JPH0353282B2 - - Google Patents
Info
- Publication number
- JPH0353282B2 JPH0353282B2 JP2245869A JP24586990A JPH0353282B2 JP H0353282 B2 JPH0353282 B2 JP H0353282B2 JP 2245869 A JP2245869 A JP 2245869A JP 24586990 A JP24586990 A JP 24586990A JP H0353282 B2 JPH0353282 B2 JP H0353282B2
- Authority
- JP
- Japan
- Prior art keywords
- plant growth
- isonicotinic acid
- general formula
- formula
- compound
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 maleic acid hydrazide choline salt Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000005648 plant growth regulator Substances 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000004381 Choline salt Substances 0.000 claims 1
- 235000019417 choline salt Nutrition 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 244000025254 Cannabis sativa Species 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000209094 Oryza Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 241000209504 Poaceae Species 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000009422 growth inhibiting effect Effects 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002373 plant growth inhibitor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- FCTZHFATVFONMW-UHFFFAOYSA-N n-phenylpyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC1=CC=CC=C1 FCTZHFATVFONMW-UHFFFAOYSA-N 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- OXLXSOPFNVKUMU-UHFFFAOYSA-N 1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical class CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC OXLXSOPFNVKUMU-UHFFFAOYSA-N 0.000 description 1
- VLRWWADMWHAHFZ-UHFFFAOYSA-N 2-benzyl-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1CC1=CC=CC=C1 VLRWWADMWHAHFZ-UHFFFAOYSA-N 0.000 description 1
- UEIZUEWXLJOVLD-UHFFFAOYSA-N 3-(1-methylpyrrolidin-3-yl)pyridine Chemical compound C1N(C)CCC1C1=CC=CN=C1 UEIZUEWXLJOVLD-UHFFFAOYSA-N 0.000 description 1
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000743339 Agrostis Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000893384 Ceratorhiza oryzae-sativae Species 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- 206010013883 Dwarfism Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 241000209049 Poa pratensis Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- ZPUSFOHQVMOPOT-UHFFFAOYSA-N [5-chloro-2-(methylamino)phenyl]-phenylmethanol Chemical compound CNC1=CC=C(Cl)C=C1C(O)C1=CC=CC=C1 ZPUSFOHQVMOPOT-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- YTSACTNRGUJEGO-UHFFFAOYSA-N oxirane prop-1-ene Chemical group CC=C.C1CO1 YTSACTNRGUJEGO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、一般式[]
