CA2048275A1 - Synergistic agents for regulating plant growth - Google Patents
Synergistic agents for regulating plant growthInfo
- Publication number
- CA2048275A1 CA2048275A1 CA002048275A CA2048275A CA2048275A1 CA 2048275 A1 CA2048275 A1 CA 2048275A1 CA 002048275 A CA002048275 A CA 002048275A CA 2048275 A CA2048275 A CA 2048275A CA 2048275 A1 CA2048275 A1 CA 2048275A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkoxy
- salts
- methyl
- plant growth
- 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.)
- Abandoned
Links
- 230000008635 plant growth Effects 0.000 title claims description 7
- 230000001105 regulatory effect Effects 0.000 title claims description 7
- 239000012747 synergistic agent Substances 0.000 title description 2
- -1 1, 3-butadiene-1,4-diyl group Chemical group 0.000 claims abstract description 119
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 230000002195 synergetic effect Effects 0.000 claims abstract description 15
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 11
- 239000000654 additive Substances 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract 7
- 125000002636 imidazolinyl group Chemical group 0.000 claims abstract 4
- 230000012010 growth Effects 0.000 claims description 44
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 229920000742 Cotton Polymers 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 235000013339 cereals Nutrition 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 2
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical class C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 claims description 2
- VHOVSQVSAAQANU-UHFFFAOYSA-M mepiquat chloride Chemical compound [Cl-].C[N+]1(C)CCCCC1 VHOVSQVSAAQANU-UHFFFAOYSA-M 0.000 claims 4
- JUZXDNPBRPUIOR-UHFFFAOYSA-N chlormequat Chemical class C[N+](C)(C)CCCl JUZXDNPBRPUIOR-UHFFFAOYSA-N 0.000 claims 3
- NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical class C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- BABDBQPWZQXOOR-UHFFFAOYSA-N 1,1-dimethyldiazinan-1-ium Chemical class C[N+]1(C)CCCCN1 BABDBQPWZQXOOR-UHFFFAOYSA-N 0.000 claims 1
- GARJMFRQLMUUDD-UHFFFAOYSA-N 1,1-dimethylpyrrolidin-1-ium Chemical class C[N+]1(C)CCCC1 GARJMFRQLMUUDD-UHFFFAOYSA-N 0.000 claims 1
- 150000002462 imidazolines Chemical class 0.000 claims 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000004438 haloalkoxy group Chemical group 0.000 abstract description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 125000004995 haloalkylthio group Chemical group 0.000 abstract description 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 48
- 239000000460 chlorine Substances 0.000 description 25
- 239000002689 soil Substances 0.000 description 25
- 238000009331 sowing Methods 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 239000004615 ingredient Substances 0.000 description 20
- 230000008654 plant damage Effects 0.000 description 20
- 238000011156 evaluation Methods 0.000 description 18
- 238000011282 treatment Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- 241000209140 Triticum Species 0.000 description 15
- 235000021307 Triticum Nutrition 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 235000017168 chlorine Nutrition 0.000 description 14
- 229940060038 chlorine Drugs 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 238000003359 percent control normalization Methods 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 12
- 241000219146 Gossypium Species 0.000 description 11
- 241000209219 Hordeum Species 0.000 description 11
- 235000007340 Hordeum vulgare Nutrition 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
- 239000004927 clay Substances 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000004201 L-cysteine Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 239000003630 growth substance Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000004576 sand Substances 0.000 description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 4
- YSMODUONRAFBET-UHFFFAOYSA-N 5-hydroxylysine Chemical group NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 3
- 125000004710 2-methylpropylthio group Chemical group CC(CS*)C 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241001024304 Mino Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 2
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 2
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- 125000004794 2-chloro-2-fluoroethoxy group Chemical group ClC(CO*)F 0.000 description 2
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 241000283014 Dama Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241001522316 Pyrrhula pyrrhula Species 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004788 dichlorofluoromethoxy group Chemical group ClC(O*)(F)Cl 0.000 description 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
- JNSGIVNNHKGGRU-JYRVWZFOSA-N diethoxyphosphinothioyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOP(=S)(OCC)OC(=O)C(=N/OC)\C1=CSC(N)=N1 JNSGIVNNHKGGRU-JYRVWZFOSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- 230000005070 ripening Effects 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 230000009105 vegetative growth Effects 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- DARPYRSDRJYGIF-PTNGSMBKSA-N (Z)-3-ethoxy-2-naphthalen-2-ylsulfonylprop-2-enenitrile Chemical compound C1=CC=CC2=CC(S(=O)(=O)C(\C#N)=C/OCC)=CC=C21 DARPYRSDRJYGIF-PTNGSMBKSA-N 0.000 description 1
- SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical class OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- 125000004912 1-ethylbutylamino group Chemical group C(C)C(CCC)N* 0.000 description 1
- 125000004790 1-fluoroethoxy group Chemical group FC(C)O* 0.000 description 1
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- 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
- LMCBYQIBQXKCLN-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid;naphthalene Chemical compound C1=CC=CC2=CC=CC=C21.C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 LMCBYQIBQXKCLN-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical class NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
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- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical group [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 1
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- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004897 3-methylbutylamino group Chemical group CC(CCN*)C 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000004904 3-methylpentylamino group Chemical group CC(CCN*)CC 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- 125000000205 L-threonino group Chemical group [H]OC(=O)[C@@]([H])(N([H])[*])[C@](C([H])([H])[H])([H])O[H] 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical class CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 101100313003 Rattus norvegicus Tanc1 gene Proteins 0.000 description 1
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- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 1
- 125000004787 chlorofluoromethoxy group Chemical group ClC(O*)F 0.000 description 1
- 208000037516 chromosome inversion disease Diseases 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006006 difluoroethoxy group Chemical group 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 235000021038 drupes Nutrition 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000002015 leaf growth Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 235000021039 pomes Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cultivation Of Plants (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
O.Z. 0050/41834 Abstract of the Disclosure: Plant growth regulators contain a synergistic mixture of one or more growth-regulating quaternary anunonium salts and an imidazolinyl derivative of the general formula II
II
where R1 is alkyl, R2 is alkyl or cycloalkyl, R3 is hydrogen, hydroxyl, alkyl, alkoxy, alkylamino, dialkylamino or unsubstituted or substitutd phenyl, phenoxy or phenylamino, R4 is hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio and R5 and R6 independently of one another are each one of the groups stated for R4 or together form an unsubstituted or substituted 1, 3-butadiene-1,4-diyl group, and inert additives.
II
where R1 is alkyl, R2 is alkyl or cycloalkyl, R3 is hydrogen, hydroxyl, alkyl, alkoxy, alkylamino, dialkylamino or unsubstituted or substitutd phenyl, phenoxy or phenylamino, R4 is hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio and R5 and R6 independently of one another are each one of the groups stated for R4 or together form an unsubstituted or substituted 1, 3-butadiene-1,4-diyl group, and inert additives.
Description
7 ~
O.Z. 0050/41834 Synerqistic aqents for requla~in~ ~lant qrowth The present invention relates to agent~ for regulating plant growth, containing a synergistic mixture of one or more growth-ragulating qua~ernaxy ammonium salts from the group consis~ing o~ the compounds I, comprising N,N-dLmethylazacycloheptani~m salt~, N,N
dimethylpipexidinium salts, N,N~dimethyltetrahydro-pyridazinium salts, N,N,N-trimethyl-N-~-chloroethyl-ammonium salts~ N-methylpyridinium salts and N,N-dLme-thylpyrrolidinium salts, and an imiclazolinyl derivativeof ~he ~eneral formula II
R 5~COR 3 I I
R 6 N~R 1 HN O
wh~re R1 i~ Cl-C4-alkyl, R2 i~ Cl-C4-alkyl or C3-C~ CYC1G_ alkyl, R3 iS ~ydrogen, hydro~yl, Cl-Cl2-alkyl, Cl-Cl2-alkoxy, C1-C1~-alkylamino, di-Cl-Cl2-alXylamino or is phenyl t phenoxy or ph~nylamino, where the aromatic radicals may carry from one ~o five halogen atoms and/vr from one to three of the following group~: Cl-C4-alkyl ~
Cl-C4-haloalkyl, Cl-C4-alkoxy, C~-C4-haloalko~r, C~ 4-alXylthio or C1-C4-haloalkylthio, R4 is hydrogen, halogen?
Cl-C4-alkyl, Cl-C4-haloallcyl, Cl-C,,-alkoxy, Cl-C4-haloalkoxy, Cl~C4-alkylthio or C1-C4-haloalkylthio and ~5 and R~ lndepend~ntly of one another are each one of the group~ ~tated for R4 or together form a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atomsand/or from one to three of the following groups: C1-C4-alkyl r C1-C4-haloalkyl, Cl-C4-alkoxy, Cl~C4 haloalko:~y, Cl-C4-alkylthio or Cl-C4-haloal~ylthio, and inert additives.
The present invention furthermore relates to methods ~or regulating plant growth with these agents.
~ uaternary ammonium compound~ are disclosed in the literature as plant growth regulators (DE-A 22 07 575). The li~erature alco describes 'j ,~ ~" ~
- Z - O.Z. 0050~41834 imidazole deriYatives as herbicides ~DE-A 31 21 736).
Mixtures of N,N,N-trimethyl-N ~-chloreethylammonium s~lts and 2-(4-isopropyl-4-methyl-5-oxo-2-Lmidazolin-2-yl)-3-quinolinecarboxylic acid having growth-regulat.ing properties are ~lso known (EP-A 149 083~.
I~ is an ob~ect of the present in~ention to provide novel effective ~ynergistic mixtures for regula~-ing plant growth.
~e have found that this ob~ect is achieved by ~he synergistic mixtures defined at the outset. Method~ ~or u~ing these mixtures as plant growth regulators were also found.
In view of the intended use in the novel syner-~istic growth-regulating agents, suitable substituents of the c~mpound~ II are the following radicals~
R1 is Cl-C4-alkyl, such as methyl, ethyl, propyl, 1-methyleth~l, butyl/ l-methylpropyl, 2-methylpropyl or dimethylethyl, preferably methyl, ethyl or 1-methyl ethyl, in particular methyl or l-methylethyl;
R~ is Cl-C4-alkyl, such as me~hyl, ethyl, propyl, 1-methylethyl, butyl, l-methylpropyl, ~-methylpropyl o~
1/l-~imethylethyl, preferably methyl or ethyl, in par-ticular meth~1, or C3-C6-cycloal~yl, ~uch a~ cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferably cyclopropyl or cyclopentyl, in particular cyclopropyl;
: R3 iY hydrogen;
C1-C12-alkyl, prefsrably branched or straight-chain Cl-C6-alkyl, such as methyl, ethyl, pxopyl, l-methyllethyl, 3~ butyl, l-mathylpropyl, 2-methylpropyl, 1,1-dLmethyllethyl, pentyl., 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2 dimethylpropyl, l-ethylpropyl~ hexyl, 1,1-dimethylpropyl, 1,2-di~ethylpropyl, 1-m~thylpentyl, 2-mekhylpentyl, 3-methylpentyl, 4~methylpentyl, 1,1-dimethylbutyl, 1,2-dlmethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-d:Lmethylbutyl~ 3,3-dimethylbutyl, l-ethylbu~yl, 2-e~hyl-butyl, l,1,2-trimethylpropyl, 1,2,2-trimekhylpropyl, - 3 - O.~. 0050~41834 1-e~hyl-1-methylpropyl and l~ethyl-2-methylpropyl, in particular br~nched or straight-chain Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methyl propyl, 2-methylpropyl or 1,l~dLmethylethyl;
C~-C12-alkoxy, preferably branched or straight chain C~-C6-alkoxy, such as methoxy, ethoxyl propoxy, 1-methyl-ethoxy; butoxy, l-methylpropoxy, 2-me~hylpropoxy, 1,1-dLmethylethoxy, pentyloxy, 1-methylbutoxy, 2-methyl~
butoxy~ 3-methylbutoxy, 2,2-dLmethylpropoxy, 1-ethylprop-oxy, he~yloxy, l,l-dLmethylpropoxy, 1.,2-dLmethylpropoxy, l-me~hylpentyloxy, 2-methylpentylo~y/ 3-mathylpentyloxy, 4~Nethylpentyloxy, 1,l-dimethylbutoxy, 1~2-dimethyl-butoxy, 1~3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbuto~y, 2-lS ethylbuto~y, 1,1,2-trimethylpropo~y, 1,2,2-trimethyl-propo~y, l-ethyl-1-met~ylpropoxy or 1-ethyl-2-methyl-propoxy/ in particular branched or straight-chain Cl-C4-alkoxy, such as methoxy, etho~y, propoxy, l-methylethoxy, : ~uto~y, l-me~hylpropoxy, ~-methylpropo~y or 1,1-dLmethyl-ethoxy;
Cl-Cl2-alkylamino, in particular C1-C6-alkylamino, such as methylamino, ethylamino, propylamino, l-methylethylamino, butylamino, 1-methylpropy~lamino, 2-methylpropylamino, 1,~ dimethyle~hylamino, pentylamino, 1 methylbutylamino, 2-methylbutylamino~3-methylbutylamino,2,2-dLmethylprop-ylamino, l~ethylpropylamino, hexy~lamino, 1,1-d~nethyl-propylamino, 1,2-dimethylpropyl2mino, l-methylp~antyl-amino, 2-m~thylp~antylamino, 3-methylpentylamino, 4-methylpen~ylhmino, ~ dimethylbutylamino, 1,2-dlm~athyl-butylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutyl-amino, 2,3-dimethyl~u~ylamino, 3,3-dimeth~lbutylamino, 1-ethylbutylamino~ 2 ethylbutylamino; 1,1,2-trimethylprop-yl~nino, 1,2,~-trimethylpropylamino, 1 ethyl-l-methyl-~,, propylamino and 1-ethyl-2-methylpropylamino;
di-C1-C12-alkylamino, in particular di-C~-C~-alkylamino, preferably di-Cl-Cb-alkylamino, ~uch a~ N,N~dimethyl~mino, diethylamino, N,~-dipropyl~mino, ~,N-di-(1-methyl-., ;~
, ., ,, .
