GB2086228A - Preparations for Defoliating and/or Regulating the Growth of Plants and Their Use - Google Patents
Preparations for Defoliating and/or Regulating the Growth of Plants and Their Use Download PDFInfo
- Publication number
- GB2086228A GB2086228A GB8132217A GB8132217A GB2086228A GB 2086228 A GB2086228 A GB 2086228A GB 8132217 A GB8132217 A GB 8132217A GB 8132217 A GB8132217 A GB 8132217A GB 2086228 A GB2086228 A GB 2086228A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiadiazol
- thiadiazolin
- urea
- ide
- mixture
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 62
- 230000001105 regulatory effect Effects 0.000 title claims abstract description 13
- 230000008635 plant growth Effects 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000000126 substance Substances 0.000 claims abstract description 42
- HQYZTGGAEAFKIO-UHFFFAOYSA-N thiadiazol-5-ylurea Chemical class NC(=O)NC1=CN=NS1 HQYZTGGAEAFKIO-UHFFFAOYSA-N 0.000 claims abstract description 31
- MMASRHDDOSEHRC-UHFFFAOYSA-N 2,5-dihydrothiadiazole Chemical class C1SNN=C1 MMASRHDDOSEHRC-UHFFFAOYSA-N 0.000 claims abstract description 28
- 240000002024 Gossypium herbaceum Species 0.000 claims abstract description 17
- 235000004341 Gossypium herbaceum Nutrition 0.000 claims abstract description 17
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 9
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims abstract description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 8
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 claims abstract description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract 7
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract 7
- 239000010452 phosphate Substances 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims description 80
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 40
- 241000196324 Embryophyta Species 0.000 claims description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 22
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 22
- -1 trifluoromethylphenyl group Chemical group 0.000 claims description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- 239000004202 carbamide Substances 0.000 claims description 18
- OVAUYSRLAYJFPH-UHFFFAOYSA-N O=C(NC1=CC=CC=C1)N=C1SNN=C1 Chemical compound O=C(NC1=CC=CC=C1)N=C1SNN=C1 OVAUYSRLAYJFPH-UHFFFAOYSA-N 0.000 claims description 17
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 12
- 239000013543 active substance Substances 0.000 claims description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 159000000007 calcium salts Chemical class 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 8
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910000404 tripotassium phosphate Inorganic materials 0.000 claims description 8
- 235000019798 tripotassium phosphate Nutrition 0.000 claims description 8
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 7
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 7
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 claims description 7
- 239000001099 ammonium carbonate Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000012010 growth Effects 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Chemical group 0.000 claims description 6
- VJXKPMICAFCWKC-UHFFFAOYSA-N 1-pyridin-2-yl-3-(thiadiazol-5-yl)urea Chemical compound C=1C=CC=NC=1NC(=O)NC1=CN=NS1 VJXKPMICAFCWKC-UHFFFAOYSA-N 0.000 claims description 5
- 159000000003 magnesium salts Chemical class 0.000 claims description 5
- 150000002696 manganese Chemical class 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000003223 protective agent Substances 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 claims description 4
- 239000001488 sodium phosphate Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 235000019818 tetrasodium diphosphate Nutrition 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical group [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 4
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims description 4
- 235000019801 trisodium phosphate Nutrition 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 235000011180 diphosphates Nutrition 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical group OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 2
- 239000000470 constituent Substances 0.000 abstract description 6
- 230000002195 synergetic effect Effects 0.000 abstract description 4
- 230000035613 defoliation Effects 0.000 description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 229910009112 xH2O Inorganic materials 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 210000002741 palatine tonsil Anatomy 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- ZAABECHFTWWWOU-UHFFFAOYSA-N CN(C(N=C1SNN=C1)=O)C1=CC=CC=C1 Chemical compound CN(C(N=C1SNN=C1)=O)C1=CC=CC=C1 ZAABECHFTWWWOU-UHFFFAOYSA-N 0.000 description 2
- 244000284380 Hibiscus rosa sinensis Species 0.000 description 2
- SIGOEOKJLYGCFC-UHFFFAOYSA-N O=C(NC1=NC=CC=C1)N=C1SNN=C1 Chemical compound O=C(NC1=NC=CC=C1)N=C1SNN=C1 SIGOEOKJLYGCFC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- AWLHKUPWFTWKCQ-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(thiadiazol-5-yl)urea Chemical compound ClC1=CC=CC(NC(=O)NC=2SN=NC=2)=C1 AWLHKUPWFTWKCQ-UHFFFAOYSA-N 0.000 description 1
- ZJWYOQHBYMIWKB-UHFFFAOYSA-N 1-(4-methylpyridin-2-yl)-3-(thiadiazol-5-yl)urea Chemical compound CC1=CC=NC(NC(=O)NC=2SN=NC=2)=C1 ZJWYOQHBYMIWKB-UHFFFAOYSA-N 0.000 description 1
- QEWUOBBMUVABBY-UHFFFAOYSA-N 1-(6-methylpyridin-2-yl)-3-(thiadiazol-5-yl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2SN=NC=2)=N1 QEWUOBBMUVABBY-UHFFFAOYSA-N 0.000 description 1
- MJVIZWIQHKRBPI-UHFFFAOYSA-N 1-(aziridin-1-yl)but-3-en-2-ol Chemical compound C=CC(O)CN1CC1 MJVIZWIQHKRBPI-UHFFFAOYSA-N 0.000 description 1
- GIQXLBILFSQJRG-UHFFFAOYSA-N 1-methyl-1-phenyl-3-(thiadiazol-5-yl)urea Chemical compound C=1C=CC=CC=1N(C)C(=O)NC1=CN=NS1 GIQXLBILFSQJRG-UHFFFAOYSA-N 0.000 description 1
- VZJJFYKWJUQLLH-UHFFFAOYSA-N 1-pyridin-4-yl-3-(thiadiazol-5-yl)urea Chemical compound C=1C=NC=CC=1NC(=O)NC1=CN=NS1 VZJJFYKWJUQLLH-UHFFFAOYSA-N 0.000 description 1
- HOUDZYFLQFMNQQ-UHFFFAOYSA-N 2-[2-[2-(2-nonoxyethoxy)ethoxy]ethoxy]ethoxybenzene Chemical compound CCCCCCCCCOCCOCCOCCOCCOC1=CC=CC=C1 HOUDZYFLQFMNQQ-UHFFFAOYSA-N 0.000 description 1
- JACPTQMMZGZAOL-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)CCS(O)(=O)=O JACPTQMMZGZAOL-KHPPLWFESA-N 0.000 description 1
- QIUPEXYJAZIUFR-UHFFFAOYSA-N C1(=CC=CC=C1)NC(=S)NC1=CN=NS1.CNC(=O)N(C1=CN=NS1)C.CN(C(=O)N(C1=CN=NS1)C)C Chemical compound C1(=CC=CC=C1)NC(=S)NC1=CN=NS1.CNC(=O)N(C1=CN=NS1)C.CN(C(=O)N(C1=CN=NS1)C)C QIUPEXYJAZIUFR-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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- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 1
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- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
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- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
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- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- IPSBXHDFMRENNC-UHFFFAOYSA-M sodium 1-pyridin-2-yl-3-(1-thia-3-aza-2-azanidacyclopent-3-en-5-ylidene)urea Chemical compound [Na+].N1=C(C=CC=C1)NC(=O)N=C1C=N[N-]S1 IPSBXHDFMRENNC-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Abstract
A synergistic mixture of (i) a defoliating and/or growth-regulating compound selected from 1,2,3- thiadiazol-5-yl-urea derivatives and 1,2,3-thiadiazolin-2-ide derivatives with (ii) a basically reactive substance is used for defoliating and/or regulating the growth of plants, preferably cotton plants. Preparations suitable for such use comprise the aforesaid constituents, the ratio by weight of the defoliating and/or growth-regulating compound to the basically reactive substance preferably being 1:0.5 to 1:1000. The defoliating and/or growth- regulating compound is, for example, 1-phenyl-3-(1,2,3-thiadiazol-5-yl)- urea and the basically reactive substance is, for example, an alkali hydroxide, amine, carbonate, phosphate or alkali salt of a monocarboxylic acid.
