EP1018876A1 - Use of hydroxylamine derivatives, and method and preparations for increasing the tolerance of field crops against weather stresses - Google Patents
Use of hydroxylamine derivatives, and method and preparations for increasing the tolerance of field crops against weather stressesInfo
- Publication number
- EP1018876A1 EP1018876A1 EP98917479A EP98917479A EP1018876A1 EP 1018876 A1 EP1018876 A1 EP 1018876A1 EP 98917479 A EP98917479 A EP 98917479A EP 98917479 A EP98917479 A EP 98917479A EP 1018876 A1 EP1018876 A1 EP 1018876A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- general formula
- tolerance
- plant
- compound
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000002443 hydroxylamines Chemical class 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 27
- 230000001965 increasing effect Effects 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title description 17
- 244000037666 field crops Species 0.000 title description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical group O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000008030 elimination Effects 0.000 claims abstract description 4
- 238000003379 elimination reaction Methods 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 84
- 239000013543 active substance Substances 0.000 claims description 42
- 239000000243 solution Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 19
- 238000005507 spraying Methods 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 230000035784 germination Effects 0.000 claims description 7
- -1 bromo, amino Chemical group 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000002791 soaking Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 description 100
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000003795 chemical substances by application Substances 0.000 description 42
- 238000002474 experimental method Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 229940093499 ethyl acetate Drugs 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 230000035882 stress Effects 0.000 description 16
- 229940125782 compound 2 Drugs 0.000 description 15
- 238000011282 treatment Methods 0.000 description 14
- IAJRBASJKPAYBJ-UHFFFAOYSA-N 3-nitro-n-(3-piperidin-1-ylpropoxy)benzenecarboximidoyl chloride;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=CC(C(Cl)=NOCCCN2CCCCC2)=C1 IAJRBASJKPAYBJ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 240000008042 Zea mays Species 0.000 description 13
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
- 235000009973 maize Nutrition 0.000 description 13
- 239000004372 Polyvinyl alcohol Substances 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 description 12
- 244000068988 Glycine max Species 0.000 description 11
- 235000010469 Glycine max Nutrition 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000011161 development Methods 0.000 description 10
- 230000018109 developmental process Effects 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- JLIDBLDQVAYHNE-YKALOCIXSA-N abscisic acid group Chemical group C\C(\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C)=C\C(O)=O JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 230000004083 survival effect Effects 0.000 description 8
- 229940125898 compound 5 Drugs 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000009331 sowing Methods 0.000 description 7
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 230000024346 drought recovery Effects 0.000 description 6
- 230000003054 hormonal effect Effects 0.000 description 6
- 230000008929 regeneration Effects 0.000 description 6
- 238000011069 regeneration method Methods 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 229940001593 sodium carbonate Drugs 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 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 4
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical class CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002253 anti-ischaemic effect Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
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- 239000008187 granular material Substances 0.000 description 3
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- 230000004060 metabolic process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 230000005068 transpiration Effects 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- KWSJFTJPSLIAEH-UHFFFAOYSA-N 3-(2-hydroxy-3-piperidin-1-ylpropoxy)-1,1-dimethyl-2-phenylguanidine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N=C(N(C)C)NOCC(O)CN1CCCCC1 KWSJFTJPSLIAEH-UHFFFAOYSA-N 0.000 description 2
- FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010059245 Angiopathy Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
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- 230000006179 O-acylation Effects 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