(式中R1は水素原子または炭素数1〜4の低級
アルキル基を示し、R2は水素原子または水酸基
を示し、Xはハロゲン原子または炭素数1〜2の
低級アルキル基を示し、nは0から2の整数を示
し、Zは水素原子またはハロゲン原子を示す。)
で表わされる化合物の1種または2種以上と、マ
レイン酸ヒドラジド・コリン酸(以下「C−
MH」)もしくは(2−クロルエチル)トリメチ
ルアンモニウムクロライド(以下「CCC」)との
混合物を有効成分として含有する植物生長調整剤
に関するもので、とくにイネ科植物の芝生、イネ
などを有効に矮化させることを目的としており、
適用範囲が広く、実用価値の高い植物生育抑制剤
を提供するものである。
上記一般式[]で表わされるイソニコチン酸
アニリド系加工物は、植物の生育抑制剤として、
例えばイネに対しては箱育苗および苗代での徒長
防止、老化防止、移植水田の倒伏防止などに巾広
く活用することができる。作用としては、あらゆ
る草種に対して有効であるが、とくにイネ科の植
物に対して高い生育抑制効果を発現する。有効な
植物としては、上記のイネをはじめムギ類、トウ
モロコシ、シバ類などが例としてあげられるが、
広葉植物にも安定した効果を発現する。
一方、C−MHならびにCCCは、植物生長調節
剤として公知の物質であり、すでに芝生の生育抑
制、イネ倒伏防止剤、花卉矮化剤として有用な薬
剤であるが、単用では効果がおとり、また高薬量
では有用植物の葉の褐変化させたり、新葉の発育
を遅らし美観を損つたりする欠点がある。
本発明者らは、これらの問題点を補足する目的
で種々研究の結果、上記一般式[]に示される
イソニコチン酸アニリド系化合物と上記公知の生
長調節剤とを組合せ、植物に処理することによ
り、有用植物に全く害を与えず、すぐれた生長調
節効果をあげることを見出した。すなわち、相加
的効果により、とくにイネ科の植物の芝、イネに
対し強い生育抑制作用を示し、処理時期が拡大し
たうえに意外にも相乗的効果の発現が認められ
た。すなわち、これらの化合物は各単剤で使用す
る場合よりもいちじるしく植物生育抑制力が増大
して、たとえばサツチ層が完成している芝生など
に対しても強力な生育抑制作用を示し、イネの倒
伏防止剤として出穂前いかなる処理時期において
も全く減収はみられない。
本発明は、上記のごとくイソニコチン酸アニリ
ド系化合物[]にC−MHもしくはCCCなどの
植物生長調節剤を配合してなる植物生長抑制剤お
よび倒伏防止剤に関するもので、有効成分の配合
にもとづく相乗的効果により、植物生長調節剤と
しての性能をいちじるしく改善したことを特徴と
するものである。本発明の混合に用いられた上記
の各植物生長調節剤は、植物生長調節剤もしくは
除草剤として、公知の植物生理活性物質である
が、一般式[]で表わされる化合物と配合し植
物生長調節剤の相乗効果の発現は新規である。な
お、上記以外の公知の植物生長調整剤と本発明に
用いられるイソニコチン酸アニリド系化合物との
混用による植物生長調節作用も検討したが、ほと
んどの組合わせで有用性がみられた。しかし、上
記薬剤との組合わせはもつとも実用価値の高いも
のであつた。
一般式[]で表わされる本発明化合物は新規
であり、以下に示す方法により製造することがで
きる。
(1) 一般式[]
(式中Yはハロゲン原子を示す。)で表わされ
るイソニコチン酸ハライドを適当な溶媒中、一
般式[]
(式中R1、R2、X、nおよびZは前記と同一
の意味を示す。)で表わされるアニリン誘導体
とを反応させて一般式[]で表わされる化合
物を製造する。この場合、適当な脱酸剤を用い
ると反応はより円滑に進行する。また、適当な
溶媒としては、ピリジン、メタノール、ベンゼ
ン、トルエン、キシレン、ジクロロメタン、ク
ロロホルム、テトラヒドロフラン、ジオキサ
ン、アセトン、ジメチルホルムアミド等があげ
られる。脱酸剤としてはピリジン、トリエチル
アミン、カ性ソーダ、カ性カリ、炭酸ソーダ、
炭酸カリ等があげられる。反応温度は室温にお
いても進行するが場合によつては冷却あるいは
加熱して行つてもよい。好ましくは0〜60℃が
よい。反応時間は条件の選定にもよるが、1か
ら8時間で完結する。反応終了後、常法により
分離・精製することにより目的物を得ることが
できる。
(2) 一般式[]
(式中R1、X、nおよびZは前記と同一の意
味を示す。)で表わされるイソニコチン酸誘導
体を適当な還元剤で還元することにより容易に
一般式[]で表わされる化合物を製造するこ
とができる。還元剤としては例えば水酸化リチ
ウムアルミニウム、水酸化ホウ素ナトリウム等
があげられる。実施に際しては各還元剤の常用
方法を用いることにより容易に製造することが
できる。
以下に製造例をあげて説明する。
製造例 1
N−メチル−イソニコチン酸−{4−クロロ−
2−(α−ヒドロキシベンジル)}アニリド(化
合物番号3)
2−メチルアミノ−5−クロロベンツヒドロー
ル15gをピリジン30mlに溶解し、この溶液を撹拌
しながら氷で冷却し、イソニコチン酸クロリド塩
酸塩1.4gを少量ずつ加える。この間約30分を必
要とする。更に3時間室温で撹拌した後、この反
応液に水200mlを加えると結晶が折出した。この
結晶を集めメタノール−アセトン混合溶媒から再
結晶するとN−メチル−イソニコチン酸−{4−
クロロ−2−(α−ヒドロキシベンジル)}アニリ
ド1.7gを得る。融点199〜201℃
元素分析値:C20H17ClN2O2(分子量351.81とし
て)
C H N