- ~ - O.Z. 0050/41~34 ethyl)amino, N,N-dibu~ylamino, N,N-di~(1 methylpropyl)~
amino, N,N-di-~2-methylpropyl)-amino, N,N-di-(1,1-dLmethylethyl)-amino, N-ethyl-N-methylamino, N-methyl-N
propylamino, N-methyl-N-(l-methylethyl)-amino, N-butyl-N-methylamino, N-methyl-N~ methylpropyl)-amino, N-methyl-N-(2-methylpropyl)-amino, N-(1,1-d~nethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(l-methylethyl)~amino, N-butyl-N~ethylamino, N-ethyl-N-(l-methylpropyl)-amino,N ethyl-N-(2-methylpropyl)-amino,N-ethyl-N~ d~nethylethyl)-~mino, N~ methylethyl)-N-propylamino, N-butyl N-propylamino, N-(1-methylpropyl)-N propylamino, N~(2-methylpropyl)- N-propylamino,:N-(l,l-dLmethylethyl)-~-propylamino, N-butyl-N-tl-methylethyl) amino, N~ methylethyl)-N-(1-methylpropyl)-amino, N~
methylethyl)-N (2-methylpropyl)-aminol N-(1,l-dLmethyl-ethyl)-N-Il-methylethyl) amino, N-butyl-N~ methyl-propyl)-amino,N-butyl-N~(2-methylpropyl)-amino,N-butyl-N-(l,l-dimethylethyl)-amino, N~ methylpropyl)-N-(2-methylpropyl)-amino, N-(l,l-dLmethylethyl)-N (1 methyl-propyl)-amine and N-(l,l-dLmethylethyl)-N~(2-methyL-propyl)-amino;
phenyl, phe~o~y or phenylamino, where the aromatic radical3 may carry from one to five halogen atoms, such a~ fluorine, chlorine, bromine or iodine, preferably fluorina, chlorin* or bromine, in particular f1UOI ine or chlorine, and/or from one to threa of the following group~:
Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l~methylpropyl, 2-methylpropyl or 1,l-dimethyleth-yl~ praferably methyl, ethyl or 1-methylethyl, in par-ticular methyl;
Cl-C4-haloalkyl, in particular Cl- or C2 haloalkyl, such a~
chloromethyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifl.uoromethyl, chloro1uoro-methyl, dichloro1uoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2l2-difluoroathyl, 2,2,2-tri~ oroethyl, 2-chloro-2-fluoroethyl, ~ 5 - O.Z. 0050/41834 2-c~loro-2,2-difluoroethyl, 2,2-dichloro~2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl, preferably difluoromethyl or trifluoromethyl, in particular tri-fluoromethyl;
Cl-C4-alkoxy, such as methoxy, ethoxy, propoxy, 1 methyl-ethoxy, butoxy, l-methylpropoxy, ~methylpropoxy or 1,1-dLmethylethoxy, preferably methoxy, ethoxy, 1-methyl-ethoxy or 1,1-dLmethyletho~y, in particular metho.~y or 1-methylethoxy;
Cl-C4-haloalkoxy, in particular Cl- o:r C2-haloalkoxy, ~uch as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluorometho~y, chloro~
fluoromethoxy,dichlorofluoromethoxy,chlorodi1uorometh-oxy, 1 fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroe~hoxy, lS 2,2,2-trifluoroe~ho~y,2-chloro-2-fluoroethoxy,2-chloxo-2,2 difluoroethoxy, 2,2-di~hloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or pentafluoroetho~y, preferably di-fluorometho~y or trifluorome~ho~y;
Cl-C4-alkylthio, such as methylthio~ ethylthio, propyl-~0 thio, l-methylethylthio, butylthio, l-methylprop~lthio, 2-methylpropylthio or l,l--dLmethylethylthio, preferably methylthio, or C1-C4-haloalkylthio, in particular C~ or C2 haloalkyl-thio, ~uch as chloromethylthio, dichlorome~hylthio, txichloromethylthio, fluoromethylthio, difluoromethyl-thio, trif luoromethylthio, chlorofluoromethylthio~
dichlorofluoromethy~thio, chlorodifluoromethylthio, 1-fluoroethylthio, 2 fluoroethyl~hio, ~,2-difluoroethyl-thio, 2,2, 2-trif luoroethylthio, 2-chloro-2-fluoroethyl thio, 2-chloro-~,2-difluoroethyl~hio, 2~2-dich:Loro-2-fluoroethylthio, 2,2,2-trichloroQthylthio or penta-fluoroethylthio, preferably difluoromethylthio;
R4 is hydroyen;
halogen, such as fluorine, chlorine, bromine or iodine, ; 35 pre~erably ~luorine, chlorine or brominet in paxticular ~luorine or chlorine;
Cl-C4-alkyl/ such as methyl, ethyl, propyl, 1-methyle~hyl~
~ ' - 6 - O.Z. 0050/~1834 butyl~ l-methylpropyl, 2-methylpropyl or lrl-dlmethyleth-yl, preferably m~thyl, ethyl or l-methylethyl or 1,1 dimethylethyl;
C1-C4-haloalkyl, in particular Cl~ or C2-haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifluoromethyl, chlorofluoro-methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1~
fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2 difluoroe~hyl, 2,2-dichloro-2-fluoroethyl, 2,2,2 tri-chloroethyl or pent~fluoroethyl, preferably difluorometh-yl or trifluoromethyl, Cl-C4-alkoxy, such as metho~y, ethoxy, propoxy, 1 methyl-ethoxy, buto~y, l-methylpropoxy, 2-methylpropoxy or 1,1-dLme~hyletho~y, preferably metho~y, ethoxyl 1-methyl-ethoxy or 1,1-dLmethyletho~y, in particular methoxy or l,1-dLmethylethoxy;
Cl-C4~haloalkoxy, in particular C~- or C2-haloalkoxy, such as chloromethoxy, dichloromethoxy, tr.ichloromethoxy, ; 20 fluoromethoxy, difluorometho~y, trifluoromethoxy, chloro-fluoromethoxy r dichlorofluorometho~y,chlorodifluorom2th-oxy, 1 fluorosthoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2/2,2-trifluoroe~hoxy,2-chloro~-fluoroethoxy,2-chloro-2,2-difluoroetho~y, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or pentafluoxoethoxy, preferably di-fluoromethoxy or ~rifluorome~hoxy;
Cl-C4-alkylthio, such as methylthio, ethylthio, propyl-thio, l-methylethylthio, butylthio, l-methylpropylthio, 2-methylpropylthio or l,l-dLmethylethylthio, preferably methylthio or ethylthiof or C1-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-thio, such a3 chloromethylthio, dichloromethylthio, tr~chloromethylthio, fluoromethylthio, difluoromethyl-thio, triEluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethyl-thio, 2,2,2~rifluoroethylthio; 2-chloro-2-fluoxoethyl-- 7 - o.Z. 0050/41834 thi~, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroe~hylthio, 2,2,2-trichloroethylthio or pentafluoroethylthio, preferably difluorome~hylthio, and R5 and R6 independnetly of one another are each one of the groups stated in general and in particular for R4 or together form a 1,3-butadi0ne-1,4-diyl group which may carry from one to four halogen atom~3, such as fluorine, chlorine, bromine or iodi~e, preferably fluorina, chlor-ine or bromi~e, in particular fluorine or chlorine, and/or from one to three of the following groups:
Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methylpropyl, 2-meth~lpropyl or l,l-dLmethyleth-yl, preferably methyl, ethyl or l-msthylethyl;
Cl C4-ha}oalkyl, in particular Cl- or C2-haloall~yl,~3uch as chloromethyl, dichloromethyl, trichloromethyl, fluoro~
methyl, difluoromethyl, trifluoromethyl, chlorofluoro-methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2~2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-~-fluoroethyl, 2-chloro~2,2-difluoroethyl, 2,2-dichloro-2-flu~roethyl, 2,2,2-tri-chloroethyl or pentafluoroethyl, preferably ~i~luorometh-yl or trifluoromethyl;
Cl-C4--alkoxy, ~uch a~ methoxy, etho~y, propoxy, l-methyl-ethoxy, butoxy, 1-methylpropoxy, 2-methylpropo~y or 1,1-dLmethylethoxy, preferably methoxy, ethoxy, l-methyl-athoxy or l,l-dLmethylethoxy;
C1-C4-haloalko~y, in particular Cl- or C2-haloalkoxy, such : as chloromethoxy, dichloromethoxy, trlchloromathoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro-fluoromethoxy,dichlorofluoromethoxy,chlorodifluorometh-oxy, 1-fluoxoethoxy, 2-~luoroethoxy, 2,2-difluoroethoxy, 2,2,2 trifluoroetho~y,2-chloro-2-fluoroethoxy,2~chloro~
2,2-difluoroethoxy, 2,2-dichloro-2-~luoroethoxy, 2,2,2-trichloroethoxy or pentafluoroethoxy, pref~rably di-fluoromethoxy or trifluoromethoxy;
C1-C4-alkyl~hio, ~uch a~ methylthio, et.hylthio, propyl-thio, l-methylethylthio, butylthio, l-methylpropylthlo, , , , - 8 - O.Z. 0050/4183~
2-methylpropylthio or 1,1-d~nethylethylthio, preferably methylthio or Pthylthio, or Cl-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-thio, such as chloromethylthio, dichloromethylthio, trichloromethylth.io, fluoromethylthio, difluoromethyl-thio, trifluoromethylthio, chloro~luoromethyl~hio, dichlorofluoromethylthio, chlorodifluoromethylthio, l-fluoroethylthio, 2-fluoroethylthio/ 2,2-difluoroethyl-thio, 2,~,2-trifluoroethylthio~ 2-chloro-2-fluoroethyl thio, 2-chloro-2,2-difluoroethylthio, 2,2 dichloro-2-fluoroethylthio, 2,2,2-trichloro~thylthio or penta-fluoroethylthio, preferably difluoromethylthio.
In view of the intended use in the synergis~ic agents, particularly preferred compounds II are those in which ~he substituents have the following meanings-R1 is C1 C~-alkyl as stated above, in particular methyl;
R2 is Cl-C4-alkyl as sta~ed above, in particular methyl or 1 methylethyl, or C3-C6-cycloalkyl as stated above, in particular cyclo-propyl;R3 i~ hydrogen; hydxoxyl;
Cl-C8-alkyl a~ stated abo~e, in particular branched or straight-chai~ Cl-C6-alkyl a~ stated above;
Cl-Ca-alkoxy a~ ~tated above, in particular branched or straigh~-chain Cl C~-alkoxy a~ s~ated above;
C1-C~-alkylamino as stated above, in particular Cl-C6-alkylamino a~ ~tated above;
di-Cl-C8 alkyl~nino as stated a~ove, in particular di-Cl-C4-alkylamino as stated a~ove;
phenyl, phsnoxy or phenylamino, where the aromatic radicals may carry from one to ~ive halogan atoms as stated above, ln particular fluorine or chlorine, and/or from one to thres of the following groups:
Cl-C4-alkyl as stated above~ in particular methyl;
C1-C~,-haloalkyl as sta~ed above, in particular difluoro-methyl or ~rifluoromethyl;
C1-C4-alko~y as ~tated above~ in particular methoxy .
.' .
.
. ~ ; . ,.
g ~ O.Z. 0050/~1834 ethoxy, 1-methylethoxy or l,1-dLmethylethoxy, Cl C4-haloalkoxy as stated above, in particular difluoromethoxy or trifluoromethoxy;
Cl C4-alkylthio as stated above, in particular methylthio or ethyl~hio, and C~-C4-haloalkylthio as stated above, in particular difluoromekhylthio;
R4 is hydrogen;
halogen as stated above~ in particular fluorine or chlorine;
Cl-C4-al3~yl as ~tated above, in particular methyl or 1,1-dLmethylethyl, Cl-C4-haloalXyl as stated above, in particular difluoro-- methyl or trifluoromethyl;
C1-C4-alkoxy as stated above, in particular methoxy or l,l-dimethylethoxy;
C~-C4-haloalkoxy a~ ~tated above, in particular difluoro-; methoxy or trifluoromethoxy;
C~-C4-al~ylthio as ~tatad above, in particular methylthio or ethylthio, or C1-C4-haloalkylthio as stated above, in particular di~luoromethylthio, and R5 and R~ indepedently of one another are each one of ~ha groups ~tated in general and in particular for R4 or togethar fonm a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atom~ as stated above, in ~rticular fluorine or chlorine, and/or from one to three of the following groups:
C~-C~-alkyl a~ stated above, in pa.rticular meth~l;
C'1~C4-haloalkyl as ~tated above, in particular trifluoro-methyl;
Cl-C4-~al3coxy a~ s~ated above, in particular methoxy;
Cl-C4-haloalkoxy a~ stated above, in particular difluoro-methoxy or trifluorome~ho~y;
C1-C4-al3~ylthio as ~tated above, in paxkicular met.hylthio, and C~-C4-haloalkylthio as stated above, in particular difluoromethylkhio.
- 10 - O.Z. 0050/41~34 Particularly preferred synergistic agen s for regulating plant growth are those which contain an N,N-d ~ ethylpiperidinium salt or an N,N,N trimethyl-N 2-chloroethylammonium salt as the growth-regulating quater-nary ammonium salt.
Particularly prefarred ~nergistic agents of thi~
type are ~hose which contain, in addition ~o the N,N-dime~hylpiperidinium salt~ or N,N;N-trimethyl-N 2-chloro~
ethylammonium salts, an Lmidazolinyl derivative of the general formula II, where R1 is C1-C4-alkyl as stated ahove, in particular methyl;
R2 i~ C1-C4-al ~ 1 as stated above, in particular methyl or l-methylethyl, or C3-C6-cycloal ~ 1 a stated above, in particular cyclo-p~pyl;
R3 is hydrogen; hydroxyl;
Cl-C~-alkyl as stated above, in particular branched or straight-chain C1-C:~-alkyl a~ stated above;
C1 Ct~-alkoxy as stated above, in pa.rticular branched or 2 0 straight-chain C1-C6-alkoxy as st~te~ abo~e, C1-CB-a~ nO a~ stated above, in particular C1-C6-alkylamino as stated above;
di-Cl-Ca-alkylamino a~ stated above, in particular di-C1-C4-alkylami~o as ~tatsd above~ or phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms as ~tated above r in particular f luorine or chlc~rine, _., and/or from one to three of the following groups:
C1-C4-alkyl a~ ~tated above, in particular methyl, Cl-C4-haloalkyl a~ stated above, in particular difluoro-methyl or trifluorome~hyl;
Cl~C4-alko~y a~ statad above, in particular metho~y or ethox~;
C1-C~-haloalko~y a~ stated above, in particular difluoro-methoxy or ~rifluorometho~y;
C1-C4-alkylthio a stated above, in paxticular methylthio or ethylthio, ?
~ O.Z. 0050/41~34 and C,-C4-haloalkylthio as stated above, in particular difluoromethylthio;
R4 is hydrogen or halogen as stated above, in particular fluorine or chlorine, and Rs and R6 independently of one another are each hydrogen;
halogen as stated above, in part:icular ~luorine or chlorine;
Cl-C4-alkyl as stated above, in particular methyl;
Cl-C4 haloal~yl a ~tated above, in particular trifluoro-methyl;
Cl C4 alkoxy a3 stated above, in particular methoxy or I t l-dimethyletho~y;
Cl-C4-haloalkoxy as stated above, in particular difluoro-methoxy or trifluoromethoxy;
Cl-C~-alkylthio a~ ~tated abo~e, in particular methylthiot :~ or Cl-C4-haloalkylthio as stated above, in particular difluoromethyl~hio, or tog0~her form a 1,3-butadiene-1,4-diyl gxoup which may carry from on~ to four halogen atoms as stated above, in : particular fluorine or chlorine, and/or one of the following groups.
Cl-C4 alkyl a~ st ted above, in particular methyl;
: 25 Cl~C4-haloalkyl a~ ~ated above, in particular trifluoro-methyl;
Cl-C4-alkoxy as stated abo~e, in particular methoxy;
C1-C4-haloalkoxy as ~tated above, in particular difluoxo methoxy or trifluorometho~y;
Cl~C4-alkylthio as stated above, in particular methylthio, or Cl-C4~haloalkylthi.o as stated above, in particulax difluoromethylthio.
~'he active ingredients can be applied together or separately, at the ~ame time or in succession~ before, ; 35 duxing or after ~mergence o~ the plan-ts.
In the syner~istic agent~, the weight ratio of ~mmonium salt I to imidazoli.ne derivative II is from - 12 - O.Z. 0050/41834 0.1 . l to 1000 : 1, preferably from 1 : 1 to 950 , 1, in particular from 1.5 : 1 to 920 : 1.