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- 229960000789 guanidine hydrochloride Drugs 0.000 description 2
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- 239000005556 hormone Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 150000002465 imidoyl halides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- MVLOQULXIYSERZ-UHFFFAOYSA-N n'-(2-hydroxy-3-piperidin-1-ylpropoxy)pyridine-3-carboximidamide Chemical compound C1CCCCN1CC(O)CONC(=N)C1=CC=CN=C1 MVLOQULXIYSERZ-UHFFFAOYSA-N 0.000 description 1
- LNPBUADXVNTUKA-UHFFFAOYSA-N n'-phenyl-n-(3-piperidin-1-ylpropoxy)benzenecarboximidamide Chemical compound C1CCCCN1CCCONC(C=1C=CC=CC=1)=NC1=CC=CC=C1 LNPBUADXVNTUKA-UHFFFAOYSA-N 0.000 description 1
- CHRDOERYBYSMEV-UHFFFAOYSA-N n'-phenyl-n-(3-piperidin-1-ylpropoxy)benzenecarboximidamide;hydrochloride Chemical compound Cl.C1CCCCN1CCCONC(C=1C=CC=CC=1)=NC1=CC=CC=C1 CHRDOERYBYSMEV-UHFFFAOYSA-N 0.000 description 1
- ATIGGIJEVHORCN-UHFFFAOYSA-N n-(2-hydroxy-3-piperidin-1-ylpropoxy)-2-nitrobenzenecarboximidoyl chloride;hydrochloride Chemical compound Cl.C1CCCCN1CC(O)CON=C(Cl)C1=CC=CC=C1[N+]([O-])=O ATIGGIJEVHORCN-UHFFFAOYSA-N 0.000 description 1
- HPNBPCVAJIMXAR-UHFFFAOYSA-N n-(2-hydroxy-3-piperidin-1-ylpropoxy)benzenecarboximidoyl chloride;hydrochloride Chemical compound Cl.C1CCCCN1CC(O)CON=C(Cl)C1=CC=CC=C1 HPNBPCVAJIMXAR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 230000037039 plant physiology Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229940084879 selective beta blocking agent Drugs 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- This invention relates to the use of hydroxylamine derivatives of general formula (I), wherein
- R represents phenyl, N-heteroaryl, S-heteroaryl or a naphthyl group which may be substituted with one or more halo, alkyl, alkoxy, haloal- kyl or nitro, an unsubstituted or substituted phenylamino or alky- lamino or lower alkoxy,
- X represents halo, preferably chloro or bromo, amino or an unsubstituted or substituted phenylamino group, or amino substituted with one or two lower alkyl or a hydroxy group provided that if R represents unsubstituted or substituted phenylamino, alkylamino or lower alkoxy, then X may not represent halo,
- Y represents hydrogen, hydroxy or acyloxy, preferably longer alkanoy- loxy, or if Y represents hydroxy, the molecule may contain a dioxazine ring closed at the carbon atom carrying the X group formed by formal XH elimination,
- R and R independently from each other, represent hydrogen or lower alkyl group provided that R 2 and R 3 may not represent hydrogen simultaneously,
- weather stresses such as cold, frost and drought cause significant losses for the agriculture.
- weather stresses may occur in any period of the growth or vegetation of the plant. Although they affect the plants in various ways and the plants react to them differently according to species and type, the effect is usually connected to the water metabolism of the plants.
- the protection of plants against weather stresses is made more difficult by the widely varied distribution of the time, strength and length of these stresses present at most agricultural regions.
- a temperature is considered cold if it is less than the minimum temperature necessary for normal physiological functioning of the individuals belonging to a given plant species or type, but greater than the freezing point of the water. Generally its effect may not be determined immediately by simple observation. The damage caused by the cold appears later, after warming up, such as the decrease in plant growth, the withering or fading (chlorosis), or in the most severe cases, death of the plant.
- frost i.e. the temperature below zero degree centigrade does not necessarily cause the plant to perish. After it is gone, the plant may be regenerated but the irreversible cell damages caused by the frost will strain its development, which will decrease its yield in the end.
- growth regulating materials which are compounds of hormonal activity, affect the cold, frost and drought tolerance of plants positively, and therefore they are applied for the treatment of cultivated plants.
- a typical example is abscisic acid, which is a growth regulating hormone. Abscisic acid itself is difficult to synthesise and hence it is not applied in agriculture.
- materials analogous to abscisic acid chemically and in their effect are used, which have identical or stronger effect than the abscisic acid itself , especially when combined with other compounds, which ensures a synergetic increase in the effect.
- 9608481 Al describes that plants are treated with epoxycyclohexane derivatives so as to make their development and yield more favourable and to increase their tolerance against cold and drought. Besides these compounds, brassidosteroids are also used as synergetic auxiliarys.