Description
SPECIFICATION
Preparations for Defoliating and/or Regulating the Growth of Plants and their Use
The present invention is concerned with preparations for defoliating and/or regulating the growth of plants, especially for the defoliation of plants, preferably cotton plants, comprising a compound selected from 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives with a basically reactive substance, and with the use of such preparations.
The term "plants" is understood herein to include trees and shrubs.
1 ,2,3-Thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives have already become known as agents for the defoliation of plants (German Offenlegungsschrift No. 2506690; German Offenlegungsschrift No. 2619861; German Offenlegungsschrift No. 2719810). These active substances are not, however, sufficiently effective in all cases.
Mixtures of 1 ,2,3-thiadiazol-5-yl-urea derivatives with other defoliating agents are also already known in which the substances, which, per se, already have a more or less strong defoliating action, are mutually potentiating in their action (German Offenlegungsschrift No. 2646712). The synergistic action of these mixtures is therefore dependent on two compounds that are already active.
The aim upon which the present invention is based has therefore been to provide an agent especially for the defoliation of plants, in which the action of the 1 ,2,3-thiadiazol-5-yl-urea derivatives or 1 ,2,3-thiadiazolin-2-ide derivatives already known to be active is increased by the addition of substances that are, per se, inactive as regards a defoliating and/or growth-regulating action.
This aim is achieved by the present invention.
The present invention accordingly provides a preparation for defoliating and/or regulating the growth of plants, which comprises a defoliating and/or growth-regulating compound selected from 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives, in admixture or conjunction with a basically reactive substance.
The present invention also provides a method of defoliating and/or regulating the growth of a living plant, wherein the living plant is treated with a mixture comprising (i) a defoliating and/or growthregulating compound selected from 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives and (ii) a basically reactive substance.
The present invention further provides a method of defoliating and/or regulating the growth of plants in a crop area, wherein the crop area is treated with a mixture comprising (i) a defoliating and/or growth-regulating compound selected from 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1,2,3thiadiazolin-2-ide derivatives and (ii) a basically reactive substance.
The preparations of the present invention may be in the form of concentrates which on dilution provide mixtures suitable for the methods of the present invention.
There is also included within the scope of the present invention a pack which comprises a preparation of the present invention, together with instructions for its use for defoliating and/or regulating the growth of living plants.
According to the present invention there come into consideration as the compounds having a defoliating and/or growth-regulating action:
A) 1 ,2,3-thiadiazol-5-yl-urea derivatives of the general formula I
in which R1 represents a hydrogen atom or a C1-C5-alkyl group,
R2 represents a C1-C5-alkyl group, a C5-08-cycloalkyl group, a phenyl, halogenated phenyl, 01-C4-alkylphenyl, C1-c4-alkoxyphenyl, nitrophenyl or trifluoromethyiphenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyrimidyl group substituted by one or more substituents (which may be the same or different) selected from C1-c4-alkyl groups, C,C4-aíkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or
R1 and R2 together with the adjacent nitrogen atom represent a morpholino, piperidino or pyrrolidino group, R3 represents a hydrogen atom or a C1-o5-alkyl group, and
X represents an oxygen or sulphur atom; and B) ,2,3-thiadiazolin-2-ide derivatives of the general formula II
:n wnicn R, represents a hydrogen atom or a C1-C5-alkyl group,
R2 represents a hydrogen atom, a C1-C5-alkyl group, a C5-c8-cycloalkyl group, a phenyl, halogenated phenyl, C, < 4-alkylphenyl, C1-C4-alkoxyphenyl, nitrophenyl or trifluoromethylphenyl group, an unsubstituted pyridyl or pyrimidyl group ora pyridyl or pyrimidyl group substituted by one or more substituents (which may be the same or different) selected from C1-C4-alkyl groups, C1-C4- alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or
R1 and R2 together with the adjacent nitrogen atoms represent a morpholino, piperidino or pyrrolidino group,
B represents an alkali metal atom, preferably a lithium, sodium or potassium atom, or a monovalent equivalent of zinc, manganese, calcium, magnesium or barium, and
X represents an oxygen or sulphur atom.
As compounds of the general formula I there may be mentioned, for example, the compounds listed in the following Table 1.