The novel agents can be used, for example, in ~he form of directly sprayable solutions, powders, suspen-sions, including concentra~ed Aqueous, oily or other suspensions or dispersions, emulsions, oil dispersion~, pastes~ dusting agents, broadcasting agents or granules, by spraying, atomi ing~ dusting, broadcasting or pouring.
The application forms depend on the intended uses. Th~y should in any case ensure a very fine distribution of the novel active ingredien~s.
The compounds I and II axe suitable in general for the preparation of directly sprayable solution~, emulsions, pastes or oil dispersions. Suitable inert additive~ are mineral oil fractions ha~ing a medium ~o high boiling point, such a~ kero~ene or diesel oil, and coal tar oil~ and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbon~, eg. toluene, xylene, paraf~inr tetrahydronaphthalene, alkylated naph~halenes or derivative3 thereof~ methanol, ethanol, propanol, butanol/ cyclohexanol, cyclohexanone, chloro-benzene, i~ophorone or strongly polar solvents, such as ~,N-dimethylformamide, dimethyl sulfoxide, N-methyl-pyrrolidone or water.
Aqueous application forms can be prepared from emulsion concenkra~, dispersion~, pastes, wettable powders or water-disper~ible granules by adding water.
For the preparation o emulsion~ t paste~ or oil dispar-sion~, the ~ubstrates, a~ such or dissolved in an oil or sol~ent, can be homogenized in water by means o wekting agent~, adherents, disper~ant~ or emul~ifier~. Howev9r, it i3 also possible to prepare concentrates which con~ist o~ activ~ ~ubstance, wetting agent~, adherents, di~per-san-t~ or emulsl~ier~ and possibly 301~ent or oil and which are suitable for dilution with water.
Suitable surfactant~ are the alkali metal, alkaline earth metal and ammonium salts o~ aromatic - 13 - O.Z. 0050/41834 sulfonic acids, for example lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkylsulfonate~ and alkylarylsulfonates, alkylsulfate~, lauryl ether sulfates and fatty alcohol sulfates, and ~alts of sulfated hexa-, hepta- and octa-decanols, and of fatty alcohol glycol ethers, condensate~
of sulfonated naphthalene and its derivatives with formaldehyde~ condensates of naphthalene or of naph-thalenesulfonic acids with phenol and formaldehyde~
polyoxyethylene oc~ylphenol ethers, ethoxylated isooctyl,- octyl- or nonylphenol~ alkylphenol polyglycol ether~, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated cas~or oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, ligninsulfite waste liquors or methylcellulose.
Powders, broadcasting agents and dusting agents can be prepared by mixing or milling the active sub-stances together with a solid carrier.
Granules, for example coa~ed, Lmpregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earth~, such as silica gel, silicas, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, kie~elguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea3, and vegetable products, such as grain flours, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carrier~.
~he formulations contain from 0.1 to 95, prefer-ably from 0.5 to 90, % by weight of the active in-gredients. The active ingredients are used in a purity of from 90 to lO0~, preferably from 95 to 100% (according to the NMR spectrum).
~he growth regulators or the active ingredients O . Z . 0050/41834 can be applied by the preemergence or postemergence method. If the active ingredients are less well tolerated by certain crops, it i~ pos~ible to use application methods in which the herb.icides are sprayed 5 with the aid of sprayers in such a way that as far as poss.ible they do not come into contact with the leaves of the sensitive crops while the active ingredients reach the leaves of undesirable plant~ g:rowing underneath or the uncovered soil surface ~post-directed, lay by).
The application rates of active ingredient mixture are from 0.01 ~ 0.01 to 2 ~ 0.001, preferably front 0 . 03 + O . 02 to 1 + O . 001, kq/ha of active substance (a.s.), depending on the s~a~on, target plants and stage of grow~h.
The synergistic mixtures can influence virtually all ~tage3 of development of a plant in di~ferent ways and are therefoxe used a~ growth regulators. The range of activity of the plant growth regulators depend~ in particular a) c7}1 the plant ~pecies and variety, b) on the time of application~ ba~ed on the stage of development o~ tha plant, and on the ~ea~on, r) on the place and method of application (for example s~ed dre~ing, ~oil treatment, foliage application or trunk in~ection in .he case of trees), d) on climatic ~actors, eg. temperature, amount of _ precipitation and also length of day and light inten~ity, e) on the soil quality ~including fertilizer applica-tion), f) on the formulation or application form of the active ingredient and finally g) on the ~oncen~rations in which ~he active substance is used.
From ~he various possibl.a applications of the novel agents in cultivation, in agriculture and in hortictllture, ~ome are mentioned below.
- 15 - o.Z. 0050/~1834 A. The vegetative growth of the plant~ can be greatly inhibited with the compounds which can be used according to the invention, this being manifested in paxkicular in a reduction in the growth in length. The treated plants accordingly h ve a stunked growth; more-ov~r, a darker leaf coloration is ob~erved.
Reduce~ intensity of growth of yrasses along road edges, hedges and canal banks and on lawn area~, such as parks, sports grounds, orchards, ornamenkal lawn~ and airfield~, proves advantageous in practice, enabling the labor-inten~ive and expensive cutting of lawns to be rsduced.
The increase in the strength of crop~ su~c~ptible to lodging, such a~ cereals, corn, sunflowers and soy-bean, is also of economic interest. The re~;ultingshortening and strengthening of the stem reduce or slLminate the danger of lodging (of bending) of plants - under unfavorable weather conditions prior to harvesting.
The u~e of growth regulator~ for inhibiting the growkh in length and for changing $he tLme of ripening of ootton iB also importan~. This permit~ completely mechanized harvesting of thi~ important crop.
In the ca3a of fruit tree~ and other trees, the growth r~gulators permit a reduction in cutting cost~.
~oreover, the alternance of fruit trees can be broken by growth ragulators.
The lateral branching of the plants can also be increased or inhibited by the u~e of grow~h regulators.
Thi~ is of interest if, for example, in the case of tobacco plants, it i~ intended to inhibit the formation of ~ide ~hoot~ in favor of leaf growth.
The ~rost rasi~tanco can also be considerably lncrea ed with growth regulator3, for example in wintar rape. On the one hand, the growth in length and the development of a leaf or plant mas~ which i3 too luxuri-ant (and hence particularly su~ceptible to fro3t) are inhibited. On the other hand, the young rape plants are 16 - O.Z. OOS0/41834 held back in the vegetative stage of development after sowing and before the onset of the winter frosts~ in spite of favorable growth conditionst This also elLmina tes the danger of fro~t to plants which tend to ~xhibit a premature decline in ~he inhibition of blooming and to go over into the genPrative phase. In other crops too, for sxamplP winter cereals, it is advantageous if the stocks are well tillered in the fall as a result of treatment ~ith novel compounds bul: do no~ en~er thP
winter with too luxllriant a growt.h. This makes it possible to avoid high sensitiYity to frost and, owing to the relatively small leaf or plant mass, attack by various diseasP~ ~ fox example fungal disease). Inhibi tion of the vegetative growth furthermore permits denser planting of the soil in the case of many cxop~, making it possible to achieve a greater yiel , ba~ed on soi:L area.
. The growth regulators make it possible to achieve greater yield both of plant part~ and of plant in-gredient~. For example, it i~ po ~ible to induce the grow~h of laxger amounts o bud~, blooms, leaYes, fruits, seeds, roots and tuber~, to increase the content of sugar in sugar beet~, sugar cane and citru~ fruits, to increase . the protein content of cereal~ or soybean or to stLmulate greater lat~x flux in rubbsr tree~.
By intervening in the plant metaboli~m or by prcmoting or inhibiting vegetative and/or generative growth, -the synergistic agents can result in increased yield~, C. Finally, both shortening or lengthening of the 8taga9 of development and acceleration or re~ardation o~
the ripening of the haxvested plant parts bsfore or after harve~ing can be achLeved with plant growth regula~or~.
For example, it is of economic interest to facilita~e harve~ting, thi~ being pe~litted by con-centrated dropping or reduction in ~the adhesion to the tree in the ca~e of citrus fruit~, olive~ or other specie~ and varieties ~f pomes, drupes and hardshall ;
- 17 ~ O.Z. 0050/~1834 fruit. The same m~chanism, ie. promotion of the forma-tion of absci~sion tissue between the fruit or leaf part and the sprout part of the plant is also essential for readily controllable defoliation of crops such as for example cotton.
D. Furthermore, the water consumption of plants c~n be reduced with growth regulators. This is particularly important for agricultural areas which have to be artifi-cially irrigated at great expense, for example in arid or semiarid regions. By using the novel ~ubstances, it is po~sible to reduce the intensity of irriga~ion and hence to carry out more economical farming. Under the influ-ence of growth regulators, the available water is bet~er utilized becau~e, in~er alia, 15 - ~he extent of opening of the stomata is re~uced, - a thicker epidermi~ and cuticula are formed, - root penetration o~ the soil i~ improved and - the microclLmate in the crop is advantageou~ly affected by more compacted growth.
The novel synergis~ic agents c~n be fed to the crops both via the seed ~as seed dre~sings) and via the soil, ie. through the root and, particularly preferably, via the foliage by spraying.
Because of the good toleration by plants, the application rate can ba greatly varied.
In view of the wide range of applica~ion methods, the novel agents can be used in cere 1 crops and cotton.
The synergi~tic effect can be determined by the formula of S.R. Colby (Wa~ds 15 (1967), 20~2) E = X ~ Y - X Y / 100 where the variables have th~ following meanings:
X 18 the ~ea~urable effect of the active ingredient I at an applica~ion .ra~e ~a], ; Y is the mea8urable efEect of the active ingredient II at an appl~cation rate ~b] and is the expected measurable efect of a mixture of active ingredient I at the application rate ~a] and of j;, , ! , ~;, . ..
- 18 ~- O.Z. 0050/41834 active ingredient II at the application rate ~b].
From the difference between the expected v~lue ~
according to Colby and the measured value, it is possible ~o determine whether there is a synergistic efect (reinforcement of the effect ox increase of activity) or an antagonistic effect (weakening of the effect or reduction in activity), or if there are merely additive effec~s on the activity, this being the case if the two values correspond.
The Lmproved biological action of the mixtures compared with the individual substances in cereal crops and cotton can be demonstrated in field trials.
Various mix~ures of th~ following compouncls were inves~igat~d:
A
N~N,N~Trimethyl-N-~-chloroethylammoniumchloride(chloro-mequat chloride) N,N-DLmethylpiperidinium chloride ~mepiquat chloride) C
2-~4-Isopropyl-4-methyl-5-oxo-2-imidazolin 2-yl)-3-quinolinecarbo~ylic acid (imazaquin) D
I~opropylammonium 2-(4-isopropyl-4-methyl-S-oxo-2-imidazolin-2~yl)~3-nicotinecarboxylate (imaæapyr) : E
5-Ethyl 2-(4-isopropyl-4-methyl 5-oxo-2-imidazolin 2 yl)-3 nicotinecarbo~ylic acid (imazethapyr) ~he trial~ were carried out on plots, each measuring 12.5 m2 (cereals) or 50 m2 (cotton), with 4 replicates in each ca~e. Cultivation, ~ertilizer ap-plication and the use of crop protection agent~ again~t growth of weeds and attack by fungi and by in~ect pes~s were carried out in a manner conventional ~or t~le location.
The novel agent~ were applied by the post-emergence method (3.5 bar, 400 l/ha of water).
~ '` l"`1 r r - 19 - - Z ~ 0(~50/41~33 The ~bovemPntioned cexeal trial~ show that the novel mixtures are clearly superior to the known mixture A ~ C (EP-A-149 083). Furthenmore, Ta~le 2 shows that a mixture consisting of two diferent quaternary ammonium compounds with a triazole has an action superior to that of ~he known combination of A + C.
TABL~ 1 Crop: Winter barley (variety: Marinka) Type of soil: Clayey loam Sowing: Saptember 28, 1988 Treatment: March 28, 1989 Evaluation: Plant damage Nay 12, 1989 Height of growth May 17, 1989 Sub~tance g/ha of Plant Height of grow~h active damage cmDif~erence rom ingredient % control ~ (cm)_ Control - 0 102.1 A 690 0 101.60.5 D 10 5 72.5- 29.6 A + D 6gO ~ 5 6 71.9 - 30.2 A + D 690 ~ 10 6 57 4 6 - 44.5 A + D 690 ~ 20 11 41.4- 60.7 A ~ C 759 ~ 16.5 3 84.0- 18.1 ~ ~ C 1150 + 25 10 78.9- 23.2 - 20 - OOZ~ 0050/4183 Crop: Winter wheat (variety Baroudeur) Type of soil: Clayey sand Sowing: October 2, 1989 Txeatm~nt: March 28, 1990 Evaluation: Plant damage May 17, 1990 Height of growth June 5 t 1990 Substance g/ha of Plant Height of growth active damage cm Difference from ingredient % control ~ . (cm) Control 0 0 108.0 A + E 920 + 1 0 100.8 - 7.2 A + E 920 t 2 0 99O2 - 8.8 A + E 920 ~ 4 0 99.8 - 8.2 ?
A ~ B ~ E 690 + 230 ~ 20 100.5 - 7.5 A + C 920 + 2 0 101.0 7.0 T~BLE 3 Crop: Winter wheat (varietyO ~axoudeur) ~ype of ~oil: Sandy loam Sowing: October 12, 1989 Treatment: March 5, 1990 Evaluation: Plant da~age June 6, 1990 : Internodal length Ju~e 6, 1990 Ear length June 6, 1990 Substance g/ha o Plant Internodal length Ear length active damage cm Dif~erence cm Difference ingredient ~ fxom con~rol From control cm cm ~
Control 0 a 5.2 8.4 A ~ C 920 -~ 2 0 3.B - 1.4 8.3 ~.l A -~ E 920 ~ 2 0 3.5 - 1.7 8.5 +0,1 . . :
:., -. , , ~ . '' :` :
- 21 - O.Z. 0050/41834 Crop: Winter wheat (variety: Baroudeur3 Type of soil: Sandy loam Sowing: October ~, 1989 Treatments March 1, 1990 Evaluatîons Plant damage May 10, 1990 Height of yrowth May 10, 1990 Substance g/ha of Plant Height of growth active damage cm Difference from 13 ingredient ~ con~rol ~cm) Control 0 0 96.7 A ~ C 920 + 2 0 ~7.6 ~ 9.1 : 15 A + E 920 ~ 1 0 86O2 ~ 10.5 A + E 920 ~ 4 0 86.9 - 9.8 _ , - 22 - O. 2 . 0050/4183 Crop . Winter wheat ( vari ty: Rraka Type of soil: Loamy sand Sowing : November 7, 1 9 8 9 Treatment: April 2, 1990 ~valuation: Plant damage June 6, 1990 Height of growth June 6, 1990 Substance g/ha of Plant Height of growth active damage cm Diffç?rence from ingredien~ % control ( cm Control 0 0 117 . 0 B 690 0 107 . 0 - 10 . 0 1~ C 5 0 11~.5 ~ 1.5 B ~ C 690 + 2 . 5 0 lG6 .1 -10 . 9 A + C 690 ~ 15 0 106 . 9 - 10 .1 EXANPI.ES 6 AND 7 The ~ynergistic e~fect of ~he mixture A + D is demon~trated using barley. It is noted that the addition oiE > 10 g/ha of active ingredient o~ ~ubstance D can lead to plant damage.
.