- the EP No. 327309 Al describes a compound that contains a poly-substituted cyclohexenyl-acetylene derivative as effective agent, and a diversely and multi-substituted phenyl-benzyl- urea derivative as synergetic auxiliary. With the help of this substance of hormonal activity, the tolerance of the plant against drought may be improved.
- secondary or tertiary ⁇ -hydroxyethyl-amines or respective quaternary ammonium salts preferably 2-hydroxy-ethyl-amines and trimethyl- ⁇ -hydroxy-ethyl- ammonium-chloride (choline-chloride) and, in certain cases, combinations of these may be applied to improve the tolerance of plants against cold and frost.
- the effective agent is applied to the plant by spraying. It may be concluded from the experimental section of the Patent that the effective agent is aimed at changing the phospholipid composition of the membrane of plant cells, and thus the fluidity, of the membrane. Hence the mentioned effective agents may be applied for the treatment of fully developed plants only.
- the substance is utilised, as described in the above mentioned paper, and this effect causes among others the improved tolerance of the sprouting plant against cold.
- the growth regulating substances of hormonal activity possess all of the disadvantages described above.
- R represents phenyl, N-heteroaryl, S-heteroaryl or a naphthyl group which may be substituted with one or more halo, alkyl, alkoxy, haloal- kyl or nitro, an unsubstituted or substituted phenylamino or alky- lamino or lower alkoxy,
- X represents halo, preferably chloro or bromo, amino or an unsubstituted or substituted phenylamino group, or amino substituted with one or two lower alkyl or a hydroxy group provided that if R represents unsubstituted or substituted phenylamino, alkylamino or lower alkoxy, then X may not represent halo,
- Y represents hydrogen, hydroxy or acyloxy, preferably longer alkanoy- loxy, or if Y represents hydroxy, the molecule may contain a dioxazine ring closed at the carbon atom carrying the X group formed by formal XH elimination,
- R 2 and R 3 independently from each other, represent hydrogen or lower alkyl group provided that R 2 and R 3 may not represent hydrogen simultaneously,
- R 2 and R 3 along with the adjacent nitrogen atom form a 5 to 7- membered saturated hetero ring, show the required effect and satisfy the mentioned requirements.
- this invention relates to the use of hydroxylamine derivatives of general formula (I), where R 1 , X, Y, R 2
- a lower alkyl group contains preferably 1-6 carbon atoms, most preferably 1-4 carbon atoms, and a lower alkoxy group contains 1-6, preferably 1-4 carbon atoms.
- R is a substituted phenyl or phenylamino group
- the alkyl groups attached to the phenyl ring as substituents are preferably lower 1-6 carbon atom alkyl groups.
- the alkoxy substituents of the phenyl ring preferably contain 1-6 carbon atoms.
- the haloalkyl substituents of the phenyl ring contain preferably alkyl, most preferably Ci-6 alkyl.
- haloalkyl substituent is the trifluoro- methyl group.
- R represents alkylamino, it preferably contains at most 12 carbon atoms.
- R represents N-heteroaryl, it is preferably pyridyl or pyrazinyl group, while if R represents an S-heteroaryl group, it is preferably tienyl.
- Y represents a long carbon chain alkanoyloxy, it preferably contains 12-20 carbon atoms.
- hydroxylamine derivatives of general formula (I) are known compounds.
- Those compounds of general formula (I) in which R represents phenyl or pyridyl or naphtyl which may be substituted with halo or alkoxy, X represents amino and Y represents hydroxy, are known from Hungarian Patent No. 177.578, which also describes the process of preparation of these compounds, as well as the different possibilities for synthesis.
- These compounds, as selective beta-blocking agents, may be applied in the therapy of angiopathy, primarily diabetic angiopathy.
- R represents phenylamino which is unsubstituted or substituted with alkyl, alkoxy, halo, haloalkyl or nitro, or an alkoxy or alkylamino group
- X represents hydroxy
- Y is hydrogen, hydroxy or alkanoyloxy
- tautomery may occur, i.e. they may appear in a tautomeric structure different from but corresponding to the formula (I).