Table 1
1-Phenyl-3-(1,2,3-thiadiazol-5-yl)-urea
1 -Phenyl-1 -methyl-3-( I ,2,3-thiadiazol-5-yl)-urea 1 -(4-Chlorophenyl)-3-(1 ,2,3-thiadiazol-5-yl)-urea 1 -Cyclohexyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea 1 -(3-Chlorophenyl)-3-( 1 ,2,3-thiadiazol-5-yl)-urea 1-(4MethyIphenyI)-341 ,2,3-thiadiazol-5-yl)-urea 1 -(3-Methylphenyl)-3-( 1 ,2,3-thiadiazol-5-yl)-urea 1-(3,4-Dichlorophenyl)-3-(1 ,2,3-thiadiazol-5-yl)-urea
1 -Methyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea
1,1 -Dimethyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea 1,1 -Dimethyl-3-methyl-3-(1 ,2,3-thiadiazol-5-yl)-urea 1 -Methyl-3-methyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea
1 -Phenyl-3-(1,2,3-thiadiazol-5-yl)-thiourea
1 -(4-Chlorophenyl)-3-( 1 ,2,3-thiadiazol-5-yl)-thiourea 1 -(2-Pyridyl)-3-( 1 ,2,3-thiadiazol-5-yl)-urea 1 -(5-Chloro-2-pyridyl)-3-( 1 ,2,3-thiadiazol-5-yl)-urea 1 -(4-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1 -(4-Methyl-2-pyrimidyl)-3-( 1 .2,3-thiadiazol-5-yl)-urea 1 -(4-Pyridyl)-3-( 1 ,2,3-thiadiazol-5-yl)-urea
1 -(3-Pyridyl)-3-(1 ,2,3-thiadiazol-5-yI)-urea 1 -(2-Pyrimidyl)-3-( 1 ,2,3-thiadiazol-5-yl)-urea
1 -(3-Methyl-2-pyridyl)-3-(1,2,3-thiadiazol-5-yl)-urea
1 -( 5-Methyl-2-pyridyl)-3-( 1 ,2,3 -thiadi azo I-5-yl)-u rea 1 -(6-Methyl-2-pyridyl)-3-( 1 ,2,3-thiadiazol-5-yl)-urea.
As compounds of the general formula II there may be mentioned, for example, the compounds listed in the following Table 2.
Table 2 5-(Phenylcarbamoylimino)-l ,2,3-thiadiazolin-2-ide, sodium salt xH20
5-(Phenylcarbamoylimino)-1,2,3-thiadiazolin-2-ide, calcium salt x8H20 5-(Phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, potassium salt xH2O 5-(Phenyicarbamoylimino)-l ,2,3-thiadiazolin-2-ide, lithium salt x4H20 5-(Methylphenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, sodium salt xH20 5-(Methylphenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, potassium salt xH2O 5-(Methylphenylcarbamoylimino)-l ,2,3-thiadiazolin-2-ide, lithium salt xH2O 5-(2-Pyridylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide sodium salt x1.5 H20 5-(2-Pyridylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, potassium salt xH2O 5-(2-Pyridylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, lithium salt xH20
5-(Phenylthiocarbamoylimino)-1,2,3-thiadiazolin-2-ide, sodium salt xH2O 5-(Phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, magnesium salt x2H20 5-(Phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, zinc salt x3H20 5-(Phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, manganese salt x3H20 5-(Phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide, barium salt x3H20.
Of these compounds, the following are especially suitable for the preparations and methods of the present invention: 1 -phenyl-3-(1,2,3-thiadiazol-5-yl)-urea, 1 -phenyl- 1 -methyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea, 1 -(2-pyridyl)-3-( 1 ,2,3-thiadiazol-5-yl)-urea and
5-(phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide salts, for example the calcium, magnesium and manganese salts.
The following may be mentioned as substances not, on their own, having any defoliating and/or growth-regulating activity, but being suitable as the basically reactive substances for the preparations and methods of the present invention:
alkali hydroxides, for example sodium and potassium hydroxides,
amines, for example alkylamines, for example triethylamine, alkanolamines, for example diethanolamine, triethanolamine and triisopropanolamine, and hexamethylenetetramine, carbonates, for example sodium carbonate, potassium carbonate and ammonium carbonate,
phosphates, for example tertiary phosphates, for example trisodium phosphate and tripotassium phosphate, and pyrophosphates, for example tetrasodium pyrophosphate and tetrapotassium pyrophosphate,
alkali salts of monocarboxylic acids, for example sodium oleate.
It is preferable to use basically reactive substances that adjust the preparations of the present invention and the mixtures used in the methods of the present invention to a pH-value of more than 8, preferably within the range of from 9.5 to 11.5.
Surprisingly, the mixtures of the defoliating and/or growth-regulating compounds and the basically reactive substances when used according to the present invention have an action that is greater than that of the individual components. They are therefore especially suitable for the defoliation of cotton plants whereby, in an ideal manner, the use of picking machines for boll harvesting is rendered possible.
Other plants can, however, also be advantageously defoliated and/or influenced in their growth, as examples of which there may be mentioned the promotion of bushiness, formation of side-shoots, and inhibition of root growth in the case of grasses and dicotyledons, for example hibiscus, apple trees and other woody plants. Therefore the preparations according to the present invention can be used advantageously both for defoliating plants and also for regulating their growth.
It is known to the man skilled in the art that defoliation is not a herbicidal action and that it is not desired actually to kill the treated plants because the leaves still remain attached to the dead plants and the productive parts of the plant can be damaged. The aim of defoliation, that is to facilitate harvesting and to obtain a purer harvested crop, can be lost as a result of this. It is therefore necessary for the plants to remain alive while the leaves are becoming detached and falling off. This permits the further developments of the productive parts of the plant while the re-growth of new leaves is prevented. The mixtures used in accordance with the present invention achieve all these aims in an advantageous manner so that it can be assumed that the prior art is far exceeded.
The mixture of the defoliating and/or growth-regulating compound and the basically reactive substance in accordance with the present invention can also be used in admixture with other active substances, for example defoliating agents, plant-protecting agents and/or pesticides, depending on the desired purpose. Thus, the preparations of the present invention may contain such further active substances.
The action and the speed of action can also be promoted, for example by action-increasing additives, for example organic solvents, wetting agents and oils. This permits a further decrease in the quantity of the actual active substances used.
The mixture of the defoliating and/or growth-regulating compound and the basically reactive substance in accordance with the present invention is advantageously used in the form of preparations, for example powders, strewable preparations, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers or diluents and, if desired, of surface-active agents, for example wetting, adhesive, emulsifying and/or dispersing agents.
Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, for example benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide, dimethylformamide, and also mineral oil fractions.
Suitable solid carriers are, for example, mineral earths, for example tonsil, silica gel, talcum, kaolin, attaclay, limestone and silicic acid, and vegetable products, for example meals.
As surface-active agents there may be mentioned, for example, sodium or calcium lignin sulphonate, polyoxyethylene-alkylphenyl ethers, naphthalenesulphonic acids and salts thereof, phenolsulphonic acids and salts thereof, formaldehyde condensates, fatty alcohol sulphates, salts of long-chained fatty acids and also substituted benzene-sulphonic acids and salts thereof.