' ' , - 23 - O.Z. 0050/41834 Crop: Su~mer barley (variety: Gimpel) Type of ~oil: Clay Sowing: March 20, 1989 Treatment: May 18, 1989 Evaluation: Plant damage June 2, 1989 Height of growth Juns 12~ 1989 Substance g/ha of Plant Height of growth active damage cm Difference from ingredient % control ~cm) Control 0 0 101.2 A 690 0 9fi.9 ~ 4,3 D 10 5 55.6 - 45.6 A ~ D 6~0 ~ 5 7 44.6 ~ 56.6 A ~ D690 ^~ 10 8 42.9 - 58.3 A + D690 t 20 8 42.5 - 58.7 TABL~ 7 : 20 Crops Winter barley (variety: Igri) Type of soil: Very clayey loam Sowingo September 22, 1988 Trea~ment: Rpril 21, 1990 Evalllation: Plant dama~e May 15, 1989 : 25 Height of g~owth MAY 22, 1989 Substance g/ha of Plant Height of growth _ active damage cm Difference from ingredien~ % control (cm) .... ~
Control 0 0 111O2 ~90 0 111.2 0 D 10 12 82.0 - 29.2 A + D 690 ~ 10 21 71.2 - 40.0 A ~ D 690 -~ 20 54 63.8 - 47.4 _ ~4 ~ 0.2. 0050/41~34 ~XAMPLES 8 TO 10 In the case of wheat and barley, the mixture A -~
E also leads to synergistic shortening of the stem, im-proved strength and correspondingly greater yields.
Crop: Summer wheat (variety: Ralle) T~pe of soil: Clay Sowing: March 20, 1989 Tre~tmen~. May 18, 1989 Evaluation: Plan~ damage June ~, 1989 Height of growth June 130 1989 Substance g/ha of Plant Height of growth active damage cm Differ~:nce from ingredient ~ control (cm) Control 0 0 7g.8 A 690 0 63.0 - 16.8 E 10 0 7~.8 - 1.0 A + E 690 ~ 5 0 50~1 - 19.7 A + E69~ ~ 10 0 57.8 - 22.0 E690 + 20 4 56.0 - 23.8 TABL~ 9 Crop: Summer wheat (variety$ Ralle) Type of soil: Loam~ ~and Sowing~ February 21, 1989 Tre~ment: ~ay 12, 1989 Evaluation: Plant damage Jun~ 21, 1989 Height of growth Augu~t 3, 1989 Substanca g/ha of Plant Height o~ gxowth active damage cm Differerlce from ingred.ient % control ~cm) Control0 0 36.2 6~ 0 36.8 ~ 0.~
E 10 0 3~.5 - 1.7 '' ' .
.
- 25 - O.Z. 0050/41834 A + E 690 ~ 10 0 39O1 + 2.9 Crop: Winter barley (varietyo Igri~
Type of soil: Very clayey loam Sowing: September 22, 1989 Treatment/ April 21, 1989 Evaluation: Plant damage May 15, 1989 Lodging July 5, 1989 Grain yield 3uly 11, 198g 10 Substance g/ha of Plant Lodging/ Grai~ yield/
active damage difference ~iff~rence ingreclient from control frc~ con~l % ~%] [%]
. . .
Control0 0 46 75.5 690 0 48 + 2 69.7 5.8 0 ~ + ~ 69.3 - 6.2 A + E690 + 10 0 34- 12 76.9 ~ 1.4 A + E690 + 20 0 3610 76.2 ~ 0.7 Mixkures consisting of compounds B + C lead to a synergistic inhibition of growth in barley, whsat and cotton. The resulting improved strength is illu~trated by Exampl~ 13.
- 26 - 0.~. OGSO/41834 TABLE ll Crop: Summer wheat (variety Ralle) Type of ~oil: Clay Sowing: March 20, 1989 Treatment: May 19, 1989 Evaluation: Plant damage June 22, 1989 Height of growth June 13, 1989 Substance g/ha ofPlant Height of growth activedamage cm Difference from ingredient ~ co~trol (cm) .. _ . . ~
ControlO 0 80.6 B 690 0 66.0 ~ 14.6 C 10 0 ~l.O + 0.4 : ~ ~ C690 + lO O 61.5 - 19.1 B + C690 + 20 7 49~8 - 30.8 ~ABL~ 12 Crops Winter wheat (variety: Kraka) Type of soil: Loamy sand Sowing: November 7, 1989 Tr~atment: April 30, 1990 . Evaluation- PLant damage June 5, 1990 Heigh~ of growth June 5, 1990 Substance g~ha ofPlant Haight of growth active damage cm Diff~rence from _ ingredient ~ control (cm) Control O 0 9S.1 B 690 0 86.0 - 9.}
C 5 0 95.4 ~ 0.3 B + C 690 ~ 1.25 0 80.3 - 14.8 B + C 6gO ~ 2.5 0 84.0 - 11.1 B + C 690 + 5.0 0 84.5 - 10.6 ,, .
- 27 - O.Z. 005~/41834 Crop: Summer barley ( varie-ty O Gimpel ) Type of soil: Clay Sowing O Marc h 2 0, 1 9 8 9 Treatment: May 18, 19 8 9 Evalua~ion: Plant damage June 2, 198 Height of growth :rune 12, 198 Lodging July 2 4, 19 8 9 Sub~tance g/ha of Pla.nt Height o:E Lodging~
active damage growth~ dif ference ingredient ~ difference from control from control [cm]
[cm]
Control 0 0 95 . 4 38 B 690 0 94 . 4 -1 G 0 4g + 11 C 10 0 91 O 0 -4 . 4 ~0 ~ 2 B + C 690 + 5 0 82 . 2 -13 . 2 0 - 38 B ~ C 690 + 10 14 61. 6 -33 . 8 0 - 38 B + C 690 ~ ~0 14 S4 ~ 8 -40 . 6 0 - 38 Crop: Cotton (variety: SJ - 2 ) Type o~ soll s Sandy loa~
Sowing: ~ebruary 24, 1989 25 Treatmen$ - June 2~, 198g Evaluations Plant damagl3 July 6, 1989 Heiçrht of growth October 5, 1989 Sub~tance ~/ha of Plant Height of growkh active damage cm Difference from ingredient ~ control ~cm]
Control 0 0 125 . 0 B 30 0 116 . 2 -8 . 8 C 10 0 12~.2 ~1.2 B+ C 30 ~ 5 0 ill . 2 -13 . 8 B~ C 30 ~10 0 110 . 5 -14 . 5 13+ (~ 30 ~~0 0 107 . 5 -17 . 5 ,.i j .,,, ,1,.
- 28 - O.Z. 0050/~1834 CropO Cotton (variety- Stoneville sa5 ) Type of soil: Sandy loam Sowing: May 26, 1989 Treatment: July 24, 1989 Evaluation: Plant damage July 31, 1989 Substance g~ha of Plant Height of growth active damage cm Differ~nce from ingredient % control [cm]
Control 0 0 121.2 B 60 0 111.0 - 10.2 ~ 10 0 122.8 + 1.6 B ~ C 60 + 5 0 112.5 - 8.7 B ~ C 6Q + 10 0 lOg.8 - 11.4 B ~ C 60 + 20 0 107~5 - 13.7 Mixture~ o substances B + ~ also lead to a æmaller plant height and grea~er yield~ in the case of barley, wheat and cotton.
~ Crop: Summer wheat (variety: Ralle) .~ Type of soil 5 Loamy sand Sowing: Augus~ 15, 1989 Z5 ~reatment: August 15, 1989 Evaluations Plant damage June 2, 1989 ~Ieight of growth A~gust 3, 1989 Sub~tance g/ha of Plant Hsiyht of growth active dama~e cm Dif~erence from ingredient % control [cm]
Control 0 0 38.0 B 690 0 40.5 -~ 2.5 D 10 0 38.4 + 0.4 B -~ D690 + 5 0 44.6 + 6.6 B -~ D690 -~ ln 0 40.1 + 2.1 B + D690 t 20 5 31.0 - 7.0 I `' ` ~ "' . ' ! .
- 29 - O.Z. 0050/41834 Crop: Summer barley (~ariety: GLmpel) ~ype of soil: Clay Sowing: March 20, 1989 Treatment May 18, 19 8 9 Evaluation: Plant damag~ June 2, 1989 Heigh~ of grow~h June 12, 1989 Substance g/ha of Plant Height of growth active dam~ge cmDifference from ingredient % control ~cm]
Control 0 0 g5.4 B 690 0 94.4 - 1.0 D 10 5 51.8 - 43.6 B + D 690 -~ 10 0 43.9 - 51.5 B + D 690 + 20 6 43.5 51.9 TABL~ 18 Crop: Cotton (variety~ ~C - 510) Type of soil: Loam Sowing^ ~ebruary 28, 1989 Treatment: June 27, 1989 Evaluation: Plant damage July 6, 1989 Height of growth July 26, 1989 Substance g/ha of Plant Height o~ grow~h ac~ivQ damage cmDifference from ingredient % control [cm]
Control 0 0 g6.6 B 30 0 88.7 - 7.g D 10 6 96.6 0 B ~ D 30 ~ 5 3 a4 . 1- 12 ~ 5 B ~ D 30 ~ 10 6 83.4 - 13.2 B -~ D 30 ~ 20 8 80.8 - 15.8 EXAML~LES 19 TO 25 In tha ca~e of baxlsy, oat~, wheat and cotton, it wa~ al~o possible to reduce the height of growth, reduca lodging and increa3e the yield by mixturQs of substances :~ Y'1 - 30 - O.Z. 0050/41834 B ~ E.
TABLE lg Crop~ Summer wheat (variety: Ralle) Type of soil: Clay Sowing: March 20, 1989 Treatment: May 19, 1989 Evaluation: Plant damage June 2, 1989 Height of growth June 13, 1989 Sub~tance g/ha of Plant Height of grow*h active damage cmDiffer~nce from ingredient % control [cm]
Contxol 0 0 80.6 B 690 0 66.0- 14.5 E 10 a 8~oO+ 1.4 B ~ E690 ~ 5 9 60.0- 20.6 ; B + E690 * 10 0 57.023.6 690 + ~0 5 54.0~ 26.6 TA~LE 20 -~ 20 Crop: Winter wheat ~variQtys Xanzler) ~ype of soil: Clay Sowing: ~ctober 4, 1989 : Treatment: April 5, 1990 E~aluation: Plant damage June 5, 1990 Height of growth June 5; 1990 Sub~tanc~ g/ha of Plant Haight of gr~wt;h active damage cm Di~ference frvm inyredient % control [cm]
Control 0 0 122.9 B 690 0 117.2 - 5.7 E 5 0 122.8 - 0.1 B + ~ 690 + 1.25 0 113.2 - 9.7 B + ~ 690 t 2.5 0 114.8 ~ 8.1 B ~ 90 t 5 0 113.4 - 9.5 , - '' ~ ' :
~ ~ .
- 31 - O.Z. 005~/4183 Crop: Winter wheat (variety: Kraka) Type of soil: Loamy sand 50wing: November 7, 1989 Treatment: May 2, 1990 Evaluation: Plant damage June 5, 1990 Height of growth June 5, 1990 Substa~ce g/ha o~ Plant Height of grow*h active damage cm Difference fro~
lD ingredient % con~rol ~cm]
Control a 0 97.9 B 690 0 88.7 - 9.2 E 5 0 ~9.1 ~ 1.2 B ~ E 690 ~ 2.5 0 86.0 - 11,.9 B ~ E 690 -t 5 0 85.4 12.5 TAB~E 22 Crop: Oats (variety. Fl~mingsnova) Type of soil: Sandy lo~m Sowing. March R, 1990 Trea~ment: May 131 1990 : Evaluation: Plant damage June 8, 1990 . Height of growth June 8~ 1990 ; Sub~tance g/ha of Plant Height of growth active damage cm DifferQnce from ingredient % control [cm]
Control0 0 97.5 B 690 0 91.9 - 5.6 E 5 0 95.8 ~ 1.7 B + E690 + 5 0 89.1 - 8.4 - 32 - O. Z . 0050/41834 Crop: Summer barley ( variety: Gimpel ) I~ype of soil: Clay Sowing: March 20~ 1989 Treatment: May 18, 19 8 9 Evall~ation~ Plant damage June 2, 1989 Height of growth June 12, 1989 Lodging J uly 2 4, 1 9 8 9 Substance g/ha of Plant Height of Lodging/
active damage growt:h/ dif feren~e ingredient % difference from con f rom control trol [ % ]
[cm]
Control 0 0 95 . 4 38 B 690 0 94 . 4 - 1. 0 49 ~ 11 E 10 0 93.1 - 2.3 42 +4 E~ ~ E 690 ~ 10 0 91. 6 -3 . 8 36 - 2 B ~ E ~9û ~ 20 6 67 . 5 -27 . 9 0 - 38 2 û TAB~l~ 2 4 Crop s Cottoll ( variety: S~ - 2 ) Type of ~oil: Sandy loam Sowing : Fe~ruary 2 4, 1 9 8 9 I'reatment o June 2 7, 19 8 9 . ~ 25 Evaluation: Plant dsmage July 6, 198~
HQight of growth October 5, 1989 Sub~tance g/ha of Plant Height of grow~h ac:tive damage cm Di~erence from ing-redient % control ~cm]
3 0 ~
Control 0 0 125 . 0 B 30 0 116.2 8.8 2 130 . 0 + 5 . 0 B -1 E 30 + 5 0 111. 2 13 . 8 3S B ~ E 30 ~ 10 ~ 111. 2 -13 . 8 ~ 1 - 33 -O.Z. 0050/41~34 Crop~ Cot~on (variety: GC - 510) Type of soil: Loam Sowing~ February 28, l9B9 Treatment: June 27, 1989 Evaluation: Plant damage June 6~ 1990 Yield of seed cotton June 6, 1990 Sub~tance g/ha of PlantYield of seed co~ton active damagekg/ha Difference ~rom ingredient ~ control (kg/ha) :
Con~rol 0 0 3233 B 30 0 3375 + 142 30 + 5 ~ 3~53 + 22~
B + E 30 ~ 10 4 4003 ~ 770 B ~ E 30 + 20 3 2693 ~ 540
O.Z. 0050/41834 Synerqistic aqents for requla~in~ ~lant qrowth The present invention relates to agent~ for regulating plant growth, containing a synergistic mixture of one or more growth-ragulating qua~ernaxy ammonium salts from the group consis~ing o~ the compounds I, comprising N,N-dLmethylazacycloheptani~m salt~, N,N
dimethylpipexidinium salts, N,N~dimethyltetrahydro-pyridazinium salts, N,N,N-trimethyl-N-~-chloroethyl-ammonium salts~ N-methylpyridinium salts and N,N-dLme-thylpyrrolidinium salts, and an imiclazolinyl derivativeof ~he ~eneral formula II
R 5~COR 3 I I
R 6 N~R 1 HN O
wh~re R1 i~ Cl-C4-alkyl, R2 i~ Cl-C4-alkyl or C3-C~ CYC1G_ alkyl, R3 iS ~ydrogen, hydro~yl, Cl-Cl2-alkyl, Cl-Cl2-alkoxy, C1-C1~-alkylamino, di-Cl-Cl2-alXylamino or is phenyl t phenoxy or ph~nylamino, where the aromatic radicals may carry from one ~o five halogen atoms and/vr from one to three of the following group~: Cl-C4-alkyl ~
Cl-C4-haloalkyl, Cl-C4-alkoxy, C~-C4-haloalko~r, C~ 4-alXylthio or C1-C4-haloalkylthio, R4 is hydrogen, halogen?