- compounds of general formula (I) contain a hydroxy group as X, where the tautomeric version containing a -(CO)-NH- molecule part not appearing in the structural formula is more stable.
- New compounds are those hydroxylamine derivatives of general formula (I), in which X represents halo, Y is hydroxy, and R .. represents a group that is different from the ones described in the above mentioned Hungarian Patent No. 207.988 dealing with these kinds of compounds, for example phenyl substituted with alkyl, haloalkyl or nitro.
- These substances are prepared analogously to the cited description by diazotating the corresponding compound containing a NH2 group in the place of X.
- the necessary starting amino compounds are produced also by known method, by the coupling reaction of the corresponding amidoxime and a 3-amino-2-propanol derivative, for example according to the method described in the Hungarian Patent No. 177.578.
- N-substituted amidoximes of general formula (I), where R represents an aromatic group and X represents a substituted amino group are also novel compounds, and may be produced by the coupling reaction of a suitable imidoyl-halide of general formula (1), wherein Hal represents a halo and R is as above, while R' is the substituent of the amino group of X, and a l-amino-3-aminooxy- propane derivative of general formula (2), where R 2 , R and Y are as above.
- the reactions should be performed in a neutral solvent, for example in chlorinated hydrocarbon, at room temperature and after extraction separation, the product is isolated as a salt with a suitable organic or inorganic acid.
- novel compounds of general formula (I) are N-hydroxy- guanidine derivatives in which both R and X are substituted nitrogen atoms. These derivatives are produced by the acylation of a suitable aminooxy compound of general formula (2), if the acylating agent is haloformamidine of general formula (3), where Hal represents halogen, R is as above, and R' and R" are substituents of the amino group appearing as X in the product.
- the reaction is performed in a two phase system, in the mixture of some organic solvent not mixable with, water and a aqueous base, preferably aqueous sodium-carbonate solution.
- the product is isolated in this case also by extraction separation and, if possible, by salt- formation.
- Any of those new compounds of general formula (I), in which Y represents acyloxy, may be produced by O-acylation of the corresponding compound containing hydroxy as Y.
- the starting compounds are either known from the above mentioned literature or may be produced according to the method described.
- acylating agent acid halides, active esters or other usual reagents applicable for O-acylation may be used.
- the reactions can be performed in a neutral solvent, usually at room temperature and if necessary in the presence of a suitable acid-binding agent, such as an organic or inorganic base, for example triethylamine or solid sodium- carbonate.
- the acid chlorides are preferable, where the compound itself may behave as acid-binding agent, and hence usually the product may be easily isolated in the form of hydrochloride by simple ethereal crystallisation after evaporation.
- the product may be easily isolated in the form of hydrochloride by simple ethereal crystallisation after evaporation.
- Schotten-Baumann acylation may also be applied.
- the products are generally isolated in the form of their salt with a organic or an inorganic acid.
- Compound 15 Compounds of general formula (I) are favourable with respect to application in the cultivation of plants because they are suitable for treating both the fully developed plant and the seed or the seedling. These compounds may be applied to the plants using any of the usual procedures widely used in plant-protection. Based on the above, the invention relates to a procedure to increase the tolerance of cultivated plants against weather stresses. According to the invention, the protected plant or its seed is treated with a hydroxylamine derivative of general formula (I), where R , X, Y,
- R 2 and R 3 are as above.
- an aqueous solution of the com- pound of general formula (I) is used for the treatment, but alternatively a preparation containing the usual carriers and the hydroxylamine derivative of general formula (I) as effective agent may be applied.
- the dose and the concentration of the effective agent of general formula (I) is dependent on the protected plant species or type and on the method of the application.
- the procedure according to the invention is aimed at improving the tolerance of the plant against cold and frost, preferably the seed of the plant should be treated with a hydroxylamine derivative of general formula (I), where
- R 1 , X, Y, R 2 and R 3 are as above.