計算値(%) 68.08 4.86 7.94
実測値(%) 67.96 4.98 7.79
なお、溶媒をピリジンに換えてベンゼン、トル
エン、キシレン、ジクロロメタン、クロロホル
ム、テトラヒドロフラン、ジオキサン、アセト
ン、ジメチルホルムアミドを用いても目的物を得
た。
製造例 2
イソニコチン酸−{4−クロロ−2−(α−ヒド
ロキシベンジル)}アリニド(化合物番号4)
イソニコチン酸−(4−クロロ−2−ベンゾイ
ル)アニリド1.9gをメタノール20mlに溶解した
溶液に撹拌下水素化ホウ素ナトリウム0.2gを少
量ずつ加える。この間約30分を要す。更に室温で
2時間撹拌を続けた。反応終了後、水200mlを加
えると結晶が析出した。この結晶を濾取し、ジメ
チルホルムアミド−メタノール混合溶媒より再結
晶するとイソニコチン酸−{4−クロロ−2−(α
−ヒドロキシベンジル)アリニド1.8gを得る。
融点210〜212℃。
元素分析値:C19H15ClN2O2(分子量338.79とし
て)
C H N
計算値(%) 67.36 4.46 8.27
実測値(%) 67.18 4.56 8.29
なお、溶媒をメタノールに換えてピリジン、ベ
ンゼン、トルエン、キシレン、ジクロロメタン、
クロロホルム、テトラヒドロフラン、ジオキサ
ン、アセトン、ジメチルホルムアミドを用いて目
的物を得た。
製造例 3
イソニコチン酸−(4−クロロ−2−ベンジル)
アニリド(化合物番号1)
4−クロロ−2−ベンジルアニリン1.3gをピ
リジン30mlに溶解し、その溶液を氷で冷却し撹拌
下、イソニコチン酸クロリド塩酸塩1.4gを少量
ずつ加える。この間30分を要する。更に室温で3
時間撹拌を続け反応を完結させる。この反応溶液
に水200ml加えると結晶が折出した。この結晶を
集めエタノールで再結晶するとイソニコチン酸−
(4−クロロ−2−ベンジル)アニリド1.6gを得
る。融点178〜179℃
元素分析値:C19H15ClN2O2(分子量322.79とし
て)
C H N
計算値(%) 70.70 4.68 8.68
実測値(%) 70.75 4.79 8.65
次に、このようにして得られた一般式[]で
表わされる化合物の代表例を第1表に示す。本発
明はこられ例示化合物のみに限定されるものでは
ない。なお、化合物番号は以下の実施例および実
験例においても参照される。
The present invention is based on the general formula [] (In the formula, R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R 2 represents a hydrogen atom or a hydroxyl group, X represents a halogen atom or a lower alkyl group having 1 to 2 carbon atoms, and n represents Indicates an integer from 0 to 2, and Z indicates a hydrogen atom or a halogen atom.)
One or more compounds represented by and maleic acid hydrazide cholic acid (hereinafter "C-
This relates to a plant growth regulator that contains as an active ingredient a mixture with (2-chloroethyl)trimethylammonium chloride (MH) or (2-chloroethyl)trimethylammonium chloride (hereinafter referred to as "CCC"), and it particularly effectively dwarfs grasses of the grass family, such as lawns and rice. The purpose is to
The present invention provides a plant growth inhibitor with a wide range of applications and high practical value. The isonicotinic acid anilide-based processed product represented by the above general formula [] is used as a plant growth inhibitor.
For example, for rice, it can be widely used for raising seedlings in boxes, preventing the growth of seedlings, preventing aging, and preventing lodging of transplanted paddy fields. Although it is effective against all types of grass, it exhibits a particularly strong growth-inhibiting effect on plants belonging to the Poaceae family. Examples of effective plants include the rice mentioned above, as well as wheat, corn, and grass.