Cl-C4-alkyl, Cl-C4-haloallcyl, Cl-C,,-alkoxy, Cl-C4-haloalkoxy, Cl~C4-alkylthio or C1-C4-haloalkylthio and ~5 and R~ lndepend~ntly of one another are each one of the group~ ~tated for R4 or together form a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atomsand/or from one to three of the following groups: C1-C4-alkyl r C1-C4-haloalkyl, Cl-C4-alkoxy, Cl~C4 haloalko:~y, Cl-C4-alkylthio or Cl-C4-haloal~ylthio, and inert additives.
The present invention furthermore relates to methods ~or regulating plant growth with these agents.
~ uaternary ammonium compound~ are disclosed in the literature as plant growth regulators (DE-A 22 07 575). The li~erature alco describes 'j ,~ ~" ~
- Z - O.Z. 0050~41834 imidazole deriYatives as herbicides ~DE-A 31 21 736).
Mixtures of N,N,N-trimethyl-N ~-chloreethylammonium s~lts and 2-(4-isopropyl-4-methyl-5-oxo-2-Lmidazolin-2-yl)-3-quinolinecarboxylic acid having growth-regulat.ing properties are ~lso known (EP-A 149 083~.
I~ is an ob~ect of the present in~ention to provide novel effective ~ynergistic mixtures for regula~-ing plant growth.
~e have found that this ob~ect is achieved by ~he synergistic mixtures defined at the outset. Method~ ~or u~ing these mixtures as plant growth regulators were also found.
In view of the intended use in the novel syner-~istic growth-regulating agents, suitable substituents of the c~mpound~ II are the following radicals~
R1 is Cl-C4-alkyl, such as methyl, ethyl, propyl, 1-methyleth~l, butyl/ l-methylpropyl, 2-methylpropyl or dimethylethyl, preferably methyl, ethyl or 1-methyl ethyl, in particular methyl or l-methylethyl;
R~ is Cl-C4-alkyl, such as me~hyl, ethyl, propyl, 1-methylethyl, butyl, l-methylpropyl, ~-methylpropyl o~
1/l-~imethylethyl, preferably methyl or ethyl, in par-ticular meth~1, or C3-C6-cycloal~yl, ~uch a~ cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferably cyclopropyl or cyclopentyl, in particular cyclopropyl;
: R3 iY hydrogen;
C1-C12-alkyl, prefsrably branched or straight-chain Cl-C6-alkyl, such as methyl, ethyl, pxopyl, l-methyllethyl, 3~ butyl, l-mathylpropyl, 2-methylpropyl, 1,1-dLmethyllethyl, pentyl., 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2 dimethylpropyl, l-ethylpropyl~ hexyl, 1,1-dimethylpropyl, 1,2-di~ethylpropyl, 1-m~thylpentyl, 2-mekhylpentyl, 3-methylpentyl, 4~methylpentyl, 1,1-dimethylbutyl, 1,2-dlmethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-d:Lmethylbutyl~ 3,3-dimethylbutyl, l-ethylbu~yl, 2-e~hyl-butyl, l,1,2-trimethylpropyl, 1,2,2-trimekhylpropyl, - 3 - O.~. 0050~41834 1-e~hyl-1-methylpropyl and l~ethyl-2-methylpropyl, in particular br~nched or straight-chain Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methyl propyl, 2-methylpropyl or 1,l~dLmethylethyl;
C~-C12-alkoxy, preferably branched or straight chain C~-C6-alkoxy, such as methoxy, ethoxyl propoxy, 1-methyl-ethoxy; butoxy, l-methylpropoxy, 2-me~hylpropoxy, 1,1-dLmethylethoxy, pentyloxy, 1-methylbutoxy, 2-methyl~
butoxy~ 3-methylbutoxy, 2,2-dLmethylpropoxy, 1-ethylprop-oxy, he~yloxy, l,l-dLmethylpropoxy, 1.,2-dLmethylpropoxy, l-me~hylpentyloxy, 2-methylpentylo~y/ 3-mathylpentyloxy, 4~Nethylpentyloxy, 1,l-dimethylbutoxy, 1~2-dimethyl-butoxy, 1~3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbuto~y, 2-lS ethylbuto~y, 1,1,2-trimethylpropo~y, 1,2,2-trimethyl-propo~y, l-ethyl-1-met~ylpropoxy or 1-ethyl-2-methyl-propoxy/ in particular branched or straight-chain Cl-C4-alkoxy, such as methoxy, etho~y, propoxy, l-methylethoxy, : ~uto~y, l-me~hylpropoxy, ~-methylpropo~y or 1,1-dLmethyl-ethoxy;
Cl-Cl2-alkylamino, in particular C1-C6-alkylamino, such as methylamino, ethylamino, propylamino, l-methylethylamino, butylamino, 1-methylpropy~lamino, 2-methylpropylamino, 1,~ dimethyle~hylamino, pentylamino, 1 methylbutylamino, 2-methylbutylamino~3-methylbutylamino,2,2-dLmethylprop-ylamino, l~ethylpropylamino, hexy~lamino, 1,1-d~nethyl-propylamino, 1,2-dimethylpropyl2mino, l-methylp~antyl-amino, 2-m~thylp~antylamino, 3-methylpentylamino, 4-methylpen~ylhmino, ~ dimethylbutylamino, 1,2-dlm~athyl-butylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutyl-amino, 2,3-dimethyl~u~ylamino, 3,3-dimeth~lbutylamino, 1-ethylbutylamino~ 2 ethylbutylamino; 1,1,2-trimethylprop-yl~nino, 1,2,~-trimethylpropylamino, 1 ethyl-l-methyl-~,, propylamino and 1-ethyl-2-methylpropylamino;
di-C1-C12-alkylamino, in particular di-C~-C~-alkylamino, preferably di-Cl-Cb-alkylamino, ~uch a~ N,N~dimethyl~mino, diethylamino, N,~-dipropyl~mino, ~,N-di-(1-methyl-., ;~
, ., ,, .
- ~ - O.Z. 0050/41~34 ethyl)amino, N,N-dibu~ylamino, N,N-di~(1 methylpropyl)~
amino, N,N-di-~2-methylpropyl)-amino, N,N-di-(1,1-dLmethylethyl)-amino, N-ethyl-N-methylamino, N-methyl-N
propylamino, N-methyl-N-(l-methylethyl)-amino, N-butyl-N-methylamino, N-methyl-N~ methylpropyl)-amino, N-methyl-N-(2-methylpropyl)-amino, N-(1,1-d~nethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(l-methylethyl)~amino, N-butyl-N~ethylamino, N-ethyl-N-(l-methylpropyl)-amino,N ethyl-N-(2-methylpropyl)-amino,N-ethyl-N~ d~nethylethyl)-~mino, N~ methylethyl)-N-propylamino, N-butyl N-propylamino, N-(1-methylpropyl)-N propylamino, N~(2-methylpropyl)- N-propylamino,:N-(l,l-dLmethylethyl)-~-propylamino, N-butyl-N-tl-methylethyl) amino, N~ methylethyl)-N-(1-methylpropyl)-amino, N~
methylethyl)-N (2-methylpropyl)-aminol N-(1,l-dLmethyl-ethyl)-N-Il-methylethyl) amino, N-butyl-N~ methyl-propyl)-amino,N-butyl-N~(2-methylpropyl)-amino,N-butyl-N-(l,l-dimethylethyl)-amino, N~ methylpropyl)-N-(2-methylpropyl)-amino, N-(l,l-dLmethylethyl)-N (1 methyl-propyl)-amine and N-(l,l-dLmethylethyl)-N~(2-methyL-propyl)-amino;
phenyl, phe~o~y or phenylamino, where the aromatic radical3 may carry from one to five halogen atoms, such a~ fluorine, chlorine, bromine or iodine, preferably fluorina, chlorin* or bromine, in particular f1UOI ine or chlorine, and/or from one to threa of the following group~:
Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l~methylpropyl, 2-methylpropyl or 1,l-dimethyleth-yl~ praferably methyl, ethyl or 1-methylethyl, in par-ticular methyl;
Cl-C4-haloalkyl, in particular Cl- or C2 haloalkyl, such a~
chloromethyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifl.uoromethyl, chloro1uoro-methyl, dichloro1uoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2l2-difluoroathyl, 2,2,2-tri~ oroethyl, 2-chloro-2-fluoroethyl, ~ 5 - O.Z. 0050/41834 2-c~loro-2,2-difluoroethyl, 2,2-dichloro~2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl, preferably difluoromethyl or trifluoromethyl, in particular tri-fluoromethyl;
Cl-C4-alkoxy, such as methoxy, ethoxy, propoxy, 1 methyl-ethoxy, butoxy, l-methylpropoxy, ~methylpropoxy or 1,1-dLmethylethoxy, preferably methoxy, ethoxy, 1-methyl-ethoxy or 1,1-dLmethyletho~y, in particular metho.~y or 1-methylethoxy;
Cl-C4-haloalkoxy, in particular Cl- o:r C2-haloalkoxy, ~uch as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluorometho~y, chloro~
fluoromethoxy,dichlorofluoromethoxy,chlorodi1uorometh-oxy, 1 fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroe~hoxy, lS 2,2,2-trifluoroe~ho~y,2-chloro-2-fluoroethoxy,2-chloxo-2,2 difluoroethoxy, 2,2-di~hloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or pentafluoroetho~y, preferably di-fluorometho~y or trifluorome~ho~y;
Cl-C4-alkylthio, such as methylthio~ ethylthio, propyl-~0 thio, l-methylethylthio, butylthio, l-methylprop~lthio, 2-methylpropylthio or l,l--dLmethylethylthio, preferably methylthio, or C1-C4-haloalkylthio, in particular C~ or C2 haloalkyl-thio, ~uch as chloromethylthio, dichlorome~hylthio, txichloromethylthio, fluoromethylthio, difluoromethyl-thio, trif luoromethylthio, chlorofluoromethylthio~
dichlorofluoromethy~thio, chlorodifluoromethylthio, 1-fluoroethylthio, 2 fluoroethyl~hio, ~,2-difluoroethyl-thio, 2,2, 2-trif luoroethylthio, 2-chloro-2-fluoroethyl thio, 2-chloro-~,2-difluoroethyl~hio, 2~2-dich:Loro-2-fluoroethylthio, 2,2,2-trichloroQthylthio or penta-fluoroethylthio, preferably difluoromethylthio;
R4 is hydroyen;
halogen, such as fluorine, chlorine, bromine or iodine, ; 35 pre~erably ~luorine, chlorine or brominet in paxticular ~luorine or chlorine;
Cl-C4-alkyl/ such as methyl, ethyl, propyl, 1-methyle~hyl~
~ ' - 6 - O.Z. 0050/~1834 butyl~ l-methylpropyl, 2-methylpropyl or lrl-dlmethyleth-yl, preferably m~thyl, ethyl or l-methylethyl or 1,1 dimethylethyl;
C1-C4-haloalkyl, in particular Cl~ or C2-haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifluoromethyl, chlorofluoro-methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1~
fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2 difluoroe~hyl, 2,2-dichloro-2-fluoroethyl, 2,2,2 tri-chloroethyl or pent~fluoroethyl, preferably difluorometh-yl or trifluoromethyl, Cl-C4-alkoxy, such as metho~y, ethoxy, propoxy, 1 methyl-ethoxy, buto~y, l-methylpropoxy, 2-methylpropoxy or 1,1-dLme~hyletho~y, preferably metho~y, ethoxyl 1-methyl-ethoxy or 1,1-dLmethyletho~y, in particular methoxy or l,1-dLmethylethoxy;
Cl-C4~haloalkoxy, in particular C~- or C2-haloalkoxy, such as chloromethoxy, dichloromethoxy, tr.ichloromethoxy, ; 20 fluoromethoxy, difluorometho~y, trifluoromethoxy, chloro-fluoromethoxy r dichlorofluorometho~y,chlorodifluorom2th-oxy, 1 fluorosthoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2/2,2-trifluoroe~hoxy,2-chloro~-fluoroethoxy,2-chloro-2,2-difluoroetho~y, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or pentafluoxoethoxy, preferably di-fluoromethoxy or ~rifluorome~hoxy;
Cl-C4-alkylthio, such as methylthio, ethylthio, propyl-thio, l-methylethylthio, butylthio, l-methylpropylthio, 2-methylpropylthio or l,l-dLmethylethylthio, preferably methylthio or ethylthiof or C1-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-thio, such a3 chloromethylthio, dichloromethylthio, tr~chloromethylthio, fluoromethylthio, difluoromethyl-thio, triEluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethyl-thio, 2,2,2~rifluoroethylthio; 2-chloro-2-fluoxoethyl-- 7 - o.Z. 0050/41834 thi~, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroe~hylthio, 2,2,2-trichloroethylthio or pentafluoroethylthio, preferably difluorome~hylthio, and R5 and R6 independnetly of one another are each one of the groups stated in general and in particular for R4 or together form a 1,3-butadi0ne-1,4-diyl group which may carry from one to four halogen atom~3, such as fluorine, chlorine, bromine or iodi~e, preferably fluorina, chlor-ine or bromi~e, in particular fluorine or chlorine, and/or from one to three of the following groups:
Cl-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methylpropyl, 2-meth~lpropyl or l,l-dLmethyleth-yl, preferably methyl, ethyl or l-msthylethyl;
Cl C4-ha}oalkyl, in particular Cl- or C2-haloall~yl,~3uch as chloromethyl, dichloromethyl, trichloromethyl, fluoro~
methyl, difluoromethyl, trifluoromethyl, chlorofluoro-methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2~2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-~-fluoroethyl, 2-chloro~2,2-difluoroethyl, 2,2-dichloro-2-flu~roethyl, 2,2,2-tri-chloroethyl or pentafluoroethyl, preferably ~i~luorometh-yl or trifluoromethyl;
Cl-C4--alkoxy, ~uch a~ methoxy, etho~y, propoxy, l-methyl-ethoxy, butoxy, 1-methylpropoxy, 2-methylpropo~y or 1,1-dLmethylethoxy, preferably methoxy, ethoxy, l-methyl-athoxy or l,l-dLmethylethoxy;
C1-C4-haloalko~y, in particular Cl- or C2-haloalkoxy, such : as chloromethoxy, dichloromethoxy, trlchloromathoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro-fluoromethoxy,dichlorofluoromethoxy,chlorodifluorometh-oxy, 1-fluoxoethoxy, 2-~luoroethoxy, 2,2-difluoroethoxy, 2,2,2 trifluoroetho~y,2-chloro-2-fluoroethoxy,2~chloro~
2,2-difluoroethoxy, 2,2-dichloro-2-~luoroethoxy, 2,2,2-trichloroethoxy or pentafluoroethoxy, pref~rably di-fluoromethoxy or trifluoromethoxy;
C1-C4-alkyl~hio, ~uch a~ methylthio, et.hylthio, propyl-thio, l-methylethylthio, butylthio, l-methylpropylthlo, , , , - 8 - O.Z. 0050/4183~
2-methylpropylthio or 1,1-d~nethylethylthio, preferably methylthio or Pthylthio, or Cl-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-thio, such as chloromethylthio, dichloromethylthio, trichloromethylth.io, fluoromethylthio, difluoromethyl-thio, trifluoromethylthio, chloro~luoromethyl~hio, dichlorofluoromethylthio, chlorodifluoromethylthio, l-fluoroethylthio, 2-fluoroethylthio/ 2,2-difluoroethyl-thio, 2,~,2-trifluoroethylthio~ 2-chloro-2-fluoroethyl thio, 2-chloro-2,2-difluoroethylthio, 2,2 dichloro-2-fluoroethylthio, 2,2,2-trichloro~thylthio or penta-fluoroethylthio, preferably difluoromethylthio.