- the seed of the plant must be covered with the proper product containing the active agent and suitable for coating, preferably pearled, in certain cases dressed, or the aqueous solution of the effective agent may simply be used.
- the preferable method is to soak the seed of the plant in an aqueous solution of a compound of general formula (I). For this purpose a 1-200 mg/1 concentration of the compound of general formula (I) in aqueous solution is prepared.
- the procedure according to the invention may be performed by coating the seed of the plant with a solution containing a hydroxylamine derivative of general formula (I).
- the compounds of general formula (I) may be combined with dressing agents in certain cases.
- pearling agents are applied, which contain compounds of general formula (I) in a concen- tration of 0.1- 10 g/1 along with the usual pearling and auxiliary materials.
- the pearling agents may contain other effective agents beside the mentioned effective agent as well, such as fungicides or additives promoting germination, for example microelements.
- the pearling agent is applied in a small volume. For example, when treating bean, soybean or maize seeds, only 1 ml or less amount of pearling agent is used for
- this invention relates to a procedure for improving the tolerance of cultivated plants against cold, where the plant is sprayed before or at the time when the cold season sets in with a spray preparation containing a hydroxylamine derivative of general formula (I) as effective agent.
- the spraying is performed with a 1-500 mg/litre concentration aqueous solution of the effective agent, which may occasionally contain spraying auxiliary materials, such as surface active material (detergent).
- auxiliary materials such as surface active material (detergent).
- compounds of general formula (I) may be combined and sprayed to the plant to be protected with other effective agents such as fungicides.
- the spraying is to be performed at the beginning of the period hazardous in terms of cold temperature. If more than one period is to be taken into consideration, then the plants must be sprayed at the beginning of each such period.
- the plant to improve the tolerance of cultivated plants the plant must be sprayed before or at the time when the dry season sets in with a spray preparation containing a hydroxylamine derivative of general formula (I) as effective agent.
- the spraying is performed using a 1-500 mg/1 aqueous solution of the active agent.
- the plants to be protected are sprayed before or at the beginning of the period when there is a risk of drought. In every case, the characteristics of the given plant species or type determine the applicable quantity of the active agent. If more than one drought period is to be taken into consideration, then the spraying must be repeated at the beginning of each such period.
- a simple aqueous solution of the hydroxylamine derivatives of general formula (I), but preferably such preparations are used which contain proper auxiliary materials beside the active agent, for improving the spraying, distribution and the absorption of the active agent.
- composition of the invention for improving the tolerance of cultivated plants against weather stresses contains 0.001-95 m/m% hydroxylamine derivative of general formula (I), in which R 1 , X, Y, R 2 and R 3 are as above, beside the solid or liquid carriers and possible auxiliary materials suitable for agricultural application.
- the composition preferably contains water as liquid vehicle agent.
- the aqueous solution of the active agent is a concentrate, which should be diluted before application in order to prepare the proper concentration mentioned above.
- the aqueous solutions contain surfactants, those solutions for treating the seed contain dressing and pearling auxiliary materials, such as film forming materials.
- the sprays contain an adhesion improving agent, a substance to improve spreading, light protecting agent, if required, a stabilising agent and other additives beside the detergents.
- ULV concentrates, emulsif ⁇ able concentrates, hydrophyl powders, soluble granulates or microgranulates dilutable with water may be applied.
- These products contain anionic or non-anionic detergents in order to help the dilution with water.
- the solid products may contain kaolin, diatomite or dolomite as vehicle, but may also contain any other solid vehicle agent widely applied in such products.
- perlite is used as vehicle agent for the production of microgranulate.
- compositions of the invention may be combined or simultaneously applied with other pesticides, if the active agent of the latter is compatible with the active agent of the composition of the invention. In these cases, the spraying of the composition of the invention does not require a separate process, it can be performed along with the usual pesticide treatment of the cultivated plants.