The proportion of the essential constituents, namely the defoliating and/or growth-regulating compound and the basically reactive substance, in the various preparations may vary within wide limits. For example, the preparations of the present invention and the mixtures used in the methods of the present invention may contain approximately from 5 to 95% by weight of these constituents, approximately from 95 to 5% by weight of liquid and/or solid carrier(s) and also, if desired, up to 30% by weight of surface-active agent(s).
The relative ratio by weight of the essential constituents in the various preparations is advantageously approximately 1 part by weight of the compound having a defoliating and/or growthregulating action to 0.5 to 1000 parts by weight of the basically reactive substance, and depends on the sensitivity and resistance of the plants, the time of appiication, the climatic conditions and the soil conditions.
The quantities applied of the mixture of the defoliating and/or growth-regulating compound and the basically reactive substance for the desired defoliation and/or growth-regulating action are generally within the range of from 1 to 10,000 g per hectare, preferably from 10 to 1000 g per hectare.
The mixture of the defoliating and/or growth-regulating compound and the basically reactive substance may be applied in the conventional manner, for example with water as the carrier, in quantities of spray liquor of approximately from 100 to 1000 litres/hectare. It is also possible to apply these mixtures by the so-called "iow-volume" or "ultra-low-volume" method.
The compounds having a defoliating and/or growth-regulating action and the basic additives contained in the preparations of the present invention and in the mixtures used in the methods of the present invention are known per se and may be manufactured according to methods known per se.
For the manufacture of the preparations of the present invention, there may be used, for example, the constituents listed under a), b), c) or d) in the following Table 3, the mixture in each case of course referring to the mixture of the defoliating and/or growth-regulating compound and the basically reactive substance.
Table 3
a) 95% by weight of mixture
4% by weight of kaolin 1 % by weight of surface-active agents based on the sodium salt of N-methyl-N-oleyl-taurine
and the calcium salt of lignin sulphonic acid
b) 80% by weight of mixture
10% by weight of calcium salt of lignin sulphonic acid
3% by weight of ammonium salt of the monosulphuric acid ester of tetraethylene glycol nonyl phenyl ether 7% by weight of colloidal silicic acid
c) 20% by weight of mixture
70% by weight of tonsil
8% by weight of cellulose pitch
2% by weight of wetting agent based on a fatty acid condensation product
d) 5% by weight of mixture
80% by weight of tonsil
10% by weight of cellulose pitch
5% by weight of wetting agent based on a fatty acid condensation product.
The preparations of the present invention are manufactured, for example, by mixing the individual constituents in a drum and then grinding in a mill.
These preparations may be applied either directly or after dilution with water to the plants to be treated. The pH-value of these preparations is of special importance for potentiating the action of the essential components and should advantageously be greater than 8, preferably within the range of from 9.5 to 11.5. It thus represents a special embodiment of the present invention.
The following Examples illustrate the invention. The Examples are based on greenhouse tests that were generally carried out on cotton plants having from 5 to 8 true foliage leaves. The mixtures of the defoliating and/or growth-regulating compound and the basically reactive substance were applied in the form of aqueous preparations based on the compositions described above.
The tests in Examples 1 to 13 were evaluated by counting the number of leaves shed after the application and by calculating the proportion as a percentage of the total number of leaves. In the individual tests, the same number of leaves was always available per test member. The number of leaves per test member varied from test to test between 20 and 28 foliage leaves per test member.
The following Examples 1 to 13 contain information on the active substance, basically reactive substance, mixture, quantity applied, and the percentage defoliation determined. In some cases there is indicated in brackets after the percentage defoliation obtained by the combinations, the value calculated according to the method described by S. R. Colby which would be expected in the case of an additive action [S. R. Colby "Calculating Synergistic and Antagonistic Responses of Herbicide
Combinations" Weeds 1 5/1(1967) p. 20-22].
This calculation was'made according to the following equation: --XY
E=X+Y 100
in which X=percentage defoliation with substance A using p kg of active substance/ha
Y=percentage defoliation with substance B using q kg of active substance/ha
E=expected defoliation by A+B using p+q kg/ha.
If the value observed is greater than the value E calculated according to Colby then the
combination has a synergistic action. The results of Examples 1 to 1 3 clearly show the potentiation of
action of the substance having a defoliating action by the basically reactive substances that are
themselves inactive as defoliants.
Example 1
Young cotton plants at the stage of having 5 foliage leaves were treated in a series of tests with
the mixtures indicated in the Table below and with the individual components of the mixtures, namely the active substance and the basically reactive substance (repeated 4 times). The quantity of water
used as carrier was 500 litres/ha. After a few days the percentage of shed leaves was determined. The
results are given in the following Table:
Application
quantity Defoliation E (according
Components in g/ha as a % to Colby)
1-phenyl-3-(1,2,3- 80 35
thiadiazol-5-yl)
urea=l K2CO3=ll 500 0 K4P207=lll 500 0 1+11 80+500 70 (35)
1+111 80+500 60 (35)
Example 2
Young cotton plants were treated as indicated in Example 1. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components in g/ha as a % to Colby)
1-phenyl-3-(1,2,3- 80 57
thiadiazol-5-yl)
urea=l K2CO3=ll 500 0
Na2CO3=XV 500 0
(NH4)2CO3=lV 500 0
KOH=V 500 0
1+11 80+500 70 (57)
I+XV 80+500 85 (57)
I+IV 80+500 80 (57)
I+V 80+500 60 (57)
Example 3
Young cotton plants were treated as indicated in Example 1. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components ing/ha as a % to Colby) 1-phenyl-3-(1,2,3- 40 29 thiadiazol-5-yl)- urea=l
Na-oleate=VI 500 0 triethanolamine=VIl 500 0 triethyiamine=VIII 500 0 I+VI 40+500 33 (29) I+Vll 40+500 43 (29) l+VIll 40+500 62 (29)
Example 4
Young cotton plants were treated as indicated in Example 1. The lower percentage action compared with the above Examples can be attributed to unfavourable environmental conditions when
the tests were carried out in the winter months. The results are given in the following Table.
Application
quantity Defoliation
Components in glha as a 1 -phenyl-3-(1,2,3- 80 0 thiadiazol-5-yl)urea=l
K2CO3=ll 500 0
1,000 0
1+11 80+500 29
5-(phenyl-carbamoyl- 80 0 imino)-l 2,3- thiadiazolin-2-ide,
calcium salt=IX
IX+II 80+500 24 1-(2-pyridyl)-3- 80 0 (1 ,2,3-thiadiazol-5-yl)-
urea=X X+ll 80+500 23.5
Example 5
Young cotton plants were treated as indicated in Example 4. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components in glha as a % to Colby) 5-(phenylcarbamoyl- 500 17 imino)-1 '2,3- thiadiazolin-2-ide,
potassium salt=XI K2C03=lI 500 0 Xl+ll 500+500 39 (17)
Example 6
Young hibiscus plants each having from 7 to 10 unfolded leaves were treated as indicated in
Example 1. The percentage of shed leaves was determined 6 days after the treatment.