In view of the intended use in the synergis~ic agents, particularly preferred compounds II are those in which ~he substituents have the following meanings-R1 is C1 C~-alkyl as stated above, in particular methyl;
R2 is Cl-C4-alkyl as sta~ed above, in particular methyl or 1 methylethyl, or C3-C6-cycloalkyl as stated above, in particular cyclo-propyl;R3 i~ hydrogen; hydxoxyl;
Cl-C8-alkyl a~ stated abo~e, in particular branched or straight-chai~ Cl-C6-alkyl a~ stated above;
Cl-Ca-alkoxy a~ ~tated above, in particular branched or straigh~-chain Cl C~-alkoxy a~ s~ated above;
C1-C~-alkylamino as stated above, in particular Cl-C6-alkylamino a~ ~tated above;
di-Cl-C8 alkyl~nino as stated a~ove, in particular di-Cl-C4-alkylamino as stated a~ove;
phenyl, phsnoxy or phenylamino, where the aromatic radicals may carry from one to ~ive halogan atoms as stated above, ln particular fluorine or chlorine, and/or from one to thres of the following groups:
Cl-C4-alkyl as stated above~ in particular methyl;
C1-C~,-haloalkyl as sta~ed above, in particular difluoro-methyl or ~rifluoromethyl;
C1-C4-alko~y as ~tated above~ in particular methoxy .
.' .
.
. ~ ; . ,.
g ~ O.Z. 0050/~1834 ethoxy, 1-methylethoxy or l,1-dLmethylethoxy, Cl C4-haloalkoxy as stated above, in particular difluoromethoxy or trifluoromethoxy;
Cl C4-alkylthio as stated above, in particular methylthio or ethyl~hio, and C~-C4-haloalkylthio as stated above, in particular difluoromekhylthio;
R4 is hydrogen;
halogen as stated above~ in particular fluorine or chlorine;
Cl-C4-al3~yl as ~tated above, in particular methyl or 1,1-dLmethylethyl, Cl-C4-haloalXyl as stated above, in particular difluoro-- methyl or trifluoromethyl;
C1-C4-alkoxy as stated above, in particular methoxy or l,l-dimethylethoxy;
C~-C4-haloalkoxy a~ ~tated above, in particular difluoro-; methoxy or trifluoromethoxy;
C~-C4-al~ylthio as ~tatad above, in particular methylthio or ethylthio, or C1-C4-haloalkylthio as stated above, in particular di~luoromethylthio, and R5 and R~ indepedently of one another are each one of ~ha groups ~tated in general and in particular for R4 or togethar fonm a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atom~ as stated above, in ~rticular fluorine or chlorine, and/or from one to three of the following groups:
C~-C~-alkyl a~ stated above, in pa.rticular meth~l;
C'1~C4-haloalkyl as ~tated above, in particular trifluoro-methyl;
Cl-C4-~al3coxy a~ s~ated above, in particular methoxy;
Cl-C4-haloalkoxy a~ stated above, in particular difluoro-methoxy or trifluorome~ho~y;
C1-C4-al3~ylthio as ~tated above, in paxkicular met.hylthio, and C~-C4-haloalkylthio as stated above, in particular difluoromethylkhio.
- 10 - O.Z. 0050/41~34 Particularly preferred synergistic agen s for regulating plant growth are those which contain an N,N-d ~ ethylpiperidinium salt or an N,N,N trimethyl-N 2-chloroethylammonium salt as the growth-regulating quater-nary ammonium salt.
Particularly prefarred ~nergistic agents of thi~
type are ~hose which contain, in addition ~o the N,N-dime~hylpiperidinium salt~ or N,N;N-trimethyl-N 2-chloro~
ethylammonium salts, an Lmidazolinyl derivative of the general formula II, where R1 is C1-C4-alkyl as stated ahove, in particular methyl;
R2 i~ C1-C4-al ~ 1 as stated above, in particular methyl or l-methylethyl, or C3-C6-cycloal ~ 1 a stated above, in particular cyclo-p~pyl;
R3 is hydrogen; hydroxyl;
Cl-C~-alkyl as stated above, in particular branched or straight-chain C1-C:~-alkyl a~ stated above;
C1 Ct~-alkoxy as stated above, in pa.rticular branched or 2 0 straight-chain C1-C6-alkoxy as st~te~ abo~e, C1-CB-a~ nO a~ stated above, in particular C1-C6-alkylamino as stated above;
di-Cl-Ca-alkylamino a~ stated above, in particular di-C1-C4-alkylami~o as ~tatsd above~ or phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms as ~tated above r in particular f luorine or chlc~rine, _., and/or from one to three of the following groups:
C1-C4-alkyl a~ ~tated above, in particular methyl, Cl-C4-haloalkyl a~ stated above, in particular difluoro-methyl or trifluorome~hyl;
Cl~C4-alko~y a~ statad above, in particular metho~y or ethox~;
C1-C~-haloalko~y a~ stated above, in particular difluoro-methoxy or ~rifluorometho~y;
C1-C4-alkylthio a stated above, in paxticular methylthio or ethylthio, ?
~ O.Z. 0050/41~34 and C,-C4-haloalkylthio as stated above, in particular difluoromethylthio;
R4 is hydrogen or halogen as stated above, in particular fluorine or chlorine, and Rs and R6 independently of one another are each hydrogen;
halogen as stated above, in part:icular ~luorine or chlorine;
Cl-C4-alkyl as stated above, in particular methyl;
Cl-C4 haloal~yl a ~tated above, in particular trifluoro-methyl;
Cl C4 alkoxy a3 stated above, in particular methoxy or I t l-dimethyletho~y;
Cl-C4-haloalkoxy as stated above, in particular difluoro-methoxy or trifluoromethoxy;
Cl-C~-alkylthio a~ ~tated abo~e, in particular methylthiot :~ or Cl-C4-haloalkylthio as stated above, in particular difluoromethyl~hio, or tog0~her form a 1,3-butadiene-1,4-diyl gxoup which may carry from on~ to four halogen atoms as stated above, in : particular fluorine or chlorine, and/or one of the following groups.
Cl-C4 alkyl a~ st ted above, in particular methyl;
: 25 Cl~C4-haloalkyl a~ ~ated above, in particular trifluoro-methyl;
Cl-C4-alkoxy as stated abo~e, in particular methoxy;
C1-C4-haloalkoxy as ~tated above, in particular difluoxo methoxy or trifluorometho~y;
Cl~C4-alkylthio as stated above, in particular methylthio, or Cl-C4~haloalkylthi.o as stated above, in particulax difluoromethylthio.
~'he active ingredients can be applied together or separately, at the ~ame time or in succession~ before, ; 35 duxing or after ~mergence o~ the plan-ts.
In the syner~istic agent~, the weight ratio of ~mmonium salt I to imidazoli.ne derivative II is from - 12 - O.Z. 0050/41834 0.1 . l to 1000 : 1, preferably from 1 : 1 to 950 , 1, in particular from 1.5 : 1 to 920 : 1.
The novel agents can be used, for example, in ~he form of directly sprayable solutions, powders, suspen-sions, including concentra~ed Aqueous, oily or other suspensions or dispersions, emulsions, oil dispersion~, pastes~ dusting agents, broadcasting agents or granules, by spraying, atomi ing~ dusting, broadcasting or pouring.
The application forms depend on the intended uses. Th~y should in any case ensure a very fine distribution of the novel active ingredien~s.
The compounds I and II axe suitable in general for the preparation of directly sprayable solution~, emulsions, pastes or oil dispersions. Suitable inert additive~ are mineral oil fractions ha~ing a medium ~o high boiling point, such a~ kero~ene or diesel oil, and coal tar oil~ and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbon~, eg. toluene, xylene, paraf~inr tetrahydronaphthalene, alkylated naph~halenes or derivative3 thereof~ methanol, ethanol, propanol, butanol/ cyclohexanol, cyclohexanone, chloro-benzene, i~ophorone or strongly polar solvents, such as ~,N-dimethylformamide, dimethyl sulfoxide, N-methyl-pyrrolidone or water.
Aqueous application forms can be prepared from emulsion concenkra~, dispersion~, pastes, wettable powders or water-disper~ible granules by adding water.
For the preparation o emulsion~ t paste~ or oil dispar-sion~, the ~ubstrates, a~ such or dissolved in an oil or sol~ent, can be homogenized in water by means o wekting agent~, adherents, disper~ant~ or emul~ifier~. Howev9r, it i3 also possible to prepare concentrates which con~ist o~ activ~ ~ubstance, wetting agent~, adherents, di~per-san-t~ or emulsl~ier~ and possibly 301~ent or oil and which are suitable for dilution with water.
Suitable surfactant~ are the alkali metal, alkaline earth metal and ammonium salts o~ aromatic - 13 - O.Z. 0050/41834 sulfonic acids, for example lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkylsulfonate~ and alkylarylsulfonates, alkylsulfate~, lauryl ether sulfates and fatty alcohol sulfates, and ~alts of sulfated hexa-, hepta- and octa-decanols, and of fatty alcohol glycol ethers, condensate~
of sulfonated naphthalene and its derivatives with formaldehyde~ condensates of naphthalene or of naph-thalenesulfonic acids with phenol and formaldehyde~
polyoxyethylene oc~ylphenol ethers, ethoxylated isooctyl,- octyl- or nonylphenol~ alkylphenol polyglycol ether~, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated cas~or oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, ligninsulfite waste liquors or methylcellulose.
Powders, broadcasting agents and dusting agents can be prepared by mixing or milling the active sub-stances together with a solid carrier.
Granules, for example coa~ed, Lmpregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earth~, such as silica gel, silicas, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, kie~elguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea3, and vegetable products, such as grain flours, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carrier~.
~he formulations contain from 0.1 to 95, prefer-ably from 0.5 to 90, % by weight of the active in-gredients. The active ingredients are used in a purity of from 90 to lO0~, preferably from 95 to 100% (according to the NMR spectrum).
~he growth regulators or the active ingredients O . Z . 0050/41834 can be applied by the preemergence or postemergence method. If the active ingredients are less well tolerated by certain crops, it i~ pos~ible to use application methods in which the herb.icides are sprayed 5 with the aid of sprayers in such a way that as far as poss.ible they do not come into contact with the leaves of the sensitive crops while the active ingredients reach the leaves of undesirable plant~ g:rowing underneath or the uncovered soil surface ~post-directed, lay by).
The application rates of active ingredient mixture are from 0.01 ~ 0.01 to 2 ~ 0.001, preferably front 0 . 03 + O . 02 to 1 + O . 001, kq/ha of active substance (a.s.), depending on the s~a~on, target plants and stage of grow~h.
The synergistic mixtures can influence virtually all ~tage3 of development of a plant in di~ferent ways and are therefoxe used a~ growth regulators. The range of activity of the plant growth regulators depend~ in particular a) c7}1 the plant ~pecies and variety, b) on the time of application~ ba~ed on the stage of development o~ tha plant, and on the ~ea~on, r) on the place and method of application (for example s~ed dre~ing, ~oil treatment, foliage application or trunk in~ection in .he case of trees), d) on climatic ~actors, eg. temperature, amount of _ precipitation and also length of day and light inten~ity, e) on the soil quality ~including fertilizer applica-tion), f) on the formulation or application form of the active ingredient and finally g) on the ~oncen~rations in which ~he active substance is used.
From ~he various possibl.a applications of the novel agents in cultivation, in agriculture and in hortictllture, ~ome are mentioned below.
- 15 - o.Z. 0050/~1834 A. The vegetative growth of the plant~ can be greatly inhibited with the compounds which can be used according to the invention, this being manifested in paxkicular in a reduction in the growth in length. The treated plants accordingly h ve a stunked growth; more-ov~r, a darker leaf coloration is ob~erved.
Reduce~ intensity of growth of yrasses along road edges, hedges and canal banks and on lawn area~, such as parks, sports grounds, orchards, ornamenkal lawn~ and airfield~, proves advantageous in practice, enabling the labor-inten~ive and expensive cutting of lawns to be rsduced.
The increase in the strength of crop~ su~c~ptible to lodging, such a~ cereals, corn, sunflowers and soy-bean, is also of economic interest. The re~;ultingshortening and strengthening of the stem reduce or slLminate the danger of lodging (of bending) of plants - under unfavorable weather conditions prior to harvesting.
The u~e of growth regulator~ for inhibiting the growkh in length and for changing $he tLme of ripening of ootton iB also importan~. This permit~ completely mechanized harvesting of thi~ important crop.
In the ca3a of fruit tree~ and other trees, the growth r~gulators permit a reduction in cutting cost~.
~oreover, the alternance of fruit trees can be broken by growth ragulators.
The lateral branching of the plants can also be increased or inhibited by the u~e of grow~h regulators.
Thi~ is of interest if, for example, in the case of tobacco plants, it i~ intended to inhibit the formation of ~ide ~hoot~ in favor of leaf growth.
The ~rost rasi~tanco can also be considerably lncrea ed with growth regulator3, for example in wintar rape. On the one hand, the growth in length and the development of a leaf or plant mas~ which i3 too luxuri-ant (and hence particularly su~ceptible to fro3t) are inhibited. On the other hand, the young rape plants are 16 - O.Z. OOS0/41834 held back in the vegetative stage of development after sowing and before the onset of the winter frosts~ in spite of favorable growth conditionst This also elLmina tes the danger of fro~t to plants which tend to ~xhibit a premature decline in ~he inhibition of blooming and to go over into the genPrative phase. In other crops too, for sxamplP winter cereals, it is advantageous if the stocks are well tillered in the fall as a result of treatment ~ith novel compounds bul: do no~ en~er thP
winter with too luxllriant a growt.h. This makes it possible to avoid high sensitiYity to frost and, owing to the relatively small leaf or plant mass, attack by various diseasP~ ~ fox example fungal disease). Inhibi tion of the vegetative growth furthermore permits denser planting of the soil in the case of many cxop~, making it possible to achieve a greater yiel , ba~ed on soi:L area.
. The growth regulators make it possible to achieve greater yield both of plant part~ and of plant in-gredient~. For example, it i~ po ~ible to induce the grow~h of laxger amounts o bud~, blooms, leaYes, fruits, seeds, roots and tuber~, to increase the content of sugar in sugar beet~, sugar cane and citru~ fruits, to increase . the protein content of cereal~ or soybean or to stLmulate greater lat~x flux in rubbsr tree~.
By intervening in the plant metaboli~m or by prcmoting or inhibiting vegetative and/or generative growth, -the synergistic agents can result in increased yield~, C. Finally, both shortening or lengthening of the 8taga9 of development and acceleration or re~ardation o~
the ripening of the haxvested plant parts bsfore or after harve~ing can be achLeved with plant growth regula~or~.
For example, it is of economic interest to facilita~e harve~ting, thi~ being pe~litted by con-centrated dropping or reduction in ~the adhesion to the tree in the ca~e of citrus fruit~, olive~ or other specie~ and varieties ~f pomes, drupes and hardshall ;
- 17 ~ O.Z. 0050/~1834 fruit. The same m~chanism, ie. promotion of the forma-tion of absci~sion tissue between the fruit or leaf part and the sprout part of the plant is also essential for readily controllable defoliation of crops such as for example cotton.
