UA75657C2 - Herbicidal substituted benzoylpyrazoles - Google Patents

Info

Publication number

UA75657C2

UA75657C2 UA20031211972A UA20031211972A UA75657C2 UA 75657 C2 UA75657 C2 UA 75657C2 UA 20031211972 A UA20031211972 A UA 20031211972A UA 20031211972 A UA20031211972 A UA 20031211972A UA 75657 C2 UA75657 C2 UA 75657C2

Authority

UA

Ukraine

Prior art keywords

substituted

necessary

cyano

fluorine

chlorine

Prior art date

2001-05-21

Links

• Espacenet
• Global Dossier
• Discuss

• 230000002363 herbicidal effect Effects 0.000 title claims description 7
• UYMQWGLCXYHTES-UHFFFAOYSA-N phenyl(1h-pyrazol-5-yl)methanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=NN1 UYMQWGLCXYHTES-UHFFFAOYSA-N 0.000 title abstract description 13
• 239000004009 herbicide Substances 0.000 claims abstract description 8
• -1 cyano, carbamoyl Chemical group 0.000 claims description 584
• 239000000460 chlorine Chemical group 0.000 claims description 102
• 229910052801 chlorine Inorganic materials 0.000 claims description 102
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 88
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 61
• 125000004432 carbon atom Chemical group C* 0.000 claims description 60
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
• 150000001875 compounds Chemical class 0.000 claims description 58
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 49
• 229910052794 bromium Chemical group 0.000 claims description 49
• 229910052731 fluorine Inorganic materials 0.000 claims description 46
• 239000011737 fluorine Substances 0.000 claims description 45
• 229910052736 halogen Inorganic materials 0.000 claims description 45
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 42
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 39
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 37
• 125000001153 fluoro group Chemical group F* 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 27
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 26
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 25
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000004414 alkyl thio group Chemical group 0.000 claims description 17
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 17
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 15
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 14
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 14
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 12
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 10
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 10
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 10
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 10
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• 125000005110 aryl thio group Chemical group 0.000 claims description 8
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 8
• 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 8
• 125000006437 ethyl cyclopropyl group Chemical group 0.000 claims description 8
• 125000002769 thiazolinyl group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 239000002904 solvent Substances 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 6
• 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 6
• 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 6
• 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 6
• 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims description 6
• 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 6
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 6
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000002541 furyl group Chemical class 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 6
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 6
• 125000005968 oxazolinyl group Chemical group 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 6
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 5
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
• 125000003971 isoxazolinyl group Chemical group 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 4
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 4
• 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 4
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
• 125000001769 aryl amino group Chemical group 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 4
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 3
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 3
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 3
• 125000005883 dithianyl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
• 239000011630 iodine Substances 0.000 claims description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
• 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 2
• 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 claims description 2
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
• 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 2
• 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 claims description 2
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
• 125000005981 pentynyl group Chemical group 0.000 claims description 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
• 125000006320 propynyl amino group Chemical group 0.000 claims description 2
• 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
• 125000000532 dioxanyl group Chemical group 0.000 claims 2
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
• 150000002221 fluorine Chemical class 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
• 125000003386 piperidinyl group Chemical group 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 38
• 238000004519 manufacturing process Methods 0.000 abstract description 3
• 239000000543 intermediate Substances 0.000 abstract description 2
• 241000196324 Embryophyta Species 0.000 description 84
• 239000013543 active substance Substances 0.000 description 39
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000000126 substance Substances 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000000203 mixture Substances 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• 240000008042 Zea mays Species 0.000 description 11
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
• 235000010233 benzoic acid Nutrition 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 239000003085 diluting agent Substances 0.000 description 10
• 229920000742 Cotton Polymers 0.000 description 9
• 241000219146 Gossypium Species 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
• 235000005822 corn Nutrition 0.000 description 9
• 108090000623 proteins and genes Proteins 0.000 description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• 235000010469 Glycine max Nutrition 0.000 description 7
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
• 150000001559 benzoic acids Chemical class 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• 150000004702 methyl esters Chemical class 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 239000002689 soil Substances 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 6
• 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 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
• 229910052796 boron Inorganic materials 0.000 description 6
• 230000003993 interaction Effects 0.000 description 6
• 230000009261 transgenic effect Effects 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
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• 235000013399 edible fruits Nutrition 0.000 description 5
• 239000008187 granular material Substances 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 235000002595 Solanum tuberosum Nutrition 0.000 description 4
• 244000061456 Solanum tuberosum Species 0.000 description 4
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• 239000002253 acid Substances 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 239000011591 potassium Substances 0.000 description 4
• 235000012015 potatoes Nutrition 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000005507 spraying Methods 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 239000005711 Benzoic acid Substances 0.000 description 3
• 240000002791 Brassica napus Species 0.000 description 3
• 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
• 241000132536 Cirsium Species 0.000 description 3
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
• UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
• 125000002877 alkyl aryl group Chemical group 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 125000002837 carbocyclic group Chemical group 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
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• 230000006378 damage Effects 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 230000012010 growth Effects 0.000 description 3
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