Application
quantity Defoliation E (according
Components in g/ha as a % to Colby) 1-phenyl3-(1,2,3- 2.5 0 thiadiazol-5-yl)- 10 4 urea=l K2CO > =I I 500 0 K4P207=lll 500
1+11 2.5+500 14 (O) 10+500 46 (4)
1+111 2.5+500 11 (O) 10+500 54 (4)
Example 7
Young cotton plants were treated as indicated in Example 1. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components ing/ha as a % to Colby)
1-phenyl-3-(1,2,3- 40 19 thiadiazol-5-yl)- urea=l K2CO3=ll 3000 0 K4P207=lil 3000 0
1+11 40+300 57 (19)
40+1000 67 (19)
40+3000 71 (19)
40+10000 76 (19)
1+111 40+1000 62 (19)
40+3000 86 (19) 40+10000 90 (19)
Example 8
Young cotton plants were treated as indicated in Example 1. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components in g/ha as a % to Colbyl 1-phenyl-3-(1,2,3- 40 33
thiadiazol-5-yl)
urea=l K2CO3=l l 540 0
hexamethylene- 540 0 tetra min e=XVI 1+11 40+500 71 (33) l+XVl 40+500 48 (33)
Example 9
Young cotton plants were treated as indicated in Example 1. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components ing/ha as a % to Colby)
1-phenyl-3-(1,2,3- 40 64
thiadiazol-5-yl)
urea=l
K2CO3=ll 500 0
K3PO4=XVII 500 0
I+II 40+500 86 (64)
I+XVII 40+500 91 (64)
Example 10
Young cotton plants were treated as indicated in Example 1. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components ing/ha as a % to Colby)
1-phenyl-1-methyl- 40 63
3-(1,2,3-thiadiazol 5-yl)-urea=Xll K2CO3=l l 500 0
K3PO4=XVII 500 0 Xil+ll 40+500 71 (63) Xll+XVll 40+500 76 (63)
Example 11
Young cotton plants were treated as indicated in Example 1. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components in g/ha as a % to Colby)
5-(phenylcarbamoyl- 40 52
imino)-1,2,3
thiadiazolin-2-ide,
magnesium salt=XIII K3PO4=XVII 500 0 Xlil+XVII 40+500 71 (52)
Example 12
Young cotton plants were treated as indicated in Example 1. The results are given in the following
Table.
Application
quantity Defoliation E (according
Components in g/ha as a % to Colby)
5-(phenylcarbamoyl- 40 32
imino)-1,2,3
thiadiazolin-2-ide,
manganese salt=XIV K3PO4=XVII 500 0
XIV+XVII 40+500 82 (32)
Example 13
Young cotton plants having from 21 to 27 leaves were treated as indicated in Example 1. The results are given in the following Table.
Application
quantity Defoliation
Components in g/ha as a
1-phenyl-3-(1,2,3- 300 19
thiadiazol-5-yl)
urea=l K2C03=ll 1000 0
1+11 300+1000 48
Example 14
In a series of tests young Urtica urens plants were sprayed with the mixture according to the present invention indicated in the Table below and with the individual components of the mixture.
Three weeks later the fresh weight of the parts of the plants above the soil was determined. The following Table gives the relative values for plant height and the fresh weight (untreated=1 00). As compared with the untreated control plants, the treated plants had the desired more compact, lower and therefore more stable growth. Their fresh weight was nevertheless greater. The results of the tests show that the mixture according to the present invention brings about a greater growth-regulating action than the individual components.
Application Relative Relative
concentration plant fresh
Components in ppm height weight
1-phenyl-3-(1,2,3- 2 79 113
thiadiazol-5-yl)
urea=l KzCO3=ll 26 100 100
1+11 2+26 75 131
Claims (101)
1. A preparation for defoliating and/or ragulating the growth of plants, which comprises a defoliating and/or growth-regulating compound selected from 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives, in admixture or conjunction with a basically reactive substance.
2. A preparation as claimed in claim 1, wherein the defoliating and/or growth-regulating compound is a 1 ,2,3-thiadiazol-5-yl-urea derivative of the general formula í
in which
R1 represents a hydrogen atom or a C1-C5-alkyl group,
R2 represents a C1-C5-alkyl group, a C5-C8-cycloalkyl group, a phenyl, halogenated phenyl, C1-C4-a Ikylphenyl, CaC4-alkoxyphenyl, nitrophenyl or trifluoromethylphenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyrimidyl group substituted by one or more substituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or
R, and R2 together with the adjacent nitrogen atoms represent a morpholino, piperidino or pyrrolidino group,
R3 represents a hydrogen atom or a C,Cs-alkyl group, and
X represents an oxygen or sulphur atom.
3. A preparation as claimed in claim 2, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is any one of the compounds listed in Table 1 herein.
4. A preparation as claimed in claim 2, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is 1 phenyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea.
5. A preparation as claimed in claim 2, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is 1 phenyl-1 -methyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea.
6. A preparation as claimed in claim 2, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is 1 -(2 pyridyl)-3-( 1 ,2,3-thiadiazol-5-yl)-u rea.
7. A preparation as claimed in claim 1, wherein the defoliating and/or growth-regulating compound is a 1 ,2,3-thiadiazolin-2-ide derivative of the general formula II
in which
R, represents a hydrogen atom or a C1C5-aIkyl group, R2 represents a hydrogen atom, a C1 C 5-alkylgroup, a aC5-C8-cycloalkyl group, a phenyl, halogenated phenyl, C1-C4--alkylphenyl, C1C4-alkoxyphenyl, nitrophenyl or trifluoromethylphenyl group, an unsubstituted pyridyl or pyrimidyl group or a pyridyl or pyrimidyl group substituted by one or more substituents selected from C14-alkyl groups, C1-C4-alkoxy groups, halogen atoms, nitro groups and trifluoromethyl groups, or
R1 and R2 together with the adjacent nitrogen atom represent a morpholino, piperidino or pyrrolidino group,
B represents an alkali metal atom or a monovalent equivalent of zinc, manganese, calcium, magnesium or barium, and
X represents an oxygen or sulphur atom.
8. A preparation as claimed in claim 7, wherein B represents a lithium, sodium or potassium atom.
9. A preparation as claimed in claim 7, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is any one of the compounds listed in Table 2 herein.