It also exhibits stable effects on broad-leaved plants. On the other hand, C-MH and CCC are substances known as plant growth regulators, and are already useful as lawn growth inhibitors, rice lodging prevention agents, and flower dwarfing agents, but they are not effective when used alone. In addition, high dosages have the disadvantage of causing the leaves of useful plants to turn brown, slowing the growth of new leaves, and impairing their aesthetic appearance. As a result of various studies to address these problems, the present inventors have found that the isonicotinic acid anilide compound represented by the above general formula [] and the above-mentioned known growth regulator are combined and treated with plants. It was discovered that this method does not cause any harm to useful plants and has an excellent growth regulating effect. In other words, due to the additive effect, it exhibited a strong growth-inhibiting effect particularly on grass and rice plants of the grass family, and in addition to extending the treatment period, unexpectedly, a synergistic effect was observed. In other words, these compounds significantly increase the ability to inhibit plant growth compared to when used alone, and exhibit a strong growth inhibiting effect even on lawns where the satsubishi layer has been completed, and inhibit lodging of rice. As an inhibitor, no decrease in yield was observed at any time of treatment before heading. The present invention relates to a plant growth inhibitor and a lodging prevention agent which are obtained by blending a plant growth regulator such as C-MH or CCC with an isonicotinic acid anilide compound as described above, and are based on the blending of active ingredients. It is characterized by significantly improved performance as a plant growth regulator due to synergistic effects. Each of the above-mentioned plant growth regulators used in the mixture of the present invention is a known plant physiologically active substance as a plant growth regulator or herbicide. The development of synergistic effects of agents is novel. The plant growth regulating effect of the mixed use of known plant growth regulators other than those mentioned above and the isonicotinic acid anilide compound used in the present invention was also investigated, and most of the combinations were found to be useful. However, the combination with the above drugs was of high practical value. The compound of the present invention represented by the general formula [ ] is novel and can be produced by the method shown below. (1) General formula [] (In the formula, Y represents a halogen atom.) Isonicotinic acid halide represented by the general formula [] (In the formula, R 1 , R 2 , X, n and Z have the same meanings as above.) A compound represented by the general formula [] is produced by reacting with the aniline derivative represented by the formula []. In this case, the reaction will proceed more smoothly if a suitable deoxidizing agent is used. Suitable solvents include pyridine, methanol, benzene, toluene, xylene, dichloromethane, chloroform, tetrahydrofuran, dioxane, acetone, dimethylformamide, and the like. As a deoxidizing agent, pyridine, triethylamine, caustic soda, caustic potash, soda carbonate,
Examples include potassium carbonate. The reaction may proceed at room temperature, but may be carried out with cooling or heating as the case may be. The temperature is preferably 0 to 60°C. Although the reaction time depends on the selection of conditions, it is completed in 1 to 8 hours. After the reaction is completed, the desired product can be obtained by separation and purification using conventional methods. (2) General formula [] (In the formula, R 1 , X, n and Z have the same meanings as above.) By reducing the isonicotinic acid derivative represented by the formula with an appropriate reducing agent, the compound represented by the general formula [ ] can be easily produced. can do. Examples of the reducing agent include lithium aluminum hydroxide and sodium borohydroxide. In practice, it can be easily produced by using a conventional method for each reducing agent. A manufacturing example will be given and explained below. Production example 1 N-methyl-isonicotinic acid-{4-chloro-
2-(α-Hydroxybenzyl)}anilide (Compound No. 3) Dissolve 15 g of 2-methylamino-5-chlorobenzhydrol in 30 ml of pyridine, cool the solution with ice while stirring, and dissolve isonicotinic acid chloride hydrochloride. Add 1.4g of salt little by little. This requires approximately 30 minutes. After further stirring at room temperature for 3 hours, 200 ml of water was added to the reaction solution, and crystals were precipitated. When these crystals were collected and recrystallized from a methanol-acetone mixed solvent, N-methyl-isonicotinic acid-{4-
1.7 g of chloro-2-(α-hydroxybenzyl)}anilide is obtained. Melting point 199-201℃ Elemental analysis value: C20H17ClN2O2 (molecular weight 351.81) C H N Calculated value (%) 68.08 4.86 7.94 Actual value (%) 67.96 4.98 7.79 In addition, by changing the solvent to pyridine, benzene, toluene, xylene, dichloromethane, The desired product was also obtained using chloroform, tetrahydrofuran, dioxane, acetone, and dimethylformamide. Production Example 2 Isonicotinic acid-{4-chloro-2-(α-hydroxybenzyl)}alinide (Compound No. 4) A solution of 1.9 g of isonicotinic acid-(4-chloro-2-benzoyl)anilide dissolved in 20 ml of methanol. Add 0.2 g of sodium borohydride little by little while stirring. This will take approximately 30 minutes. Stirring was continued for an additional 2 hours at room temperature. After the reaction was completed, 200 ml of water was added to precipitate crystals. The crystals were collected by filtration and recrystallized from a dimethylformamide-methanol mixed solvent to give isonicotinic acid-{4-chloro-2-(α
1.8 g of -hydroxybenzyl)alinide are obtained.
