessation
- 1972-04-14 DD DD162312A patent/DD103550A5/xx unknown
- 1972-04-14 IT IT7264/72A patent/IT961101B/it active
- 1972-04-14 HU HUBA2731A patent/HU164564B/hu unknown
- 1972-04-14 ZA ZA722522A patent/ZA722522B/xx unknown
- 1972-04-15 PL PL1972154765A patent/PL83689B1/pl unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0331061A1 (de) * | 1988-03-03 | 1989-09-06 | BASF Aktiengesellschaft | Substituierte Hydrazone und diese enthaltende Fungizide |
| WO2006029850A1 (en) * | 2004-09-14 | 2006-03-23 | The Genetics Company, Inc. | Hydrazone derivatives and their use as beta secretase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2133713B1 (enrdf_load_stackoverflow) | 1976-08-06 |
| BR7202247D0 (pt) | 1974-01-17 |
| IL39211A (en) | 1974-12-31 |
| PL83689B1 (enrdf_load_stackoverflow) | 1975-12-31 |
| NL7204973A (enrdf_load_stackoverflow) | 1972-10-18 |
| CH531830A (de) | 1972-12-31 |
| IL39211A0 (en) | 1972-06-28 |
| GB1333027A (en) | 1973-10-10 |
| BE782046A (fr) | 1972-10-13 |
| AT314901B (de) | 1974-04-25 |
| IT961101B (it) | 1973-12-10 |
| FR2133713A1 (enrdf_load_stackoverflow) | 1972-12-01 |
| HU164564B (enrdf_load_stackoverflow) | 1974-03-28 |
| ZA722522B (en) | 1973-01-31 |
| DD103550A5 (enrdf_load_stackoverflow) | 1974-02-05 |
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