10. A preparation as claimed in claim 7, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the calcium salt of 5-(phenylcarbamoylimino)- 1 ,2,3-thiadiazolin-2-ide.
11. A preparation as claimed in claim 7, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 5-(phenylcarbamoylimino)-l ,2,3-thiadiazolin-2-ide.
12. A preparation as claimed in claim 7, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the manganese salt of 5-(phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide.
13. A preparation as claimed in any one of claims 1 to 12, wherein the basically reactive substance is an alkali hydroxide, an amine, a carbonate, a phosphate or an alkali salt of a monocarboxylic acid.
14. A preparation as claimed in claim 13, wherein the alkali hydroxide is sodium or potassium hydroxide.
15. A preparation as claimed in claim 13, wherein the amine is triethylamine, diethanolamine, triethanolamine, triisopropanolamine or hexamethylenetetramine.
16. A preparation as claimed in claim 13, wherein the carbonate is sodium carbonate, potassium carbonate or ammonium carbonate.
1 7. A preparation as claimed in claim 13, wherein the phosphate is trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate or tetrapotassium pyrophosphate.
18. A preparation as claimed in claim 13, wherein the alkali salt of a monocarboxylic acid is sodium oleate.
19. A preparation as claimed in claim 1, which comprises 1 -phenyl-3-(1 ,2,3-thiadiazol-5-yl)-urea as the defoliating and/or growth-regulating compound in admixture with potassium hydroxide, potassium carbonate, ammonium carbonate, tetrapotassium pyrophosphate, triethylamine, triethanolamine or sodium oleate as the basically reactive substance.
20. A preparation as claimed in claim 1, which comprises 1 -(2-pyridyl)-3-( 1 ,2,3-thiadiazol-5-yl)- urea as the defoliating and/or growth-regulating compound in admixture with potassium carbonate as the basically reactive substance.
21. A preparation as claimed in claim 1, which comprises the calcium salt of 5 (phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide as the defoliating and/or growth-regulating compound in admixture with potassium carbonate as the basically reactive substance.
22. A preparation as claimed in any one of claims 1 to 21, wherein the ratio by weight of the defoliating and/or growth-regulating compound to the basically reactive substance is within the range of from 1:0.5 to 1:1000.
23. A preparation as claimed in any one of claims 1 to 22, having a pH-value greater than 8.
24. A preparation as claimed in claim 23, having a pH-value within the range of from 9.5 to 11.5.
25. A preparation as claimed in any one of claims 1 to 24, which also contains a liquid carrier and/or a solid carrier.
26. A preparation as claimed in claim 25, containing 5 to 95% by weight of the defoliating and/or growth-regulating compound and the basically reactive substance and 95 to 5% by weight of the liquid and/or solid carrier(s).
27. A preparation as claimed in any one of claims 1 to 26, which also contains a surface-active agent.
28. A preparation as claimed in claim 27, containing the surface-active agent in an amount of up to 30% by weight.
29. A preparation as claimed in any one of claims 1 to 28, which also contains one or more active substances selected from defoliating agents, plant-protecting agents and pesticides other than 1,2,3- thiadiazol-5-yi-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives.
30. A preparation as claimed in any one of claims 1 to 29, which is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension.
31. Any one of the preparations substantially as described in Table 3 herein.
32. Any one of the preparations as claimed in claim 1 and substantially as described in Examples
1 to 14 herein.
33. A pack which comprises a preparation as claimed in any one of claims 1 to 32, together with instructions for its use for defoliating and/or regulating the growth of living plants.
34. A method of defoliating and/or regulating the growth of a living plant, wherein the living plant is treated with a mixture comprising (i) a defoliating and/or growth-regulating compound selected from 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives and (ii) a basically reactive substance.
35. A method as claimed in claim 34, wherein the defoliating and/or growth-regulating compound is a 1 ,2,3-thiadiazol-5-yl-urea derivative of the general formula I given in claim 2, in which R1,R2, R3 and X have the meanings given in claim 2.
36. A method as claimed in claim 35, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is any one of the compounds listed in Table 1 herein.
37. A method as claimed in claim 35, wherein the 1 ,2.3-thiadiazol-5-yl-urea derivative is 1 phenyl-3-(1 ,2,3-thiadiazol-5-yl)-urea.
38. A method as claimed in claim 35, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is 1 phenyl-1 -methyl-3-(1 ,2,3-thiadiazol-5-yl)-urea.
39. A method as claimed in claim 35, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is 1-(2 pyridyl)-3-( 1 ,2,3-thiadiazol-5-yl )-urea.
40. A method as claimed in claim 34, wherein the defoliating and/or growth-regulating compound is a 1 ,2,3-thiadiazolin-2-ide derivative of the general formula II given in claim 7, in which R1, R2,B and X have the meanings given in claim 7.
41. A method as claimed in claim 40, wherein B represents a lithium, sodium or potassium atom.
42. A method as claimed in claim 40, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is any one of the compounds listed in Table 2 herein.
43. A method as claimed in claim 40, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the calcium salt of 5-(phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide.
44. A method as claimed in claim 40, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 5-(phenylcarbamoylimino)- 1 ,2,3-thiadiazolin-2-ide.
45. A method as claimed in claim 40, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the manganese salt of 5-(phenylcarbamoylimino)- 1 ,2,3-thiadiazolin-2-ide.
46. A method as claimed in any one of claims 34 to 45, wherein the basically reactive substance is an alkali hydroxide, an amine, a carbonate, a phosphate or an alkali salt of a monocarboxylic acid.
47. A method as claimed in claim 46, wherein the alkali hydroxide is sodium or potassium hydroxide.
48. A method as claimed in claim 46, wherein the amine is triethylamine, diethanolamine, triethanolamine, triisopropanolamine or hexamethylenetetramine.
49. A method as claimed in claim 46, wherein the carbonate is sodium carbonate, potassium carbonate or ammonium carbonate.
50. A method as claimed in claim 46, wherein the phosphate is trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate or tetrapotassiu m pyrophosphate.
51. A method as claimed in claim 46, wherein the alkali salt of a monocarboxylic acid is sodium oleate.
52. A method as claimed in claim 34, wherein the mixture is a mixture comprising 1-phenyl-3 (1 ,2,3-thiadiazol-5-yl)-urea and potassium hydroxide, potassium carbonate, ammonium carbonate, tetrapotassium pyrophosphate, triethylamine, triethanolamine or sodium oleate.