D. Furthermore, the water consumption of plants c~n be reduced with growth regulators. This is particularly important for agricultural areas which have to be artifi-cially irrigated at great expense, for example in arid or semiarid regions. By using the novel ~ubstances, it is po~sible to reduce the intensity of irriga~ion and hence to carry out more economical farming. Under the influ-ence of growth regulators, the available water is bet~er utilized becau~e, in~er alia, 15 - ~he extent of opening of the stomata is re~uced, - a thicker epidermi~ and cuticula are formed, - root penetration o~ the soil i~ improved and - the microclLmate in the crop is advantageou~ly affected by more compacted growth.
The novel synergis~ic agents c~n be fed to the crops both via the seed ~as seed dre~sings) and via the soil, ie. through the root and, particularly preferably, via the foliage by spraying.
Because of the good toleration by plants, the application rate can ba greatly varied.
In view of the wide range of applica~ion methods, the novel agents can be used in cere 1 crops and cotton.
The synergi~tic effect can be determined by the formula of S.R. Colby (Wa~ds 15 (1967), 20~2) E = X ~ Y - X Y / 100 where the variables have th~ following meanings:
X 18 the ~ea~urable effect of the active ingredient I at an applica~ion .ra~e ~a], ; Y is the mea8urable efEect of the active ingredient II at an appl~cation rate ~b] and is the expected measurable efect of a mixture of active ingredient I at the application rate ~a] and of j;, , ! , ~;, . ..
- 18 ~- O.Z. 0050/41834 active ingredient II at the application rate ~b].
From the difference between the expected v~lue ~
according to Colby and the measured value, it is possible ~o determine whether there is a synergistic efect (reinforcement of the effect ox increase of activity) or an antagonistic effect (weakening of the effect or reduction in activity), or if there are merely additive effec~s on the activity, this being the case if the two values correspond.
The Lmproved biological action of the mixtures compared with the individual substances in cereal crops and cotton can be demonstrated in field trials.
Various mix~ures of th~ following compouncls were inves~igat~d:
A
N~N,N~Trimethyl-N-~-chloroethylammoniumchloride(chloro-mequat chloride) N,N-DLmethylpiperidinium chloride ~mepiquat chloride) C
2-~4-Isopropyl-4-methyl-5-oxo-2-imidazolin 2-yl)-3-quinolinecarbo~ylic acid (imazaquin) D
I~opropylammonium 2-(4-isopropyl-4-methyl-S-oxo-2-imidazolin-2~yl)~3-nicotinecarboxylate (imaæapyr) : E
5-Ethyl 2-(4-isopropyl-4-methyl 5-oxo-2-imidazolin 2 yl)-3 nicotinecarbo~ylic acid (imazethapyr) ~he trial~ were carried out on plots, each measuring 12.5 m2 (cereals) or 50 m2 (cotton), with 4 replicates in each ca~e. Cultivation, ~ertilizer ap-plication and the use of crop protection agent~ again~t growth of weeds and attack by fungi and by in~ect pes~s were carried out in a manner conventional ~or t~le location.
The novel agent~ were applied by the post-emergence method (3.5 bar, 400 l/ha of water).
~ '` l"`1 r r - 19 - - Z ~ 0(~50/41~33 The ~bovemPntioned cexeal trial~ show that the novel mixtures are clearly superior to the known mixture A ~ C (EP-A-149 083). Furthenmore, Ta~le 2 shows that a mixture consisting of two diferent quaternary ammonium compounds with a triazole has an action superior to that of ~he known combination of A + C.
TABL~ 1 Crop: Winter barley (variety: Marinka) Type of soil: Clayey loam Sowing: Saptember 28, 1988 Treatment: March 28, 1989 Evaluation: Plant damage Nay 12, 1989 Height of growth May 17, 1989 Sub~tance g/ha of Plant Height of grow~h active damage cmDif~erence rom ingredient % control ~ (cm)_ Control - 0 102.1 A 690 0 101.60.5 D 10 5 72.5- 29.6 A + D 6gO ~ 5 6 71.9 - 30.2 A + D 690 ~ 10 6 57 4 6 - 44.5 A + D 690 ~ 20 11 41.4- 60.7 A ~ C 759 ~ 16.5 3 84.0- 18.1 ~ ~ C 1150 + 25 10 78.9- 23.2 - 20 - OOZ~ 0050/4183 Crop: Winter wheat (variety Baroudeur) Type of soil: Clayey sand Sowing: October 2, 1989 Txeatm~nt: March 28, 1990 Evaluation: Plant damage May 17, 1990 Height of growth June 5 t 1990 Substance g/ha of Plant Height of growth active damage cm Difference from ingredient % control ~ . (cm) Control 0 0 108.0 A + E 920 + 1 0 100.8 - 7.2 A + E 920 t 2 0 99O2 - 8.8 A + E 920 ~ 4 0 99.8 - 8.2 ?
A ~ B ~ E 690 + 230 ~ 20 100.5 - 7.5 A + C 920 + 2 0 101.0 7.0 T~BLE 3 Crop: Winter wheat (varietyO ~axoudeur) ~ype of ~oil: Sandy loam Sowing: October 12, 1989 Treatment: March 5, 1990 Evaluation: Plant da~age June 6, 1990 : Internodal length Ju~e 6, 1990 Ear length June 6, 1990 Substance g/ha o Plant Internodal length Ear length active damage cm Dif~erence cm Difference ingredient ~ fxom con~rol From control cm cm ~
Control 0 a 5.2 8.4 A ~ C 920 -~ 2 0 3.B - 1.4 8.3 ~.l A -~ E 920 ~ 2 0 3.5 - 1.7 8.5 +0,1 . . :
:., -. , , ~ . '' :` :
- 21 - O.Z. 0050/41834 Crop: Winter wheat (variety: Baroudeur3 Type of soil: Sandy loam Sowing: October ~, 1989 Treatments March 1, 1990 Evaluatîons Plant damage May 10, 1990 Height of yrowth May 10, 1990 Substance g/ha of Plant Height of growth active damage cm Difference from 13 ingredient ~ con~rol ~cm) Control 0 0 96.7 A ~ C 920 + 2 0 ~7.6 ~ 9.1 : 15 A + E 920 ~ 1 0 86O2 ~ 10.5 A + E 920 ~ 4 0 86.9 - 9.8 _ , - 22 - O. 2 . 0050/4183 Crop . Winter wheat ( vari ty: Rraka Type of soil: Loamy sand Sowing : November 7, 1 9 8 9 Treatment: April 2, 1990 ~valuation: Plant damage June 6, 1990 Height of growth June 6, 1990 Substance g/ha of Plant Height of growth active damage cm Diffç?rence from ingredien~ % control ( cm Control 0 0 117 . 0 B 690 0 107 . 0 - 10 . 0 1~ C 5 0 11~.5 ~ 1.5 B ~ C 690 + 2 . 5 0 lG6 .1 -10 . 9 A + C 690 ~ 15 0 106 . 9 - 10 .1 EXANPI.ES 6 AND 7 The ~ynergistic e~fect of ~he mixture A + D is demon~trated using barley. It is noted that the addition oiE > 10 g/ha of active ingredient o~ ~ubstance D can lead to plant damage.
.
' ' , - 23 - O.Z. 0050/41834 Crop: Su~mer barley (variety: Gimpel) Type of ~oil: Clay Sowing: March 20, 1989 Treatment: May 18, 1989 Evaluation: Plant damage June 2, 1989 Height of growth Juns 12~ 1989 Substance g/ha of Plant Height of growth active damage cm Difference from ingredient % control ~cm) Control 0 0 101.2 A 690 0 9fi.9 ~ 4,3 D 10 5 55.6 - 45.6 A ~ D 6~0 ~ 5 7 44.6 ~ 56.6 A ~ D690 ^~ 10 8 42.9 - 58.3 A + D690 t 20 8 42.5 - 58.7 TABL~ 7 : 20 Crops Winter barley (variety: Igri) Type of soil: Very clayey loam Sowingo September 22, 1988 Trea~ment: Rpril 21, 1990 Evalllation: Plant dama~e May 15, 1989 : 25 Height of g~owth MAY 22, 1989 Substance g/ha of Plant Height of growth _ active damage cm Difference from ingredien~ % control (cm) .... ~
Control 0 0 111O2 ~90 0 111.2 0 D 10 12 82.0 - 29.2 A + D 690 ~ 10 21 71.2 - 40.0 A ~ D 690 -~ 20 54 63.8 - 47.4 _ ~4 ~ 0.2. 0050/41~34 ~XAMPLES 8 TO 10 In the case of wheat and barley, the mixture A -~
E also leads to synergistic shortening of the stem, im-proved strength and correspondingly greater yields.
Crop: Summer wheat (variety: Ralle) T~pe of soil: Clay Sowing: March 20, 1989 Tre~tmen~. May 18, 1989 Evaluation: Plan~ damage June ~, 1989 Height of growth June 130 1989 Substance g/ha of Plant Height of growth active damage cm Differ~:nce from ingredient ~ control (cm) Control 0 0 7g.8 A 690 0 63.0 - 16.8 E 10 0 7~.8 - 1.0 A + E 690 ~ 5 0 50~1 - 19.7 A + E69~ ~ 10 0 57.8 - 22.0 E690 + 20 4 56.0 - 23.8 TABL~ 9 Crop: Summer wheat (variety$ Ralle) Type of soil: Loam~ ~and Sowing~ February 21, 1989 Tre~ment: ~ay 12, 1989 Evaluation: Plant damage Jun~ 21, 1989 Height of growth Augu~t 3, 1989 Substanca g/ha of Plant Height o~ gxowth active damage cm Differerlce from ingred.ient % control ~cm) Control0 0 36.2 6~ 0 36.8 ~ 0.~
E 10 0 3~.5 - 1.7 '' ' .
.
- 25 - O.Z. 0050/41834 A + E 690 ~ 10 0 39O1 + 2.9 Crop: Winter barley (varietyo Igri~
Type of soil: Very clayey loam Sowing: September 22, 1989 Treatment/ April 21, 1989 Evaluation: Plant damage May 15, 1989 Lodging July 5, 1989 Grain yield 3uly 11, 198g 10 Substance g/ha of Plant Lodging/ Grai~ yield/
active damage difference ~iff~rence ingreclient from control frc~ con~l % ~%] [%]
. . .
Control0 0 46 75.5 690 0 48 + 2 69.7 5.8 0 ~ + ~ 69.3 - 6.2 A + E690 + 10 0 34- 12 76.9 ~ 1.4 A + E690 + 20 0 3610 76.2 ~ 0.7 Mixkures consisting of compounds B + C lead to a synergistic inhibition of growth in barley, whsat and cotton. The resulting improved strength is illu~trated by Exampl~ 13.
- 26 - 0.~. OGSO/41834 TABLE ll Crop: Summer wheat (variety Ralle) Type of ~oil: Clay Sowing: March 20, 1989 Treatment: May 19, 1989 Evaluation: Plant damage June 22, 1989 Height of growth June 13, 1989 Substance g/ha ofPlant Height of growth activedamage cm Difference from ingredient ~ co~trol (cm) .. _ . . ~
ControlO 0 80.6 B 690 0 66.0 ~ 14.6 C 10 0 ~l.O + 0.4 : ~ ~ C690 + lO O 61.5 - 19.1 B + C690 + 20 7 49~8 - 30.8 ~ABL~ 12 Crops Winter wheat (variety: Kraka) Type of soil: Loamy sand Sowing: November 7, 1989 Tr~atment: April 30, 1990 . Evaluation- PLant damage June 5, 1990 Heigh~ of growth June 5, 1990 Substance g~ha ofPlant Haight of growth active damage cm Diff~rence from _ ingredient ~ control (cm) Control O 0 9S.1 B 690 0 86.0 - 9.}
C 5 0 95.4 ~ 0.3 B + C 690 ~ 1.25 0 80.3 - 14.8 B + C 6gO ~ 2.5 0 84.0 - 11.1 B + C 690 + 5.0 0 84.5 - 10.6 ,, .
- 27 - O.Z. 005~/41834 Crop: Summer barley ( varie-ty O Gimpel ) Type of soil: Clay Sowing O Marc h 2 0, 1 9 8 9 Treatment: May 18, 19 8 9 Evalua~ion: Plant damage June 2, 198 Height of growth :rune 12, 198 Lodging July 2 4, 19 8 9 Sub~tance g/ha of Pla.nt Height o:E Lodging~
active damage growth~ dif ference ingredient ~ difference from control from control [cm]
[cm]
Control 0 0 95 . 4 38 B 690 0 94 . 4 -1 G 0 4g + 11 C 10 0 91 O 0 -4 . 4 ~0 ~ 2 B + C 690 + 5 0 82 . 2 -13 . 2 0 - 38 B ~ C 690 + 10 14 61. 6 -33 . 8 0 - 38 B + C 690 ~ ~0 14 S4 ~ 8 -40 . 6 0 - 38 Crop: Cotton (variety: SJ - 2 ) Type o~ soll s Sandy loa~
Sowing: ~ebruary 24, 1989 25 Treatmen$ - June 2~, 198g Evaluations Plant damagl3 July 6, 1989 Heiçrht of growth October 5, 1989 Sub~tance ~/ha of Plant Height of growkh active damage cm Difference from ingredient ~ control ~cm]
Control 0 0 125 . 0 B 30 0 116 . 2 -8 . 8 C 10 0 12~.2 ~1.2 B+ C 30 ~ 5 0 ill . 2 -13 . 8 B~ C 30 ~10 0 110 . 5 -14 . 5 13+ (~ 30 ~~0 0 107 . 5 -17 . 5 ,.i j .,,, ,1,.
- 28 - O.Z. 0050/~1834 CropO Cotton (variety- Stoneville sa5 ) Type of soil: Sandy loam Sowing: May 26, 1989 Treatment: July 24, 1989 Evaluation: Plant damage July 31, 1989 Substance g~ha of Plant Height of growth active damage cm Differ~nce from ingredient % control [cm]
Control 0 0 121.2 B 60 0 111.0 - 10.2 ~ 10 0 122.8 + 1.6 B ~ C 60 + 5 0 112.5 - 8.7 B ~ C 6Q + 10 0 lOg.8 - 11.4 B ~ C 60 + 20 0 107~5 - 13.7 Mixture~ o substances B + ~ also lead to a æmaller plant height and grea~er yield~ in the case of barley, wheat and cotton.
~ Crop: Summer wheat (variety: Ralle) .~ Type of soil 5 Loamy sand Sowing: Augus~ 15, 1989 Z5 ~reatment: August 15, 1989 Evaluations Plant damage June 2, 1989 ~Ieight of growth A~gust 3, 1989 Sub~tance g/ha of Plant Hsiyht of growth active dama~e cm Dif~erence from ingredient % control [cm]
Control 0 0 38.0 B 690 0 40.5 -~ 2.5 D 10 0 38.4 + 0.4 B -~ D690 + 5 0 44.6 + 6.6 B -~ D690 -~ ln 0 40.1 + 2.1 B + D690 t 20 5 31.0 - 7.0 I `' ` ~ "' . ' ! .