Melting point 210-212℃. Elemental analysis value: C19H15ClN2O2 (as molecular weight 338.79) C H N Calculated value (%) 67.36 4.46 8.27 Actual value (%) 67.18 4.56 8.29 In addition, the solvent was changed to methanol and pyridine, benzene, toluene, xylene, dichloromethane,
The desired product was obtained using chloroform, tetrahydrofuran, dioxane, acetone, and dimethylformamide. Production example 3 Isonicotinic acid-(4-chloro-2-benzyl)
Anilide (Compound No. 1) Dissolve 1.3 g of 4-chloro-2-benzylaniline in 30 ml of pyridine, cool the solution with ice, and add 1.4 g of isonicotinyl chloride hydrochloride little by little while stirring. This will take 30 minutes. Further at room temperature 3
Continue stirring for an hour to complete the reaction. When 200 ml of water was added to this reaction solution, crystals were precipitated. When these crystals are collected and recrystallized with ethanol, isonicotinic acid-
1.6 g of (4-chloro-2-benzyl)anilide are obtained. Melting point 178-179℃ Elemental analysis value: C19H15ClN2O2 (molecular weight 322.79) C H N Calculated value (%) 70.70 4.68 8.68 Actual value (%) 70.75 4.79 8.65 Next, it is expressed by the general formula [] obtained in this way. Table 1 shows representative examples of the compounds. The present invention is not limited to these exemplified compounds. Note that the compound numbers are also referred to in the following Examples and Experimental Examples.
【表】【table】
【表】【table】
【表】【table】
【表】
本発明の植物生長調節剤は、前記一般式[]
で示される化合物の1種または2種以上と前記各
植物生長調節剤との混合物を10アール当り通常
100〜3000g、好ましくは150〜2000gの割合で使
用するのが適当であるが、植物の栽培条件、生育
状況、種類により適宜に薬量を調節し得ることは
いうまでもない。例えば、茎葉処理するときは10
アール当り150〜2000gが適当であり、育苗箱
(30cm×60cm×3cm)に処理するときは10アール
当り(20箱)2〜150gの割合で使用する。
また、製剤化に当つては、一般の農薬の調剤に
用いられる個体、液体の各種担体と混合して、水
和剤、乳剤、粒剤等に製造することができる。さ
らに薬剤に分散剤、希釈剤、乳化剤、浸透剤、粘
結剤等の補助剤を添加してもよい。また、使用目
的に応じて上記構成成分を他の殺草剤、殺菌剤、
殺虫剤、植物生長調節剤、肥料などと併用するこ
とができる。
ここにいう担体とは個体、液体のいづれでもよ
い。これらの例を列記すればタルク、クレー、カ
リオン、珪藻土、炭酸カルシウム、木粉、澱粉、
アラビアゴム、水、アルコール、ケロシン、ナフ
サ、キシロール、キシレン、シクロヘキサノン、
メチルナフタレン、ベンゼン、アセトン等があ
り、さらに薬剤の製剤上使用される補助剤、例え
ば展着剤、乳化剤、分散剤、湿展剤等として非イ
オン系(ポリオキシエチレンアルキルフエニール
エーテル、エチレンオキシドプロピレンオキシド
共重合体、リグニンスルホン酸塩、ソルビタンエ
ステル類等)、アニオン系(石けん類、硫酸化油
類、アルキル硫酸エステル塩類、石油スルホネー
ト類、ジオクチルスルホサクシネート塩類、アル
キルアリールスルホン酸塩類等)カチオン系(脂
肪族アミン塩類、第四級アンモニウム塩類、アル
キルピリジニウム塩類等)および両性系(アルキ
ルアミノエチルグリシン、アルキルジメチルベタ
イン、ポリグリコール硫酸エステル、アルキルア
ミンスルホン酸等)の界面活性剤などがあげられ
る。
但し、本発明の実施態様は必ずしも上述の剤型
に限定されるものではないということはいうまで
もない。
また、製剤化に当り、混合割合は一般式[]
で表わされる化合物5〜45%:前記植物生長調節
剤1〜25%:界面活性剤0〜15%:担体30〜94%
が最適である。なお、剤型によつては界面活性剤
を添加しなくともよい。
また、本発明においては各種殺虫剤、殺菌剤、
除草剤、植物生長調節剤、殺ダニ剤、殺線虫剤、
誘引剤、忌避剤、植物栄養剤、肥料等と混用する
ことにより、より広範囲の効果を期待することも
できる。
本発明薬剤を使用する時期としては、例えば播
種期、幼苗期、生長期いずれの時期でもよく、ま
た対象植物によつて例えば地上散布、水面または
土壌、浸漬等の処理をすることができる。
次に実験例を示して本発明の効果を詳細に説明
する。
実験例 1
1/5000アールのプラスチツクポツトに砂壌土を
つめ、ケンタツキーブルーグラスを播種し、3年
間慣行法により育成した芝生を草丈0.5cmに刈取
つたのち、後記実施例1に示される製剤化法で水
和剤となし(イソニコチン酸性アニリド系化合
物、C−MHおよびCCC単用の場合も同様に製剤
化し、クレーを増減して組成分中の有効成分濃度
を一定にした。)たものを、所定薬量となるよう
に100/10aの割合で、水で希釈し処理した。
以後はガラス温室内で調査日まで管理した。効果
の調査は、薬剤処理後30日目に芝の草丈を測定す
ると同時に、地上部0.5cmを残し刈取り、その生
体重を測定した。
その結果は第2表に示すとおりである。[Table] The plant growth regulator of the present invention has the general formula []
