DE2550519A1 - Chlorsubstituierte vinylamino-benzoesaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren - Google Patents
Chlorsubstituierte vinylamino-benzoesaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatorenInfo
- Publication number
- DE2550519A1 DE2550519A1 DE19752550519 DE2550519A DE2550519A1 DE 2550519 A1 DE2550519 A1 DE 2550519A1 DE 19752550519 DE19752550519 DE 19752550519 DE 2550519 A DE2550519 A DE 2550519A DE 2550519 A1 DE2550519 A1 DE 2550519A1
- Authority
- DE
- Germany
- Prior art keywords
- benzoic acid
- vinylamino
- methylcarbonyl
- carb
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 CHLORINE-SUBSTITUTED VINYLAMINO-BENZOIC ACID Chemical class 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000005648 plant growth regulator Substances 0.000 title description 3
- 239000000460 chlorine Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000008635 plant growth Effects 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 73
- UDEWPOVQBGFNGE-UHFFFAOYSA-N propyl benzoate Chemical compound CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 45
- 239000005711 Benzoic acid Substances 0.000 description 41
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 35
- 241000196324 Embryophyta Species 0.000 description 32
- 235000010233 benzoic acid Nutrition 0.000 description 31
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 30
- 239000004480 active ingredient Substances 0.000 description 27
- 239000003630 growth substance Substances 0.000 description 22
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 description 21
- 239000000126 substance Substances 0.000 description 13
- 230000012010 growth Effects 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 9
- SDIDYFBTIZOPLA-UHFFFAOYSA-N n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1 SDIDYFBTIZOPLA-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920001577 copolymer Chemical group 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 7
- 238000003306 harvesting Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 5
- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000009105 vegetative growth Effects 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- TWHKXHIVJVVGCC-UHFFFAOYSA-N 2-(ethenylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC=C TWHKXHIVJVVGCC-UHFFFAOYSA-N 0.000 description 2
- ITTXGKOHFZJUEX-UHFFFAOYSA-N 3-(ethoxymethylidene)pentane-2,4-dione Chemical compound CCOC=C(C(C)=O)C(C)=O ITTXGKOHFZJUEX-UHFFFAOYSA-N 0.000 description 2
- DMVLRZKLCLWWOP-UHFFFAOYSA-N 3-amino-2,5,6-trichlorobenzoic acid Chemical compound NC1=CC(Cl)=C(Cl)C(C(O)=O)=C1Cl DMVLRZKLCLWWOP-UHFFFAOYSA-N 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 206010053759 Growth retardation Diseases 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000005417 aminobenzoic acid derivatives Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 239000002270 dispersing agent Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- KTMGNAIGXYODKQ-VOTSOKGWSA-N ethyl (e)-2-cyano-3-ethoxyprop-2-enoate Chemical compound CCO\C=C(/C#N)C(=O)OCC KTMGNAIGXYODKQ-VOTSOKGWSA-N 0.000 description 2