- 29 - O.Z. 0050/41834 Crop: Summer barley (~ariety: GLmpel) ~ype of soil: Clay Sowing: March 20, 1989 Treatment May 18, 19 8 9 Evaluation: Plant damag~ June 2, 1989 Heigh~ of grow~h June 12, 1989 Substance g/ha of Plant Height of growth active dam~ge cmDifference from ingredient % control ~cm]
Control 0 0 g5.4 B 690 0 94.4 - 1.0 D 10 5 51.8 - 43.6 B + D 690 -~ 10 0 43.9 - 51.5 B + D 690 + 20 6 43.5 51.9 TABL~ 18 Crop: Cotton (variety~ ~C - 510) Type of soil: Loam Sowing^ ~ebruary 28, 1989 Treatment: June 27, 1989 Evaluation: Plant damage July 6, 1989 Height of growth July 26, 1989 Substance g/ha of Plant Height o~ grow~h ac~ivQ damage cmDifference from ingredient % control [cm]
Control 0 0 g6.6 B 30 0 88.7 - 7.g D 10 6 96.6 0 B ~ D 30 ~ 5 3 a4 . 1- 12 ~ 5 B ~ D 30 ~ 10 6 83.4 - 13.2 B -~ D 30 ~ 20 8 80.8 - 15.8 EXAML~LES 19 TO 25 In tha ca~e of baxlsy, oat~, wheat and cotton, it wa~ al~o possible to reduce the height of growth, reduca lodging and increa3e the yield by mixturQs of substances :~ Y'1 - 30 - O.Z. 0050/41834 B ~ E.
TABLE lg Crop~ Summer wheat (variety: Ralle) Type of soil: Clay Sowing: March 20, 1989 Treatment: May 19, 1989 Evaluation: Plant damage June 2, 1989 Height of growth June 13, 1989 Sub~tance g/ha of Plant Height of grow*h active damage cmDiffer~nce from ingredient % control [cm]
Contxol 0 0 80.6 B 690 0 66.0- 14.5 E 10 a 8~oO+ 1.4 B ~ E690 ~ 5 9 60.0- 20.6 ; B + E690 * 10 0 57.023.6 690 + ~0 5 54.0~ 26.6 TA~LE 20 -~ 20 Crop: Winter wheat ~variQtys Xanzler) ~ype of soil: Clay Sowing: ~ctober 4, 1989 : Treatment: April 5, 1990 E~aluation: Plant damage June 5, 1990 Height of growth June 5; 1990 Sub~tanc~ g/ha of Plant Haight of gr~wt;h active damage cm Di~ference frvm inyredient % control [cm]
Control 0 0 122.9 B 690 0 117.2 - 5.7 E 5 0 122.8 - 0.1 B + ~ 690 + 1.25 0 113.2 - 9.7 B + ~ 690 t 2.5 0 114.8 ~ 8.1 B ~ 90 t 5 0 113.4 - 9.5 , - '' ~ ' :
~ ~ .
- 31 - O.Z. 005~/4183 Crop: Winter wheat (variety: Kraka) Type of soil: Loamy sand 50wing: November 7, 1989 Treatment: May 2, 1990 Evaluation: Plant damage June 5, 1990 Height of growth June 5, 1990 Substa~ce g/ha o~ Plant Height of grow*h active damage cm Difference fro~
lD ingredient % con~rol ~cm]
Control a 0 97.9 B 690 0 88.7 - 9.2 E 5 0 ~9.1 ~ 1.2 B ~ E 690 ~ 2.5 0 86.0 - 11,.9 B ~ E 690 -t 5 0 85.4 12.5 TAB~E 22 Crop: Oats (variety. Fl~mingsnova) Type of soil: Sandy lo~m Sowing. March R, 1990 Trea~ment: May 131 1990 : Evaluation: Plant damage June 8, 1990 . Height of growth June 8~ 1990 ; Sub~tance g/ha of Plant Height of growth active damage cm DifferQnce from ingredient % control [cm]
Control0 0 97.5 B 690 0 91.9 - 5.6 E 5 0 95.8 ~ 1.7 B + E690 + 5 0 89.1 - 8.4 - 32 - O. Z . 0050/41834 Crop: Summer barley ( variety: Gimpel ) I~ype of soil: Clay Sowing: March 20~ 1989 Treatment: May 18, 19 8 9 Evall~ation~ Plant damage June 2, 1989 Height of growth June 12, 1989 Lodging J uly 2 4, 1 9 8 9 Substance g/ha of Plant Height of Lodging/
active damage growt:h/ dif feren~e ingredient % difference from con f rom control trol [ % ]
[cm]
Control 0 0 95 . 4 38 B 690 0 94 . 4 - 1. 0 49 ~ 11 E 10 0 93.1 - 2.3 42 +4 E~ ~ E 690 ~ 10 0 91. 6 -3 . 8 36 - 2 B ~ E ~9û ~ 20 6 67 . 5 -27 . 9 0 - 38 2 û TAB~l~ 2 4 Crop s Cottoll ( variety: S~ - 2 ) Type of ~oil: Sandy loam Sowing : Fe~ruary 2 4, 1 9 8 9 I'reatment o June 2 7, 19 8 9 . ~ 25 Evaluation: Plant dsmage July 6, 198~
HQight of growth October 5, 1989 Sub~tance g/ha of Plant Height of grow~h ac:tive damage cm Di~erence from ing-redient % control ~cm]
3 0 ~
Control 0 0 125 . 0 B 30 0 116.2 8.8 2 130 . 0 + 5 . 0 B -1 E 30 + 5 0 111. 2 13 . 8 3S B ~ E 30 ~ 10 ~ 111. 2 -13 . 8 ~ 1 - 33 -O.Z. 0050/41~34 Crop~ Cot~on (variety: GC - 510) Type of soil: Loam Sowing~ February 28, l9B9 Treatment: June 27, 1989 Evaluation: Plant damage June 6~ 1990 Yield of seed cotton June 6, 1990 Sub~tance g/ha of PlantYield of seed co~ton active damagekg/ha Difference ~rom ingredient ~ control (kg/ha) :
Con~rol 0 0 3233 B 30 0 3375 + 142 30 + 5 ~ 3~53 + 22~
B + E 30 ~ 10 4 4003 ~ 770 B ~ E 30 + 20 3 2693 ~ 540
Claims (11)
1. A plant growth regulator containing a synergistic mixture of one or more growth regulating quaternary ammonium salts from the group consisting of the compounds I, comprising N,N-dimethylazacycloheptanium salts, N,N-dimethylpiperidinium salts, N,N-dimethyltetrahydro-pyridazinium salts, N,N,N-trimethyl-N-2-chloroethyl-ammonium salts, N-methylpyridinium salts and N,N-dime-thylpyrrolidinium salts, and an imidazolinyl derivative of the general formula II
II
where R1 is C1-C4-alkyl, R2 is C1-C4-alkyl or C3-C6-cyclo alkyl, R3 is hydrogen, hydroxyl, C1-C12-alkyl, C1-Cl2-alkoxy, C1-C12-alkylamino, di-C1-C12-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of tha following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, R4 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio and R5 and R6 independently of one another are each one of the groups stated for R4 or together form a 1,3-butadiene 1,4-diyl group which may carry from one to four halogen atoms and/or from one to three of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4 alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
II
where R1 is C1-C4-alkyl, R2 is C1-C4-alkyl or C3-C6-cyclo alkyl, R3 is hydrogen, hydroxyl, C1-C12-alkyl, C1-Cl2-alkoxy, C1-C12-alkylamino, di-C1-C12-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of tha following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, R4 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio and R5 and R6 independently of one another are each one of the groups stated for R4 or together form a 1,3-butadiene 1,4-diyl group which may carry from one to four halogen atoms and/or from one to three of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4 alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
2. A plant growth regulator as claimed in claim 1, containing one or more growth-regulating quaternary ammonium salts from the group consisting of the compounds I, comprising N,N-dimethylpiperidinium salts and N,N,N-trimethyl-N-2-chloroethylammonium salts.
3. A plant growth regulator as claimed in claim 1, - 35 - 0.Z. 0050/41834 containing an imidazolinyl derivative of the formula II
as claimed in claim 1, where R1, R2, R4, R5 and R6 have the meanings stated in claim 1 and R3 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino or di-C1-C8-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of the following groups:
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
as claimed in claim 1, where R1, R2, R4, R5 and R6 have the meanings stated in claim 1 and R3 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino or di-C1-C8-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of the following groups:
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
4. A plant growth regulator as claimed in claim 1, containing a synergistic mixture of one or more growth-regulating quaternary ammonium salts from the group consisting of the compounds I, comprising N,N-dimethyl-piperidinium salts and N,N,N-trimethyl-N-2-chloroethyl-ammonium salts and an imidazolinyl derivative of the formula II as claimed in claim 1, where R1 and R2 have the meanings stated in claim 1 and R3 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino or di-C1-C8-alkylamino or is phenyl, phenoxy or phenylamino, where the aromatic radicals may carry from one to five halogen atoms and/or from one to three of the following groups:
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, R4 is hydrogen or halogen and R5 and R6 independently of one another are each hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy; C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, or together form a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atoms and/or one of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, R4 is hydrogen or halogen and R5 and R6 independently of one another are each hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy; C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, or together form a 1,3-butadiene-1,4-diyl group which may carry from one to four halogen atoms and/or one of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio, and inert additives.
5. An agent as claimed in claim 4, containing a synergistic mixture of N,N-dimethylpiperidinium chloride, N,N,N-trimethyl-N-2-chloroethylamnonium chloride and 5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-nicotinecarboxylic acid.
- 36 - O.Z. 0050/41834
- 36 - O.Z. 0050/41834
6. A plant growth regulator as claimed in claim 1, containing a synergistic mixture of N,N-dimethyl-piperidinium chloride and 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid and inert additives.
7. A plant growth regulator as claimed in claim 1, containing a synergistic mixture of N,N-dimethyl-piperidinium chloride and isopropylammonium 2-(4-isoprop-yl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-nicotinecarbox-ylate and inert additives.
8. A plant growth regulator as claimed in claim 1, centaining a synergistic mixture of N,N-dimethyl-piperidinium chloride and 5-ethyl-2-(4-isopropyl-4-methyl 5-oxo-2 imidazolin-2-yl)-3-nicotinecarboxylic acid and inert additives.
9. An agent as claimed in claim 1 or 2 or 3 or 4 or 5 or 6 or 7 or 8, wherein tha weight ratio of ammonium salt I to imidazoline derivative II is from 0.1 : 1 to 1000 : 1.
10. A method for regulating plant growth, wherein the plants, their habitat or their seeds is or are treated with an amount, having a regulating effect, of a syner-gistic mixture as claimed in claim 1 or 2 or 3 or 4 or 5 or 6 or 7 or 8 or 9.
11. A method as claimed in claim 10, wherein the plants are cereals or cotton.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4026530A DE4026530A1 (en) | 1990-08-22 | 1990-08-22 | SYNERGISTIC AGENTS FOR REGULATING PLANT GROWTH |
| DEP4026530.7 | 1990-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2048275A1 true CA2048275A1 (en) | 1992-02-23 |
Family
ID=6412682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002048275A Abandoned CA2048275A1 (en) | 1990-08-22 | 1991-08-01 | Synergistic agents for regulating plant growth |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0472091B1 (en) |
| JP (1) | JPH05124915A (en) |
| KR (1) | KR920003857A (en) |
| CN (1) | CN1059633A (en) |
| AU (1) | AU8260891A (en) |
| CA (1) | CA2048275A1 (en) |
| CS (1) | CS248891A3 (en) |
| DE (2) | DE4026530A1 (en) |
| DK (1) | DK0472091T3 (en) |
| ES (1) | ES2064833T3 (en) |
| HU (1) | HU206433B (en) |
| PL (1) | PL167128B1 (en) |
| RU (1) | RU2050136C1 (en) |
| UA (1) | UA26391A (en) |
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| JP2001158702A (en) * | 1999-09-21 | 2001-06-12 | Fuji Kagaku Kk | Drug-carrying materials |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| CN1332606C (en) * | 2003-09-19 | 2007-08-22 | 沈阳化工研究院 | Photo stable herbicide |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| MX2007000095A (en) | 2004-06-24 | 2007-03-21 | Vertex Pharma | TRANSPORTER MODULATORS WITH UNION CASSETTE WITH ATP. |
| EP3219705B1 (en) | 2005-12-28 | 2020-03-11 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of the amorphous form of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| MX2011006833A (en) * | 2009-01-07 | 2011-08-03 | Basf Se | Pesticidal mixtures. |
| JP5763046B2 (en) | 2009-03-20 | 2015-08-12 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Method for producing modulators of cystic fibrosis membrane conductance regulators |
| US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| HK1203840A1 (en) | 2012-02-27 | 2015-11-06 | 沃泰克斯药物股份有限公司 | Pharmaceutical composition and administration thereof |
| JP6746569B2 (en) | 2014-10-07 | 2020-08-26 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795534A (en) * | 1972-02-18 | 1973-08-16 | Basf Ag | AGENTS FOR REGULATING PLANT GROWTH, CONTAINING NITROGEN SALT AS ACTIVE INGREDIENT |
| US4509973A (en) * | 1984-01-13 | 1985-04-09 | American Cyanamid Company | Plant growth regulating compositions |
| ZA86707B (en) * | 1985-02-04 | 1986-09-24 | American Cyanamid Co | Turfgrass management compositions |
-
1990
- 1990-08-22 DE DE4026530A patent/DE4026530A1/en not_active Withdrawn
-
1991
- 1991-08-01 CA CA002048275A patent/CA2048275A1/en not_active Abandoned
- 1991-08-12 CS CS912488A patent/CS248891A3/en unknown
- 1991-08-13 DK DK91113554.9T patent/DK0472091T3/en active
- 1991-08-13 ES ES91113554T patent/ES2064833T3/en not_active Expired - Lifetime
- 1991-08-13 DE DE59103571T patent/DE59103571D1/en not_active Expired - Lifetime
- 1991-08-13 EP EP91113554A patent/EP0472091B1/en not_active Expired - Lifetime
- 1991-08-19 JP JP3206675A patent/JPH05124915A/en not_active Withdrawn
- 1991-08-21 UA UA5001325A patent/UA26391A/en unknown
- 1991-08-21 RU SU915001325A patent/RU2050136C1/en not_active IP Right Cessation
- 1991-08-21 HU HU912757A patent/HU206433B/en not_active IP Right Cessation
- 1991-08-21 AU AU82608/91A patent/AU8260891A/en not_active Abandoned
- 1991-08-21 PL PL91291484A patent/PL167128B1/en not_active IP Right Cessation
- 1991-08-21 KR KR1019910014399A patent/KR920003857A/en not_active Ceased
- 1991-08-22 CN CN91105922A patent/CN1059633A/en active Pending
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| Publication number | Publication date |
|---|---|
| AU8260891A (en) | 1992-02-27 |
| PL291484A1 (en) | 1992-08-10 |
| JPH05124915A (en) | 1993-05-21 |
| CS248891A3 (en) | 1992-03-18 |
| HU912757D0 (en) | 1992-01-28 |
| EP0472091A1 (en) | 1992-02-26 |
| DE59103571D1 (en) | 1995-01-05 |
| KR920003857A (en) | 1992-03-27 |
| HUT58462A (en) | 1992-03-30 |
| DK0472091T3 (en) | 1995-03-13 |
| DE4026530A1 (en) | 1992-02-27 |
| HU206433B (en) | 1992-11-30 |
| ES2064833T3 (en) | 1995-02-01 |
| UA26391A (en) | 1999-08-30 |
| EP0472091B1 (en) | 1994-11-23 |
| PL167128B1 (en) | 1995-07-31 |
| CN1059633A (en) | 1992-03-25 |
| RU2050136C1 (en) | 1995-12-20 |
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