A mixture of one or more of the compounds represented by the above and each of the above plant growth regulators is usually added per 10 ares.
It is appropriate to use it at a rate of 100 to 3000 g, preferably 150 to 2000 g, but it goes without saying that the amount can be adjusted as appropriate depending on the cultivation conditions, growth status, and type of the plant. For example, when processing foliage, 10
150 to 2000 g per are is appropriate, and when processing into seedling boxes (30 cm x 60 cm x 3 cm), use at a rate of 2 to 150 g per 10 are (20 boxes). In addition, for formulation, it can be mixed with various solid and liquid carriers used in the formulation of general agricultural chemicals to produce wettable powders, emulsions, granules, etc. Furthermore, auxiliary agents such as dispersants, diluents, emulsifiers, penetrants, and binders may be added to the drug. In addition, depending on the purpose of use, the above components may be combined with other herbicides, fungicides,
It can be used in combination with insecticides, plant growth regulators, fertilizers, etc. The carrier herein may be either solid or liquid. Examples of these include talc, clay, carrion, diatomaceous earth, calcium carbonate, wood flour, starch,
Gum arabic, water, alcohol, kerosene, naphtha, xylol, xylene, cyclohexanone,
These include methylnaphthalene, benzene, acetone, etc., and nonionic agents (polyoxyethylene alkyl phenyl ether, ethylene oxide propylene, (oxide copolymers, lignin sulfonates, sorbitan esters, etc.), anionic (soaps, sulfated oils, alkyl sulfate ester salts, petroleum sulfonates, dioctyl sulfosuccinate salts, alkylaryl sulfonates, etc.) cations Examples include surfactants of type (aliphatic amine salts, quaternary ammonium salts, alkylpyridinium salts, etc.) and amphoteric type (alkylaminoethylglycine, alkyldimethylbetaine, polyglycol sulfate, alkylamine sulfonic acid, etc.). . However, it goes without saying that the embodiments of the present invention are not necessarily limited to the above-mentioned dosage form. In addition, when formulating, the mixing ratio is determined by the general formula []
5-45% of the compound represented by: 1-25% of the plant growth regulator: 0-15% of the surfactant: 30-94% of the carrier
is optimal. Note that depending on the dosage form, it is not necessary to add a surfactant. In addition, in the present invention, various insecticides, fungicides,
Herbicides, plant growth regulators, acaricides, nematicides,
By using it in combination with attractants, repellents, plant nutrients, fertilizers, etc., a wider range of effects can be expected. The chemical of the present invention may be used during, for example, the sowing period, the seedling period, or the growing period, and depending on the target plant, treatments such as spraying on the ground, water surface or soil, and immersion can be performed. Next, the effects of the present invention will be explained in detail by showing experimental examples. Experimental Example 1 A 1/5000 are plastic pot was filled with sandy