- QKYICUQIRABKBD-UHFFFAOYSA-N ethyl 3-amino-2,5,6-trichlorobenzoate Chemical compound CCOC(=O)C1=C(Cl)C(N)=CC(Cl)=C1Cl QKYICUQIRABKBD-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 231100000001 growth retardation Toxicity 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940035339 tri-chlor Drugs 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- XUVFMGLRHXUGOW-UHFFFAOYSA-N 2-[3-(3,5-dimethylphenyl)anilino]benzoic acid Chemical compound CC1=CC(C)=CC(C=2C=C(NC=3C(=CC=CC=3)C(O)=O)C=CC=2)=C1 XUVFMGLRHXUGOW-UHFFFAOYSA-N 0.000 description 1
- UKTXDHXWPVMVLT-UHFFFAOYSA-N 2-amino-3-ethenylbenzoic acid Chemical class NC1=C(C=C)C=CC=C1C(O)=O UKTXDHXWPVMVLT-UHFFFAOYSA-N 0.000 description 1
- KXRAZNSPJYPEPL-UHFFFAOYSA-N 2-chloro-n-ethyl-3-[(3-oxo-2-propanoylpent-1-enyl)amino]benzamide Chemical compound CCNC(=O)C1=CC=CC(NC=C(C(=O)CC)C(=O)CC)=C1Cl KXRAZNSPJYPEPL-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical group C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 description 1
- TZWYCVZYVVGIEE-UHFFFAOYSA-N 3-amino-2,5,6-trichloro-n-ethylbenzamide Chemical compound CCNC(=O)C1=C(Cl)C(N)=CC(Cl)=C1Cl TZWYCVZYVVGIEE-UHFFFAOYSA-N 0.000 description 1
- PDBDIHXWUWYQOQ-UHFFFAOYSA-N 3-amino-2-chloro-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC(N)=C1Cl PDBDIHXWUWYQOQ-UHFFFAOYSA-N 0.000 description 1
- SWDQXKDACCQUOX-UHFFFAOYSA-N 3-amino-2-chloro-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(N)=C1Cl SWDQXKDACCQUOX-UHFFFAOYSA-N 0.000 description 1
- IQMIVFNEHPKEAI-UHFFFAOYSA-N 3-amino-2-chlorobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1Cl IQMIVFNEHPKEAI-UHFFFAOYSA-N 0.000 description 1
- ZKMZEPUPFKWLAY-UHFFFAOYSA-N 3-amino-5-chloro-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC(N)=CC(Cl)=C1 ZKMZEPUPFKWLAY-UHFFFAOYSA-N 0.000 description 1
- NOSLVNSUYGRJEV-UHFFFAOYSA-N 3-amino-5-chloro-n-methylbenzamide Chemical compound CNC(=O)C1=CC(N)=CC(Cl)=C1 NOSLVNSUYGRJEV-UHFFFAOYSA-N 0.000 description 1
- ATFAXWNNFCBZNY-UHFFFAOYSA-N 3-amino-5-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1 ATFAXWNNFCBZNY-UHFFFAOYSA-N 0.000 description 1
- UHAIXOAIWKXYOM-UHFFFAOYSA-N 4-(ethoxymethylidene)heptane-3,5-dione Chemical compound CCOC=C(C(=O)CC)C(=O)CC UHAIXOAIWKXYOM-UHFFFAOYSA-N 0.000 description 1
- SNADPAABQFQPQY-UHFFFAOYSA-N 4-(methoxymethylidene)heptane-3,5-dione Chemical compound CCC(=O)C(=COC)C(=O)CC SNADPAABQFQPQY-UHFFFAOYSA-N 0.000 description 1
- LFHQNZZBMYGKDG-UHFFFAOYSA-N 5-amino-2,3-dichloro-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC(N)=CC(Cl)=C1Cl LFHQNZZBMYGKDG-UHFFFAOYSA-N 0.000 description 1