- N-[2-hydroxy-3-(l-piperidinyl)propoxy]-2'-nitro- benzenecarboximidoyl chloride monohydrochloride (Compound 5) 6.0 g (16.7 mmol) of N-[2-hydroxy-3-(l-piperidinyl) propoxy]-2'- nitro-benzene-carboximidamide monohydrochloride is dissolved in 21 ml of water, then 48 ml of concentrated hydrochloric acid is added. The solution is cooled to -5 °C, then a cold solution of 2.1 g (33.3 mmol) of sodium nitrite in 9 ml of water is added dropwise. Throughout the reaction the internal temperature is maintained at 0 C. When the addition is completed, the mixture is stirred for a further four hours and cooled overnight. The product is filtered off, washed with cold water and dried.
- the resulting base is dissolved in (5.33 g) 50 ml of ethyl-acetate and then 3.35 ml of 3.67 N hydrochloric acid /ethyl-acetate is added.
- the isolated crystals are filtered off, washed with ethyl-acetate and dried.
- N,N-dimethyl-N'-phenyl-N"-[2-hydroxy-3-(l-piperidinyl)propoxy]- guanidine hydrochloride (Compound 13) 1, 150 mg (6.58 mmol) l-aminooxy-2-hydroxy-3-(l-pi ⁇ eridinyl)- propane] is dissolved in 20 ml of ether and to this solution 20 ml of 1 M sodium carbonate solution is added, then 1,206 mg (6.58 mmol) of N,N- dimethyl-N'-phenyl-chloroformamidine dissolved in 10 ml of ether is added.
- Results marked with * are significant compared to the control, if
- Results marked with * are significant compared to the control, if P ⁇ 0.05.
- Results marked with * are significant compared to the control, if. It was further observed that Compound 8 decreased the number of ungerminating seeds by 50% (control: 33%, treated: 17%, significant at P ⁇ 0.05).
- Control: 33%, treated: 17%, significant at P ⁇ 0.05 did not influence the germination of the seeds and the development of the plants kept at 25°C. Under the circumstances of the CSVT test, they increased the length of the sprouts and the roots along with the proportion of the high vigour seedlings. The ratio of the ungerminating seeds decreased by 30% on average due to the treatment with the active agents. The results are demonstrated in Table 5.
- Results marked with * are significant compared to the control, if P ⁇ 0.05.
- the CSVT procedure is developed to predict the expected minimal ratio of sprouting seeds under environmental stresses.
- the ratio of those seeds that safely sprout and properly germinate in cold spring weather is 90% for seeds which proved to be of high vigour in the CSVT test, while the ratio of those seeds which safely sprout and properly germinate in cold spring weather is only 60% for seeds that proved to be of low vigour in the test.
- an active agent improves the vigour of the seedlings, it in the end improves the sprouting ratio under open field conditions in the case of ground temperature colder than optimal.
- the above experiments prove that the compounds of general formula (I) are able to improve the vigour of the seedlings and hence improve the chance of sprouting, if unexpectable weather stresses occur after the sowing.
- Soybean seeds are treated with a pearling agent, which contains 1 mg/ml of N-[3-(l-piperidinyl)propoxy]-3-nitro-benzimidoyl-chloride monohydrochloride (Compound 4) in a 5% aqueous polyvinylalcohol solution.
- a pearling agent which contains 1 mg/ml of N-[3-(l-piperidinyl)propoxy]-3-nitro-benzimidoyl-chloride monohydrochloride (Compound 4) in a 5% aqueous polyvinylalcohol solution.
- Results marked with * are significant compared to the control, if P ⁇ 0.05.
- PVA slightly increased the ratio of high vigour plants.
- the PVA solution containing Compound 4 proved to be such a pearling agent which was able to increase the ratio of high vigour plants significantly under the experimental conditions, increasing the length of both the sprouts and the roots.
- the plants were hardened before the application of the active agent; by withholding the water for a few days, until the first signs of withering appeared. Then the plants were watered and the active agent was either dissolved in the water, or sprayed to the plants directly. Afterwards, the plants were subjected to different periods of drought according to the given experiment, watered again, and after a week-long regeneration period, the survival ratio was determined. a) Seaway bean cultivar was hardened for 5 days by withholding the water. Afterwards the plantlets were watered for two days nor- mally.