53. A method as claimed in claim 34, wherein the mixture is a mixture comprising 1-(2-pyridyl)- 3-(1 ,2,3-thiadiazol-5-yl)-urea and potassium carbonate.
54. A method as claimed in claim 34, wherein the mixture is a mixture comprising the calcium salt of 5-(phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide and potassium carbonate.
55. A method as claimed in any one of claims 34 to 54, wherein the ratio by weight of the defoliating and/or growth-regulating compound to the basically reactive substance in the mixture is within the range of from 1:0.5 to 1:1000.
56. A method as claimed in any one of claims 34 to 55, wherein the pH-value of the mixture is greater than 8.
57. A method as claimed in claim 56, wherein the pH-value of the mixture is within the range of from 9.5 to 11.5.
58. A method as claimed in any one of claims 34 to 57, wherein the mixture also contains a liquid carrier and/or a solid carrier.
59. A method as claimed in claim 58, wherein the mixture contains 5 to 95% by weight of the defoliating and/or growth-regulating compound and the basically reactive substance and 95 to 5% by weight of the liquid and/or solid carrier(s).
60. A method as claimed in any one of claims 34 to 59, wherein the mixture also contains a surface-active agent.
61. A method as claimed in claim 60, wherein the mixture contains up to 30% by weight of the surface-active agent.
62. A method as claimed in any one of claims 34 to 61, wherein the mixture also contains one or more active substances selected from defoliating agents, plant-protecting agents and pesticides other than 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives.
63. A method as claimed in any one of claims 34 to 62, wherein the mixture is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension.
64. A method as claimed in claim 34, wherein the mixture is any one of the preparations substantially as described in Table 3 herein.
65. A method as claimed in claim 34, conducted substantially as described herein.
66. A method as claimed in claim 34, conducted substantially as described in Example 14 herein.
67. A method of defoliating and/or regulating the growth of plants in a crop area, wherein the crop area is treated with a mixture comprising (i) a defoliating and/or growth-regulating compound selected from 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives and (ii) a basically reactive substance.
68. A method as claimed in claim 67, wherein the defoliating and/or growth-regulating compound is a 1 ,2,3-thiadiazol-5-yl-urea derivative of the general formula I given in claim 2, in which
R,, R2, R3 and X have the meanings given in claim 2.
69. A method as claimed in claim 68, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is any one of the compounds listed in Table 1 herein.
70. A method as claimed in claim 68, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is 1 phenyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea.
71. A method as claimed in claim 68, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is 1 phenyl- 1 -methyl-3-( 1 ,2,3-thiadiazol-5-yl)-urea.
72. A method as claimed in claim 68, wherein the 1 ,2,3-thiadiazol-5-yl-urea derivative is 1-(2 pyridyl)-3-( 1,2,3 1 ,2,3-thiadiazol-5-yl)-urea.
73. A method as claimed in claim 67, wherein the defoliating and/or growth-regulating compound is a 1 ,2,3-thiadiazolin-2-ide derivative of the general formula II given in claim 7, in which Rt, R2, B and X have the meanings given in claim 7.
74. A method as claimed in claim 73, wherein B represents a lithium, sodium or potassium atom.
75. A method as claimed in claim 73, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is any one of the compounds listed in Table 2 herein.
76. A method as claimed in claim 73, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the calcium salt of 5-(phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide.
77. A method as claimed in claim 73, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the magnesium salt of 5-(phenylcarbamoylimino)-l ,2,3-thiadiazolin-2-ide.
78. A method as claimed in claim 73, wherein the 1 ,2,3-thiadiazolin-2-ide derivative is the manganese salt of 5-(phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide.
79. A method as claimed in any one of claims 67 to 78, wherein the basically reactive substance is an alkali hydroxide, an amine, a carbonate, a phosphate or an alkali salt of a monocarboxylic acid.
80. A method as claimed in claim 79, wherein the alkali hydroxide is sodium or potassium hydroxide
81. A method as claimed in claim 79, wherein the amine is triethylamine, diethanolamine, triethanolamine, triisopropanolamine or hexamethylenetetramine.
82. A method as claimed in claim 79, wherein the carbonate is sodium carbonate, potassium carbonate or ammonium carbonate.
83. A method as claimed in claim 79, wherein the phosphate is trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate or tetrapotassium pyrophosphate.
84. A method as claimed in claim 79, wherein the alkali salt of a monocarboxylic acid is sodium oleate.
85. A method as claimed in claim 67, wherein the mixture is a mixture comprising 1-phenyl-3 (1 ,2,3-thiadiazoi-5-yl)-urea and potassium hydroxide, potassium carbonate, ammonium carbonate, tetrapotassiu m pyrophosphate, triethylamine, triethanolamine or sodium oleate.
86. A method as claimed in claim 67, wherein the mixture is a mixture comprising 1 -(2-pyridyl)3-(1 ,2,3-thiadiazol-5-yl)-urea and potassium carbonate.
87. A method as claimed in claim 67, wherein the mixture is a mixture comprising the calcium salt of 5-(phenylcarbamoylimino)-1 ,2,3-thiadiazolin-2-ide and potassium carbonate.
88. A method as claimed in any one of claims 67 to 87, wherein the ratio by weight of the defoliating and/or growth-regulating compound to the basically reactive substance in the mixture is within the range of from 1:0.5 to 1:1000.
89. A method as claimed in any one of claims 67 to 88, wherein the pH-value of the mixture is greater than 8.
90. A method as claimed in claim 89, wherein the pH-value of the mixture is within the range of from 9.5 to 11.5.
91. A method as claimed in any one of claims 67 to 90, wherein the mixture also contains a liquid carrier and/or a solid carrier.
92. A method as claimed in claim 91, wherein the mixture contains 5 to 95% by weight of the defoliating and/or growth-regulating compound and the basically reactive substance and 95 to 5% by weight of the liquid and/or solid carrier(s).
93. A method as claimed in any one of claims 67 to 92, wherein the mixture also contains a surface-active agent.
94. A method as claimed in claim 93, wherein the mixture contains up to 30% by weight of the surface-active agent.
95. A method as claimed in any one of claims 67 to 94, wherein the mixture also contains one or more active substances selected from defoliating agents, plant-protecting agents and pesticides other than 1 ,2,3-thiadiazol-5-yl-urea derivatives and 1 ,2,3-thiadiazolin-2-ide derivatives.
96. A method as claimed in any one of claims 67 to 95, wherein the mixture is in the form of a powder, a strewable preparation, a solution, an emulsion or a suspension.
97. A method as claimed in claim 67, wherein the mixture is any one of the preparations substantially as described in Table 3 herein.