loam soil, Kentucky bluegrass was sown, and the grass was cultivated using a conventional method for 3 years. After mowing the grass to a height of 0.5 cm, the formulation shown in Example 1 below was prepared. (Isonicotine acid anilide compounds, C-MH and CCC alone were formulated in the same way, and the concentration of active ingredient in the composition was kept constant by increasing or decreasing the amount of clay.) was diluted with water at a ratio of 100/10a to give the prescribed dose.
Thereafter, they were kept in a glass greenhouse until the day of the survey. To investigate the effect, the height of the grass was measured 30 days after the chemical treatment, and at the same time, the grass was cut leaving 0.5 cm above ground, and its fresh weight was measured. The results are shown in Table 2.
【表】【table】
【表】
実験例 2
ベントグラス養成しているゴルフ場のグリーン
(5年間育成)1区2m×2mに区切り、地上部
を0.5cmの高さに刈取つたのち、後記実施例2に
示される製剤化法で乳剤となし(イソニコチン酸
アニリド系化合物、C−MHおよびCCC単用の場
合も同様に製剤化しキシレンを増減して、組織分
中の有効成分濃度を一定にした。)たものを所定
量となるように水で希釈して、茎葉部に十分付着
するように小型ふんむ器を用いて100/10aの
割合で散布した。効果の調査は、薬剤処理後30日
目に芝の草丈および地上部の生体重(草丈0.5cm
に刈取つたもの)を測定した。
その結果は第3表に示すとおりである。[Table] Experimental Example 2 A green at a golf course where bentgrass is cultivated (grown for 5 years). After dividing the green into 2 m x 2 m sections and cutting the above-ground part to a height of 0.5 cm, the formulation shown in Example 2 below was prepared. (In the case of single use of isonicotinic acid anilide compounds, C-MH and CCC, formulations were made in the same way, and the amount of xylene was increased or decreased to keep the concentration of the active ingredient in the tissue constant.) It was diluted with water to a certain amount and sprayed at a ratio of 100/10a using a small dung bowl to ensure sufficient adhesion to the stems and leaves. The effect was investigated on the 30th day after treatment with the grass plant height and the fresh weight of the aboveground part (plant height 0.5cm).
The amount of ivy harvested was measured. The results are shown in Table 3.
【表】
実験例 3
水田で稚苗イネ(品種:コシヒカリ)を慣行法
により機械移植し、(昭和56年5月20日)、出穂42
日前に、1区10cm2に区切り、後記実施例3に示さ
れる製剤化法で粒剤となし(イソニコチン酸アニ
リド系化合物CCC単用の場合も同様に製剤化し、
ベントナイトを増減して組成分中の有効成分濃度
を一定にした。)たものを、所定量手まき処理し
た。以後は水深を3〜5cmに保つた。効果の調査
は8月30日に稈長を、また10月10日に倒伏の程度
を調査した。
その結果は第4表に示すとおりである。[Table] Experimental example 3 Young rice seedlings (variety: Koshihikari) were mechanically transplanted in a paddy field using the conventional method (May 20, 1980), and the ears appeared at 42
1 day in advance, divided into 10 cm 2 sections, and prepared into granules according to the formulation method shown in Example 3 below (in the case of isonicotinic acid anilide compound CCC alone, it was formulated in the same way,
The active ingredient concentration in the composition was kept constant by increasing or decreasing bentonite. ) was manually sown in a predetermined amount. After that, the water depth was kept at 3 to 5 cm. To investigate the effects, culm length was investigated on August 30th, and the degree of lodging was investigated on October 10th. The results are shown in Table 4.