- Results marked with * are significant compared to the control, if P ⁇ 0.05.
- Results marked with * are significant compared to the control, if P ⁇ 0.05.
- Soybeans of soybean cv. B ⁇ lyi 44 were hardened for 6 days by withholding the water. This was followed by two days of watering, and the active agent was applied in the water. The concentration of the solution of the active agent was 50 mg/ litre. After a 4-day-long cease of watering and a one week regeneration period, the number of surviving plants was recorded. The results are listed in Table 10. Table 10.
- Results marked with * are significant compared to the control, if P ⁇ 0.05.
- Seedlings of bean cv. Seaway were cultivated under normal conditions for the first two weeks, then they were treated with 10 mg/ litre and 100 mg/ litre concentration solutions of the examined active agents 2 and 1 days before the initiation of the frost tolerance experiments. In the experiment, the plants were kept at -2°C for 8 hours, then grew under normal conditions for 1 week, and the survival ratio was determined. 4 trays were used for each experiment and 6 seeds were planted in each tray. The compounds in Table 1 1. significantly increased the survival ratio. Table 11.
- Results marked with * are significant ⁇ ;ompared to the control, if
- the experiment was performed using the Mo 17 maize inbred line.
- the seeds were coated with a 2% solution of the examined compound dissolved in 2 ml polyvinylalcohol before germination, where the above quantity of solution is applied for 100 seeds.
- the seeds were germinated for 3 days wrapped in wet filter paper, they were sown and then cultivated in gradient chamber for 6 weeks. In the gradient chamber, the temperature was maintained on a scale between 1 and
- the experiment was performed using soybean cv. B ⁇ lyi 44. Before sowing, the seeds were treated with Rhyzobium Japonicum nitrogen- binding bacterium, which forms a root nodule providing 50-70% of the nitrogen demand of the plant.
- the examined compounds were applied by pearling the seeds; 1 ml of pearling agent containing 1 mg of active agent in a 5% aqueous PVA solution was used for 100 seeds.
- the experiments were perfomed on the Mo 17 and AMO 406 lines. Before sowing, the seeds were dressed with fungicides, insecticides and rodent-control agents, and, at the same time, the tested compounds were applied in the form of a 2.5 mg/ml concentration solution in a 2% PVA solution; 2 ml of solution was used for 100 seeds.
- the foliar spray is prepared with the following composition (proportions by weight) :
- Foliar spray is prepared with the following composition (proportions by weight): Compound 4 20 alkyl-aryl-sulphonate 5 water 75
- Pearling agent is prepared with the following composition (proportions by weight) :
- the pearling agent must be applied as active agent in a quantity of 0.01-0.02 m/m% with respect to the weight of the seed.
- Granulate is prepared with the following composition
- the mixture of the components must be ground in a hammer mill until it reaches the particle size of 5 micron.
- Powder preparation is prepared with the following composition (proportions by weight) : Compound 6 50 poly-vinyl-pyrrolidon 10 silicon-dioxide 25 china-clay (kaolin) 15 Example 20 Powder preparation
- Powder preparation is prepared with the following composition
- Compound 1 50 calcium-ligninesulphonate 5 isopropyl-naphtalene-sulphonate 1 silicon-dioxide 4 filler (kaolin) 40
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- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU9700792 | 1997-04-22 | ||
HU9700792A HU9700792D0 (en) | 1997-04-22 | 1997-04-22 | Hydroxil-amine derivatives, preparation and use thereof, composition containing these compounds as active ingredients and same use for plants protection against extremity weather conditions |