98. A method as claimed in any one of claims 67 to 97, wherein the total amount of the defoliating and/or growth-regulating compound and the basically reactive substance used for the treatment is within the range of from 1 to 10,000 grams per hectare.
99. A method as claimed in claim 98, wherein the total amount is within the range of from 10 to 1000 grams per hectare.
100. A method as claimed in any one of claims 87 to 99, wherein the crop area contains cotton plants.
101. A method as claimed in claim 67, conducted substantially as described herein.
1 02. A method as claimed in claim 67, conducted substantially as described in any one of
Examples 1 to 13 herein.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803040902 DE3040902A1 (en) | 1980-10-27 | 1980-10-27 | MEANS, IN PARTICULAR, FOR THE DEBELING OF PLANTS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2086228A true GB2086228A (en) | 1982-05-12 |
| GB2086228B GB2086228B (en) | 1983-12-21 |
Family
ID=6115564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8132217A Expired GB2086228B (en) | 1980-10-27 | 1981-10-26 | Preparations for defoliating and/or regulating the growth of plants and their use |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5799504A (en) |
| KR (1) | KR830007606A (en) |
| AT (1) | AT380624B (en) |
| AU (1) | AU550920B2 (en) |
| BE (1) | BE890871A (en) |
| BG (1) | BG37071A3 (en) |
| BR (1) | BR8106908A (en) |
| CA (1) | CA1165580A (en) |
| CH (1) | CH647928A5 (en) |
| CS (1) | CS221995B2 (en) |
| DD (1) | DD201560A5 (en) |
| DE (1) | DE3040902A1 (en) |
| DK (1) | DK440481A (en) |
| EG (1) | EG15216A (en) |
| FI (1) | FI65531C (en) |
| FR (1) | FR2492632B1 (en) |
| GB (1) | GB2086228B (en) |
| GR (1) | GR74697B (en) |
| HU (1) | HU188555B (en) |
| IE (1) | IE51687B1 (en) |
| IL (1) | IL64096A (en) |
| IN (1) | IN157368B (en) |
| IT (1) | IT1139268B (en) |
| LU (1) | LU83705A1 (en) |
| MA (1) | MA19312A1 (en) |
| NL (1) | NL8104620A (en) |
| NZ (1) | NZ198660A (en) |
| PH (1) | PH18494A (en) |
| PL (1) | PL127943B1 (en) |
| RO (1) | RO84304B (en) |
| SE (1) | SE448143B (en) |
| SU (1) | SU1245252A3 (en) |
| TR (1) | TR21352A (en) |
| ZA (1) | ZA817446B (en) |
| ZW (1) | ZW25981A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015107336A1 (en) * | 2014-01-14 | 2015-07-23 | Crop Intellect Ltd. | Agrochemical composition comprising a ν,ν'-disubstituted (thio)urea for the improvement of crop productivity |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2506690A1 (en) * | 1975-02-14 | 1976-09-02 | Schering Ag | Means for removing leaves from plants |
| DE2719810A1 (en) * | 1977-04-28 | 1978-11-02 | Schering Ag | 1,2,3-THIADIAZOLINE-2-ID DERIVATIVES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THEIR CONTAINING AGENTS WITH GROWTH REGULATORY EFFECT FOR PLANTS |
-
1980
- 1980-10-27 DE DE19803040902 patent/DE3040902A1/en not_active Withdrawn
-
1981
- 1981-09-28 SU SU813360509A patent/SU1245252A3/en active
- 1981-10-05 DK DK440481A patent/DK440481A/en not_active Application Discontinuation
- 1981-10-09 NL NL8104620A patent/NL8104620A/en not_active Application Discontinuation
- 1981-10-12 IN IN653/DEL/81A patent/IN157368B/en unknown
- 1981-10-15 NZ NZ198660A patent/NZ198660A/en unknown
- 1981-10-19 FI FI813262A patent/FI65531C/en not_active IP Right Cessation
- 1981-10-21 IT IT24600/81A patent/IT1139268B/en active
- 1981-10-21 DD DD81234265A patent/DD201560A5/en unknown
- 1981-10-22 FR FR8119817A patent/FR2492632B1/en not_active Expired
- 1981-10-22 LU LU83705A patent/LU83705A1/en unknown
- 1981-10-22 CS CS817744A patent/CS221995B2/en unknown
- 1981-10-22 CA CA000388500A patent/CA1165580A/en not_active Expired
- 1981-10-22 IL IL64096A patent/IL64096A/en unknown
- 1981-10-23 AT AT0454481A patent/AT380624B/en not_active IP Right Cessation
- 1981-10-23 IE IE2485/81A patent/IE51687B1/en unknown
- 1981-10-23 JP JP56168862A patent/JPS5799504A/en active Pending
- 1981-10-23 CH CH6799/81A patent/CH647928A5/en not_active IP Right Cessation
- 1981-10-23 PL PL1981233556A patent/PL127943B1/en unknown
- 1981-10-23 GR GR66348A patent/GR74697B/el unknown
- 1981-10-26 BE BE0/206350A patent/BE890871A/en not_active IP Right Cessation
- 1981-10-26 TR TR21352A patent/TR21352A/en unknown
- 1981-10-26 SE SE8106300A patent/SE448143B/en not_active IP Right Cessation
- 1981-10-26 BG BG053942A patent/BG37071A3/en unknown
- 1981-10-26 HU HU813141A patent/HU188555B/en unknown
- 1981-10-26 BR BR8106908A patent/BR8106908A/en unknown
- 1981-10-26 GB GB8132217A patent/GB2086228B/en not_active Expired
- 1981-10-27 RO RO105654A patent/RO84304B/en unknown
- 1981-10-27 AU AU76849/81A patent/AU550920B2/en not_active Ceased
- 1981-10-27 ZW ZW259/81A patent/ZW25981A1/en unknown
- 1981-10-27 KR KR1019810004089A patent/KR830007606A/en not_active Ceased
- 1981-10-27 PH PH26406A patent/PH18494A/en unknown
- 1981-10-27 ZA ZA817446A patent/ZA817446B/en unknown
- 1981-10-27 EG EG624/81A patent/EG15216A/en active
- 1981-10-27 MA MA19514A patent/MA19312A1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015107336A1 (en) * | 2014-01-14 | 2015-07-23 | Crop Intellect Ltd. | Agrochemical composition comprising a ν,ν'-disubstituted (thio)urea for the improvement of crop productivity |
| US9949486B2 (en) | 2014-01-14 | 2018-04-24 | Crop Intellect Ltd. | Agrochemical composition comprising a N,N#-disubstituted (thio)urea for the improvement of crop productivity |
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