- RYCVUGZLAQJJLC-UHFFFAOYSA-N 5-amino-2,3-dichlorobenzoic acid Chemical compound NC1=CC(Cl)=C(Cl)C(C(O)=O)=C1 RYCVUGZLAQJJLC-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- IUNZAJLJPWYERS-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)[O-].C(=C)[NH3+] Chemical compound C(C1=CC=CC=C1)(=O)[O-].C(=C)[NH3+] IUNZAJLJPWYERS-UHFFFAOYSA-N 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- MDCVBTQNWMLXRL-UHFFFAOYSA-N dimethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OC)C(=O)OC MDCVBTQNWMLXRL-UHFFFAOYSA-N 0.000 description 1
- GMLPEMUZDOQOLM-UHFFFAOYSA-N dimethyl 2-[[2-chloro-3-(ethylcarbamoyl)anilino]methylidene]propanedioate Chemical compound CCNC(=O)C1=CC=CC(NC=C(C(=O)OC)C(=O)OC)=C1Cl GMLPEMUZDOQOLM-UHFFFAOYSA-N 0.000 description 1
- 230000005059 dormancy Effects 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FNASCUBBFNCFQO-UHFFFAOYSA-N ethyl 2-(ethoxymethylidene)-3-oxobutanoate Chemical compound CCOC=C(C(C)=O)C(=O)OCC FNASCUBBFNCFQO-UHFFFAOYSA-N 0.000 description 1
- LECIVGGFOMFFFQ-UHFFFAOYSA-N ethyl 2-(ethoxymethylidene)-3-oxohexanoate Chemical compound CCCC(=O)C(=COCC)C(=O)OCC LECIVGGFOMFFFQ-UHFFFAOYSA-N 0.000 description 1
- QXPMTJPDLMLQDR-UHFFFAOYSA-N ethyl 2-(ethoxymethylidene)-3-oxopentanoate Chemical compound CCOC=C(C(=O)CC)C(=O)OCC QXPMTJPDLMLQDR-UHFFFAOYSA-N 0.000 description 1
- QBQOFGAGRMJUSR-UHFFFAOYSA-N ethyl 2-(ethoxymethylidene)-4-methyl-3-oxopentanoate Chemical compound CCOC=C(C(=O)C(C)C)C(=O)OCC QBQOFGAGRMJUSR-UHFFFAOYSA-N 0.000 description 1
- ZSRKOWVRLFEESG-UHFFFAOYSA-N ethyl 2-(methoxymethylidene)-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=COC ZSRKOWVRLFEESG-UHFFFAOYSA-N 0.000 description 1
- ZIBOPIBWCSTXFW-UHFFFAOYSA-N ethyl 2-(methoxymethylidene)-3-oxohexanoate Chemical compound CCCC(=O)C(=COC)C(=O)OCC ZIBOPIBWCSTXFW-UHFFFAOYSA-N 0.000 description 1
- IJMYNUOLRBBTNJ-UHFFFAOYSA-N ethyl 2-(methoxymethylidene)-4-methyl-3-oxopentanoate Chemical compound CCOC(=O)C(=COC)C(=O)C(C)C IJMYNUOLRBBTNJ-UHFFFAOYSA-N 0.000 description 1
- KAFVHDPIBCRLNV-UHFFFAOYSA-N ethyl 2-cyano-3-methoxyprop-2-enoate Chemical compound CCOC(=O)C(C#N)=COC KAFVHDPIBCRLNV-UHFFFAOYSA-N 0.000 description 1
- MHMMVAMMASEGOB-UHFFFAOYSA-N ethyl 3-amino-2,5-dichlorobenzoate Chemical compound CCOC(=O)C1=CC(Cl)=CC(N)=C1Cl MHMMVAMMASEGOB-UHFFFAOYSA-N 0.000 description 1
- PQYZWIXJWWAFSD-UHFFFAOYSA-N ethyl 3-amino-2-chlorobenzoate Chemical compound CCOC(=O)C1=CC=CC(N)=C1Cl PQYZWIXJWWAFSD-UHFFFAOYSA-N 0.000 description 1
- QZZLHCKPHMTUMA-UHFFFAOYSA-N ethyl 3-amino-5-chlorobenzoate Chemical compound CCOC(=O)C1=CC(N)=CC(Cl)=C1 QZZLHCKPHMTUMA-UHFFFAOYSA-N 0.000 description 1
- OCIKLPYZWXOECD-UHFFFAOYSA-N ethyl 5-amino-2,3-dichlorobenzoate Chemical compound CCOC(=O)C1=CC(N)=CC(Cl)=C1Cl OCIKLPYZWXOECD-UHFFFAOYSA-N 0.000 description 1
- OCMMZRKNONEJAO-UHFFFAOYSA-N ethyl 5-amino-2-chlorobenzoate Chemical compound CCOC(=O)C1=CC(N)=CC=C1Cl OCMMZRKNONEJAO-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 230000002015 leaf growth Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- FYXVHJJZGRTONS-AATRIKPKSA-N methyl (e)-2-cyano-3-ethoxyprop-2-enoate Chemical compound CCO\C=C(/C#N)C(=O)OC FYXVHJJZGRTONS-AATRIKPKSA-N 0.000 description 1
