UA68435C2

UA68435C2 - Substituted benzoyl ketones and their use as herbicides

Substituted benzoyl ketones and their use as herbicides Download PDF

Info

Publication number: UA68435C2
Authority: UA; Ukraine
Prior art keywords: optionally substituted; carbon atoms; chlorine; methoxy; fluorine
Prior art date: 1999-05-08

Application number

UA2001128417A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Bayer Ag

Priority date

1999-05-08

Filing date

2000-04-26

Publication date

2004-08-16

2000-04-26 Application filed by Bayer Ag filed Critical Bayer Ag

2004-08-16 Publication of UA68435C2 publication Critical patent/UA68435C2/uk

Links

RXVBJUZEFSAYPW-UHFFFAOYSA-N 1,3-diphenylpropane-1,2,3-trione Chemical class C=1C=CC=CC=1C(=O)C(=O)C(=O)C1=CC=CC=C1 RXVBJUZEFSAYPW-UHFFFAOYSA-N 0.000 title claims abstract description 11
239000004009 herbicide Substances 0.000 title claims abstract description 7
-1 cyano, carbamoyl Chemical group 0.000 claims abstract description 346
229910052736 halogen Inorganic materials 0.000 claims abstract description 49
150000002367 halogens Chemical group 0.000 claims abstract description 49
239000001257 hydrogen Substances 0.000 claims abstract description 43
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 23
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 20
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 18
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 14
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 12
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
125000005842 heteroatom Chemical group 0.000 claims abstract description 4
229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
125000000464 thioxo group Chemical group S=* 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 22
125000004043 oxo group Chemical group O=* 0.000 claims abstract 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 73
125000004432 carbon atom Chemical group C* 0.000 claims description 71
239000000460 chlorine Substances 0.000 claims description 56
229910052801 chlorine Inorganic materials 0.000 claims description 56
125000001153 fluoro group Chemical group F* 0.000 claims description 48
229910052731 fluorine Inorganic materials 0.000 claims description 46
239000011737 fluorine Substances 0.000 claims description 46
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 36
150000001875 compounds Chemical class 0.000 claims description 34
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 30
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 27
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 25
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 22
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 15
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
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 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 5
125000005920 sec-butoxy group Chemical group 0.000 claims description 5
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000005605 benzo group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
125000006001 difluoroethyl group Chemical group 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
230000002363 herbicidal effect Effects 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 3
125000006606 n-butoxy group Chemical group 0.000 claims description 3
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000006323 alkenyl amino group Chemical group 0.000 claims description 2
125000005108 alkenylthio group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 2
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 2
125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
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 2
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
125000006003 dichloroethyl group Chemical group 0.000 claims description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
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125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
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