【表】
つぎに、本発明の実施例を示すが、化合物、担
体および使用割合は本実施例に限定されるもので
はない。
実施例 1
化合物No.4 40重量部
C−MH 20 〃
アルキル硫酸ソーダ 5 〃
クレー 35 〃
これらを均一になるまでよく混合し、微粉砕し
て水和剤を得る。これを使用時に所定濃度に希釈
して散布する。
実施例 2
化合物No.1 20重量部
CCC 5 〃
ポリオキシエチレンフエニルエーテル 7 〃
アルキルベンゼンスルフオン酸カルシウム
3 〃
キシレン 40 〃
シクロヘキサノン 25 〃
これらを均一になるまでよく混合溶解して乳剤
を得る。これを使用時に水で所定濃度に希釈して
散布する。
実施例 3
化合物No.5 10重量部
C−MH 1.5 〃
ベントナイト 53 〃
ケイソウ土 35.5 〃
これらを均一になるまで混合し、微粉砕して常
法により造粒し、粒剤として用いる。[Table] Examples of the present invention are shown below, but the compounds, carriers, and proportions used are not limited to these examples. Example 1 Compound No. 4 40 parts by weight C-MH 20 Sodium alkyl sulfate 5 Clay 35 These are thoroughly mixed until homogeneous and pulverized to obtain a wettable powder. When used, this is diluted to a predetermined concentration and sprayed. Example 2 Compound No. 1 20 parts by weight CCC 5 Polyoxyethylene phenyl ether 7 Calcium alkylbenzenesulfonate
3. xylene 40. cyclohexanone 25. Mix and dissolve these ingredients thoroughly until uniform to obtain an emulsion. When using this, dilute it with water to a predetermined concentration and spray. Example 3 Compound No. 5 10 parts by weight C-MH 1.5 Bentonite 53 Diatomaceous earth 35.5 These are mixed until homogeneous, pulverized and granulated by a conventional method, and used as granules.
Claims (1)
し、R2は水素原子または水酸基を示し、Xはハ
ロゲン原子または低級アルキル基を示し、nは0
から2の整数を示し、Zは水素原子またはハロゲ
ン原子を示す。)で表わされる化合物の1種また
は2種以上と、マレイン酸ヒドラジド・コリン塩
もしくは(2−クロルエチル)トリメチルアンモ
ニウムクロライドとの混合物を有効成分として含
有することを特徴とする植物生長調節剤。[Claims] 1. General formula (In the formula, R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a hydrogen atom or a hydroxyl group, X represents a halogen atom or a lower alkyl group, and n is 0
represents an integer from 2 to 2, and Z represents a hydrogen atom or a halogen atom. 1. A plant growth regulator comprising, as an active ingredient, a mixture of one or more of the compounds represented by formula (1) and maleic acid hydrazide choline salt or (2-chloroethyl)trimethylammonium chloride.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2245869A JPH03123706A (en) | 1982-03-26 | 1990-09-14 | Plant growth-modulating agent |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4711282A JPS58164501A (en) | 1982-03-26 | 1982-03-26 | Plant growth regulator |
JP2245869A JPH03123706A (en) | 1982-03-26 | 1990-09-14 | Plant growth-modulating agent |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4711282A Division JPS58164501A (en) | 1982-03-26 | 1982-03-26 | Plant growth regulator |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH03123706A JPH03123706A (en) | 1991-05-27 |
JPH0353282B2 true JPH0353282B2 (en) | 1991-08-14 |
Family
ID=26387264
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2245869A Granted JPH03123706A (en) | 1982-03-26 | 1990-09-14 | Plant growth-modulating agent |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03123706A (en) |
-
1990
- 1990-09-14 JP JP2245869A patent/JPH03123706A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPH03123706A (en) | 1991-05-27 |
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