- AGNUFSNBWSLFIN-SNAWJCMRSA-N methyl (e)-2-cyano-3-methoxyprop-2-enoate Chemical compound CO\C=C(/C#N)C(=O)OC AGNUFSNBWSLFIN-SNAWJCMRSA-N 0.000 description 1
- YNIBFTZCNSFNRK-UHFFFAOYSA-N methyl 2-(ethoxymethylidene)-3-oxobutanoate Chemical compound CCOC=C(C(C)=O)C(=O)OC YNIBFTZCNSFNRK-UHFFFAOYSA-N 0.000 description 1
- HWPCTYUHWMMMCM-UHFFFAOYSA-N methyl 2-(ethoxymethylidene)-3-oxohexanoate Chemical compound CCCC(=O)C(C(=O)OC)=COCC HWPCTYUHWMMMCM-UHFFFAOYSA-N 0.000 description 1
- OBMYJJVUKJJCKB-UHFFFAOYSA-N methyl 2-(ethoxymethylidene)-3-oxopentanoate Chemical compound CCOC=C(C(=O)CC)C(=O)OC OBMYJJVUKJJCKB-UHFFFAOYSA-N 0.000 description 1
- DTOYXQOBUDDXHQ-UHFFFAOYSA-N methyl 2-(ethoxymethylidene)-4-methyl-3-oxopentanoate Chemical compound CCOC=C(C(=O)OC)C(=O)C(C)C DTOYXQOBUDDXHQ-UHFFFAOYSA-N 0.000 description 1
- RDEHDFHNQPTQFC-UHFFFAOYSA-N methyl 2-(methoxymethylidene)-3-oxobutanoate Chemical compound COC=C(C(C)=O)C(=O)OC RDEHDFHNQPTQFC-UHFFFAOYSA-N 0.000 description 1
- CTQUKAIPQLJNLV-UHFFFAOYSA-N methyl 2-(methoxymethylidene)-3-oxohexanoate Chemical compound CCCC(=O)C(=COC)C(=O)OC CTQUKAIPQLJNLV-UHFFFAOYSA-N 0.000 description 1
- AUNZMVTVNQSEAD-UHFFFAOYSA-N methyl 2-(methoxymethylidene)-3-oxopentanoate Chemical compound CCC(=O)C(=COC)C(=O)OC AUNZMVTVNQSEAD-UHFFFAOYSA-N 0.000 description 1
- KHLZAAQVTCSXRR-UHFFFAOYSA-N methyl 2-(methoxymethylidene)-4-methyl-3-oxopentanoate Chemical compound COC=C(C(=O)OC)C(=O)C(C)C KHLZAAQVTCSXRR-UHFFFAOYSA-N 0.000 description 1
- UUGXRETTWOVDSB-UHFFFAOYSA-N methyl 3-amino-2,5,6-trichlorobenzoate Chemical compound COC(=O)C1=C(Cl)C(N)=CC(Cl)=C1Cl UUGXRETTWOVDSB-UHFFFAOYSA-N 0.000 description 1
- DTSSCQVCVYZGSI-UHFFFAOYSA-N methyl 3-amino-2,5-dichlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC(N)=C1Cl DTSSCQVCVYZGSI-UHFFFAOYSA-N 0.000 description 1
- NKBQKMXNIWIFAE-UHFFFAOYSA-N methyl 3-amino-2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1Cl NKBQKMXNIWIFAE-UHFFFAOYSA-N 0.000 description 1
- ORKTXZHKYFWCRB-UHFFFAOYSA-N methyl 3-amino-5-chlorobenzoate Chemical compound COC(=O)C1=CC(N)=CC(Cl)=C1 ORKTXZHKYFWCRB-UHFFFAOYSA-N 0.000 description 1
- JEWUMKBIZFDWSI-UHFFFAOYSA-N methyl 5-amino-2,3-dichlorobenzoate Chemical compound COC(=O)C1=CC(N)=CC(Cl)=C1Cl JEWUMKBIZFDWSI-UHFFFAOYSA-N 0.000 description 1
- LBNPBOFVHYOPIB-UHFFFAOYSA-N methyl 5-amino-2-chlorobenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1Cl LBNPBOFVHYOPIB-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000017807 phytochemicals Nutrition 0.000 description 1
- 229930000223 plant secondary metabolite Natural products 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
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- 230000008092 positive effect Effects 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- FDPYRJOCNUAAOW-UHFFFAOYSA-N propan-2-yl 2-(ethoxymethylidene)-3-oxohexanoate Chemical compound CCCC(=O)C(=COCC)C(=O)OC(C)C FDPYRJOCNUAAOW-UHFFFAOYSA-N 0.000 description 1