HU9702365A HUP9702365A3 (en) | 1997-04-22 | 1997-12-05 | Application of hydroxilamin-derivatives, as well as process and composition for increase of weather extreme resistent by cultivated plants |
HU9702365 | 1997-12-05 | ||
PCT/HU1998/000039 WO1998047362A1 (en) | 1997-04-22 | 1998-04-21 | Use of hydroxylamine derivatives, and method and preparations for increasing the tolerance of field crops against weather stresses |
Publications (1)
Publication Number | Publication Date |
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EP1018876A1 true EP1018876A1 (en) | 2000-07-19 |
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EP98917479A Withdrawn EP1018876A1 (en) | 1997-04-22 | 1998-04-21 | Use of hydroxylamine derivatives, and method and preparations for increasing the tolerance of field crops against weather stresses |
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EP (1) | EP1018876A1 (id) |
JP (1) | JP2002514216A (id) |
AR (1) | AR012482A1 (id) |
AU (1) | AU748367B2 (id) |
BR (1) | BR9808976A (id) |
CA (1) | CA2288075A1 (id) |
CO (1) | CO5040008A1 (id) |
HR (1) | HRP980217A2 (id) |
HU (1) | HUP9702365A3 (id) |
ID (1) | ID20187A (id) |
IL (1) | IL132509A0 (id) |
NZ (1) | NZ500579A (id) |
WO (1) | WO1998047362A1 (id) |
Cited By (1)
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WO2013081457A1 (en) | 2011-11-28 | 2013-06-06 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Sealed thin-film device as well as method of repairing, system for repairing and computer program product |
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KR20040089102A (ko) | 2002-01-11 | 2004-10-20 | 비오렉스 쿠타토 에쉬 훼레스테 에르테 | 카르복사미딘 유도체 및 혈관 질환의 치료에서의 이들 용도 |
WO2003076375A1 (en) * | 2002-03-14 | 2003-09-18 | National Institute Of Agrobiological Sciences | Novel diterpenoids imparting stress resistance to plants |
CA2691333A1 (en) * | 2007-06-29 | 2009-01-08 | Harald Koehle | Strobilurins for increasing the resistance of plants to abiotic stress |
CA3237171A1 (en) * | 2021-09-28 | 2023-04-06 | Zevra Denmark A/S | Dioxazines and their use in treatment of gba-related diseases |
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- 1997-12-05 HU HU9702365A patent/HUP9702365A3/hu unknown
-
1998
- 1998-04-21 EP EP98917479A patent/EP1018876A1/en not_active Withdrawn
- 1998-04-21 BR BR9808976-5A patent/BR9808976A/pt not_active IP Right Cessation
- 1998-04-21 AU AU70703/98A patent/AU748367B2/en not_active Ceased
- 1998-04-21 IL IL13250998A patent/IL132509A0/xx unknown
- 1998-04-21 CA CA002288075A patent/CA2288075A1/en not_active Abandoned
- 1998-04-21 WO PCT/HU1998/000039 patent/WO1998047362A1/en not_active Application Discontinuation
- 1998-04-21 AR ARP980101827A patent/AR012482A1/es not_active Application Discontinuation
- 1998-04-21 JP JP54531498A patent/JP2002514216A/ja active Pending
- 1998-04-21 NZ NZ500579A patent/NZ500579A/en unknown
- 1998-04-22 ID IDP980602A patent/ID20187A/id unknown
- 1998-04-22 CO CO98022197A patent/CO5040008A1/es unknown
- 1998-04-22 HR HRP9702365A patent/HRP980217A2/hr not_active Application Discontinuation
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WO2013081457A1 (en) | 2011-11-28 | 2013-06-06 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Sealed thin-film device as well as method of repairing, system for repairing and computer program product |
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HU9702365D0 (en) | 1998-03-02 |
AR012482A1 (es) | 2000-10-18 |
JP2002514216A (ja) | 2002-05-14 |
HUP9702365A3 (en) | 1999-09-28 |
CA2288075A1 (en) | 1998-10-29 |
AU748367B2 (en) | 2002-06-06 |
HUP9702365A2 (hu) | 1999-01-28 |
ID20187A (id) | 1998-10-22 |
IL132509A0 (en) | 2001-03-19 |
NZ500579A (en) | 2001-10-26 |
AU7070398A (en) | 1998-11-13 |
BR9808976A (pt) | 2000-08-01 |
HRP980217A2 (en) | 1998-12-31 |
CO5040008A1 (es) | 2001-05-29 |
WO1998047362A1 (en) | 1998-10-29 |
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