- IQHRPCLJUDCIQV-UHFFFAOYSA-N propan-2-yl 2-(ethoxymethylidene)-3-oxopentanoate Chemical compound CCOC=C(C(=O)CC)C(=O)OC(C)C IQHRPCLJUDCIQV-UHFFFAOYSA-N 0.000 description 1
- MCUBASTYMDIXCR-UHFFFAOYSA-N propan-2-yl 2-(ethoxymethylidene)-4-methyl-3-oxopentanoate Chemical compound CCOC=C(C(=O)C(C)C)C(=O)OC(C)C MCUBASTYMDIXCR-UHFFFAOYSA-N 0.000 description 1
- KYSXTAKLEQSORX-UHFFFAOYSA-N propan-2-yl 2-(methoxymethylidene)-3-oxobutanoate Chemical compound COC=C(C(C)=O)C(=O)OC(C)C KYSXTAKLEQSORX-UHFFFAOYSA-N 0.000 description 1
- CSHFSHMFGLSIMV-UHFFFAOYSA-N propan-2-yl 2-(methoxymethylidene)-4-methyl-3-oxopentanoate Chemical compound COC=C(C(=O)C(C)C)C(=O)OC(C)C CSHFSHMFGLSIMV-UHFFFAOYSA-N 0.000 description 1
- WASPASIKNRXSOA-UHFFFAOYSA-N propan-2-yl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OC(C)C WASPASIKNRXSOA-UHFFFAOYSA-N 0.000 description 1
- VRFWVNXZVAPFJM-UHFFFAOYSA-N propan-2-yl 2-cyano-3-methoxyprop-2-enoate Chemical compound COC=C(C#N)C(=O)OC(C)C VRFWVNXZVAPFJM-UHFFFAOYSA-N 0.000 description 1
- MYEJJZBWYKUXPK-UHFFFAOYSA-N propan-2-yl 3-[(2-butanoyl-3-oxohex-1-enyl)amino]-2-chlorobenzoate Chemical compound CCCC(=O)C(C(=O)CCC)=CNC1=CC=CC(C(=O)OC(C)C)=C1Cl MYEJJZBWYKUXPK-UHFFFAOYSA-N 0.000 description 1
- ZHPBTCQBOJDLPP-UHFFFAOYSA-N propan-2-yl 3-amino-2,5,6-trichlorobenzoate Chemical compound CC(C)OC(=O)C1=C(Cl)C(N)=CC(Cl)=C1Cl ZHPBTCQBOJDLPP-UHFFFAOYSA-N 0.000 description 1
- FGQGWHAUIDWTCN-UHFFFAOYSA-N propan-2-yl 3-amino-5-chlorobenzoate Chemical compound CC(C)OC(=O)C1=CC(N)=CC(Cl)=C1 FGQGWHAUIDWTCN-UHFFFAOYSA-N 0.000 description 1
- UQUKUOYEIBJDNC-UHFFFAOYSA-N propan-2-yl 3-ethoxyprop-2-enoate Chemical compound CCOC=CC(=O)OC(C)C UQUKUOYEIBJDNC-UHFFFAOYSA-N 0.000 description 1
- DKJGZMYYDGBYDW-UHFFFAOYSA-N propan-2-yl 5-amino-2,3-dichlorobenzoate Chemical compound CC(C)OC(=O)C1=CC(N)=CC(Cl)=C1Cl DKJGZMYYDGBYDW-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ZUHKTCDJGGPGPW-UHFFFAOYSA-N propyl 2-(ethoxymethylidene)-3-oxobutanoate Chemical compound CCCOC(=O)C(C(C)=O)=COCC ZUHKTCDJGGPGPW-UHFFFAOYSA-N 0.000 description 1
- HHOYFRBHWJZFFY-UHFFFAOYSA-N propyl 2-(ethoxymethylidene)-3-oxohexanoate Chemical compound CCCOC(=O)C(=COCC)C(=O)CCC HHOYFRBHWJZFFY-UHFFFAOYSA-N 0.000 description 1
- ZLHBPYWESJQSPV-UHFFFAOYSA-N propyl 2-(ethoxymethylidene)-3-oxopentanoate Chemical compound CCCOC(=O)C(C(=O)CC)=COCC ZLHBPYWESJQSPV-UHFFFAOYSA-N 0.000 description 1
- KTLOTYJIZFPWQS-UHFFFAOYSA-N propyl 2-(methoxymethylidene)-3-oxobutanoate Chemical compound CCCOC(=O)C(C(C)=O)=COC KTLOTYJIZFPWQS-UHFFFAOYSA-N 0.000 description 1
- CKPGCWLRBHZNCM-UHFFFAOYSA-N propyl 2-(methoxymethylidene)-3-oxohexanoate Chemical compound CCCOC(=O)C(=COC)C(=O)CCC CKPGCWLRBHZNCM-UHFFFAOYSA-N 0.000 description 1
- NPPJVGDIXNVAJK-UHFFFAOYSA-N propyl 2-(methoxymethylidene)-3-oxopentanoate Chemical compound CCCOC(=O)C(=COC)C(=O)CC NPPJVGDIXNVAJK-UHFFFAOYSA-N 0.000 description 1
- ZSTNWIOSKZFISK-UHFFFAOYSA-N propyl 2-(methoxymethylidene)-4-methyl-3-oxopentanoate Chemical compound CCCOC(=O)C(=COC)C(=O)C(C)C ZSTNWIOSKZFISK-UHFFFAOYSA-N 0.000 description 1
- VOVBPIDTKDMXDO-UHFFFAOYSA-N propyl 2-chloro-3-[(3-oxo-2-propanoylpent-1-enyl)amino]benzoate Chemical compound CCCOC(=O)C1=CC=CC(NC=C(C(=O)CC)C(=O)CC)=C1Cl VOVBPIDTKDMXDO-UHFFFAOYSA-N 0.000 description 1
- FIFPZWYUHTYUFG-UHFFFAOYSA-N propyl 2-chloro-3-[[4-methyl-2-(2-methylpropanoyl)-3-oxopent-1-enyl]amino]benzoate Chemical compound CCCOC(=O)C1=CC=CC(NC=C(C(=O)C(C)C)C(=O)C(C)C)=C1Cl FIFPZWYUHTYUFG-UHFFFAOYSA-N 0.000 description 1
- VXAZRBJDBUUDMS-UHFFFAOYSA-N propyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCCOC(=O)C(C#N)=COCC VXAZRBJDBUUDMS-UHFFFAOYSA-N 0.000 description 1
- QFGRQFISOICWKG-UHFFFAOYSA-N propyl 2-cyano-3-methoxyprop-2-enoate Chemical compound CCCOC(=O)C(C#N)=COC QFGRQFISOICWKG-UHFFFAOYSA-N 0.000 description 1
- AMILNBHPKLBTSG-UHFFFAOYSA-N propyl 3-[(2-butanoyl-3-oxohex-1-enyl)amino]-2-chlorobenzoate Chemical compound CCCOC(=O)C1=CC=CC(NC=C(C(=O)CCC)C(=O)CCC)=C1Cl AMILNBHPKLBTSG-UHFFFAOYSA-N 0.000 description 1
- YLYVHGXJDNHEGW-UHFFFAOYSA-N propyl 3-amino-2,5,6-trichlorobenzoate Chemical compound CCCOC(=O)C1=C(Cl)C(N)=CC(Cl)=C1Cl YLYVHGXJDNHEGW-UHFFFAOYSA-N 0.000 description 1
- KFSZTCMZCNMPOK-UHFFFAOYSA-N propyl 3-amino-2,5-dichlorobenzoate Chemical compound CCCOC(=O)C1=CC(Cl)=CC(N)=C1Cl KFSZTCMZCNMPOK-UHFFFAOYSA-N 0.000 description 1
- AAGXRJRJXXKFHJ-UHFFFAOYSA-N propyl 3-amino-2-chlorobenzoate Chemical compound CCCOC(=O)C1=CC=CC(N)=C1Cl AAGXRJRJXXKFHJ-UHFFFAOYSA-N 0.000 description 1
- ZWQCVQMQURSSMJ-UHFFFAOYSA-N propyl 3-amino-5-chlorobenzoate Chemical compound CCCOC(=O)C1=CC(N)=CC(Cl)=C1 ZWQCVQMQURSSMJ-UHFFFAOYSA-N 0.000 description 1
- PXBLVMUBDYXSOE-UHFFFAOYSA-N propyl 5-amino-2,3-dichlorobenzoate Chemical compound CCCOC(=O)C1=CC(N)=CC(Cl)=C1Cl PXBLVMUBDYXSOE-UHFFFAOYSA-N 0.000 description 1
- BSBGRZNFZKZGAE-UHFFFAOYSA-N propyl 5-amino-2-chlorobenzoate Chemical compound CCCOC(=O)C1=CC(N)=CC=C1Cl BSBGRZNFZKZGAE-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752550519 DE2550519A1 (de) | 1975-11-11 | 1975-11-11 | Chlorsubstituierte vinylamino-benzoesaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren |
| US05/734,478 US4104049A (en) | 1975-11-11 | 1976-10-20 | Chlorine-substituted vinylaminobenzoic acid compounds and plant growth regulant compositions |
| AU19253/76A AU502168B2 (en) | 1975-11-11 | 1976-11-02 | Chlorine-substituted vinylaminobenzoic acid derivatives |
| PT65799A PT65799B (en) | 1975-11-11 | 1976-11-04 | Process for the preparation of chlorine-substituted vinylatminobenzoic acid derivatives and their use as plant-growth regulators |
| IL50862A IL50862A0 (en) | 1975-11-11 | 1976-11-08 | Chlorine-substituted vinylaminobenzoic acid derivatives their preparation and their use as plant-growth regulators |
| GB46370/76A GB1495240A (en) | 1975-11-11 | 1976-11-08 | Chlorine-substituted vinylaminobenzoic acid derivatives and their use as plant-growth regulators |
| TR18939A TR18939A (tr) | 1975-11-11 | 1976-11-08 | Klor-suebstituee vinilaminobenzoik asid tuerevleri,imallerine mahsus usul ve bitki bueyuemesi ayarlayicilari olarak kullanilmalari |
| NL7612443A NL7612443A (nl) | 1975-11-11 | 1976-11-09 | Met chloor gesubstitueerde vinylaminobenzoezuur- derivaten, werkwijze voor het bereiden ervan, alsmede toepassing ervan als regulatoren van de plantengroei. |
| AT831076A AT346376B (de) | 1975-11-11 | 1976-11-09 | Pflanzenwachstumsregulierendes mittel |
| DD7600195682A DD128279A5 (de) | 1975-11-11 | 1976-11-09 | Mittel zur beeinflussung des pflanzenwachstums |
| BE172190A BE848134A (fr) | 1975-11-11 | 1976-11-09 | Nouveaux derives d'acides vinylamino-benzoiques chlores, leur procede de preparation et leur application comme substances de croissance |
| ES453183A ES453183A1 (es) | 1975-11-11 | 1976-11-10 | Procedimiento para preparar derivados de acidos vinilamino- benzoicos cloro-sustituidos. |
| BR7607504A BR7607504A (pt) | 1975-11-11 | 1976-11-10 | Processo para a preparacao de derivados do acido vinil-aminobenzoico substituidos por cloro,e composicoes reguladoras do crescimento da planta |
| SE7612499A SE7612499L (sv) | 1975-11-11 | 1976-11-10 | Klorsubstituerade vinylaminobensoesyraderivat, sett att framstella desamma och deras anvendning som tillvextregulatorer for vexter |
| DK506376A DK506376A (da) | 1975-11-11 | 1976-11-10 | Chlorsubstituerede vinylaminobenzoesyrederivater fremgangsmade til deres fremstilling savel som deres anvendelse som plantevekstregulatorer |
| FR7633949A FR2331550A1 (fr) | 1975-11-11 | 1976-11-10 | Nouveaux derives d'acides vinylamino-benzoiques chlores, leur procede de preparation et leur application comme substances de croissance des vegetaux |
| ZA766750A ZA766750B (en) | 1975-11-11 | 1976-11-10 | Chlorine-substituted vinylaminobenzoic acid derivatives and their use as plantgrowth regulators |
| JP51134751A JPS5259129A (en) | 1975-11-11 | 1976-11-11 | Chlorine substituted vynyl amino benzoic acid derivatives and use of same as plant growth controling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752550519 DE2550519A1 (de) | 1975-11-11 | 1975-11-11 | Chlorsubstituierte vinylamino-benzoesaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2550519A1 true DE2550519A1 (de) | 1977-05-12 |
Family
ID=5961416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752550519 Pending DE2550519A1 (de) | 1975-11-11 | 1975-11-11 | Chlorsubstituierte vinylamino-benzoesaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4104049A (enExample) |
| JP (1) | JPS5259129A (enExample) |
| AT (1) | AT346376B (enExample) |
| AU (1) | AU502168B2 (enExample) |
| BE (1) | BE848134A (enExample) |
| BR (1) | BR7607504A (enExample) |
| DD (1) | DD128279A5 (enExample) |
| DE (1) | DE2550519A1 (enExample) |
| DK (1) | DK506376A (enExample) |
| ES (1) | ES453183A1 (enExample) |
| FR (1) | FR2331550A1 (enExample) |
| GB (1) | GB1495240A (enExample) |
| IL (1) | IL50862A0 (enExample) |
| NL (1) | NL7612443A (enExample) |
| PT (1) | PT65799B (enExample) |
| SE (1) | SE7612499L (enExample) |
| TR (1) | TR18939A (enExample) |
| ZA (1) | ZA766750B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8521082D0 (en) * | 1985-08-22 | 1985-09-25 | Ici Plc | Fungicides |
| GB9114369D0 (en) * | 1991-07-03 | 1991-08-21 | Kodak Ltd | Activated propenes as colour couplers and a method for their production |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL279734A (enExample) * | 1961-06-26 | |||
| DE1642231C3 (de) * | 1967-09-15 | 1981-06-04 | Basf Ag, 6700 Ludwigshafen | Herbizid auf Basis von Amino-cyanacrylsäureester-derivaten |
| US3981717A (en) * | 1969-09-24 | 1976-09-21 | American Cyanamid Company | Herbicidal methods |
| US3726662A (en) * | 1970-01-14 | 1973-04-10 | Monsanto Co | Herbicidal anilinomethylene-malononitriles |
-
1975
- 1975-11-11 DE DE19752550519 patent/DE2550519A1/de active Pending
-
1976
- 1976-10-20 US US05/734,478 patent/US4104049A/en not_active Expired - Lifetime
- 1976-11-02 AU AU19253/76A patent/AU502168B2/en not_active Expired
- 1976-11-04 PT PT65799A patent/PT65799B/pt unknown
- 1976-11-08 TR TR18939A patent/TR18939A/xx unknown
- 1976-11-08 IL IL50862A patent/IL50862A0/xx unknown
- 1976-11-08 GB GB46370/76A patent/GB1495240A/en not_active Expired
- 1976-11-09 AT AT831076A patent/AT346376B/de not_active IP Right Cessation
- 1976-11-09 DD DD7600195682A patent/DD128279A5/xx unknown
- 1976-11-09 NL NL7612443A patent/NL7612443A/xx not_active Application Discontinuation
- 1976-11-09 BE BE172190A patent/BE848134A/xx unknown
- 1976-11-10 FR FR7633949A patent/FR2331550A1/fr active Granted
- 1976-11-10 DK DK506376A patent/DK506376A/da unknown
- 1976-11-10 SE SE7612499A patent/SE7612499L/xx unknown
- 1976-11-10 ZA ZA766750A patent/ZA766750B/xx unknown
- 1976-11-10 ES ES453183A patent/ES453183A1/es not_active Expired
- 1976-11-10 BR BR7607504A patent/BR7607504A/pt unknown
- 1976-11-11 JP JP51134751A patent/JPS5259129A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU1925376A (en) | 1978-05-11 |
| JPS5259129A (en) | 1977-05-16 |
| DD128279A5 (de) | 1977-11-09 |
| AT346376B (de) | 1978-11-10 |
| SE7612499L (sv) | 1977-05-12 |
| US4104049A (en) | 1978-08-01 |
| ES453183A1 (es) | 1977-11-16 |
| ATA831076A (de) | 1978-03-15 |
| ZA766750B (en) | 1977-10-26 |
| BE848134A (fr) | 1977-05-09 |
| DK506376A (da) | 1977-05-12 |
| PT65799B (en) | 1978-05-12 |
| GB1495240A (en) | 1977-12-14 |
| FR2331550B1 (enExample) | 1980-09-12 |
| AU502168B2 (en) | 1979-07-12 |
| TR18939A (tr) | 1977-12-20 |
| NL7612443A (nl) | 1977-05-13 |
| IL50862A0 (en) | 1977-01-31 |
| PT65799A (en) | 1976-12-01 |
| FR2331550A1 (fr) | 1977-06-10 |
| BR7607504A (pt) | 1977-09-20 |
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| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |