SK175797A3

SK175797A3 - Herbicidal ketals and spirocycles

Herbicidal ketals and spirocycles Download PDF

Info

Publication number: SK175797A3
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; alkyl; och; atom
Prior art date: 1995-06-29

Application number

SK1757-97A

Other languages

English (en)

Slovak (sk)

Inventor

Chi-Ping Tseng

Original Assignee

Du Pont

Priority date

1995-06-29

Filing date

1996-06-19

Publication date

1998-07-08

1996-06-19 Application filed by Du Pont filed Critical Du Pont

1998-07-08 Publication of SK175797A3 publication Critical patent/SK175797A3/sk

Links

230000002363 herbicidal effect Effects 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims abstract description 249
239000000203 mixture Substances 0.000 claims abstract description 126
229910052799 carbon Inorganic materials 0.000 claims abstract description 84
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 32
229910052736 halogen Inorganic materials 0.000 claims abstract description 30
150000002367 halogens Chemical class 0.000 claims abstract description 29
238000000034 method Methods 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 12
125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 8
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 79
-1 alkoxy carbon Chemical compound 0.000 claims description 60
229910052717 sulfur Inorganic materials 0.000 claims description 46
150000001721 carbon Chemical group 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 38
125000005843 halogen group Chemical group 0.000 claims description 33
229910052760 oxygen Inorganic materials 0.000 claims description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 22
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
125000004430 oxygen atom Chemical group O* 0.000 claims description 15
239000004094 surface-active agent Substances 0.000 claims description 15
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 11
239000003085 diluting agent Substances 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
125000004434 sulfur atom Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
230000012010 growth Effects 0.000 claims description 6
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 1
125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
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125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 2
239000000460 chlorine Substances 0.000 description 1008
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238000012360 testing method Methods 0.000 description 39
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
235000016854 Cyperus rotundus Nutrition 0.000 description 36
244000075634 Cyperus rotundus Species 0.000 description 36
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241000335053 Beta vulgaris Species 0.000 description 33
235000021533 Beta vulgaris Nutrition 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
241001289540 Fallopia convolvulus Species 0.000 description 31
238000002360 preparation method Methods 0.000 description 31
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239000000243 solution Substances 0.000 description 30
244000100545 Lolium multiflorum Species 0.000 description 29
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235000011684 Sorghum saccharatum Nutrition 0.000 description 27
238000002844 melting Methods 0.000 description 26
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239000000126 substance Substances 0.000 description 24
241000209200 Bromus Species 0.000 description 23
238000005481 NMR spectroscopy Methods 0.000 description 23
241001148727 Bromus tectorum Species 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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240000006394 Sorghum bicolor Species 0.000 description 20
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235000005490 Chenopodium botrys Nutrition 0.000 description 18
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241000234653 Cyperus Species 0.000 description 17
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240000003461 Setaria viridis Species 0.000 description 16
235000002248 Setaria viridis Nutrition 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
235000008131 Solanum ptycanthum Nutrition 0.000 description 15
240000002307 Solanum ptychanthum Species 0.000 description 15
239000003153 chemical reaction reagent Substances 0.000 description 15
241000169130 Heteranthera limosa Species 0.000 description 14
244000037751 Persicaria maculosa Species 0.000 description 14
235000004442 Polygonum persicaria Nutrition 0.000 description 14
239000002689 soil Substances 0.000 description 14
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239000002253 acid Substances 0.000 description 13
238000007796 conventional method Methods 0.000 description 13
238000009472 formulation Methods 0.000 description 13
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241000061675 Staria Species 0.000 description 12
239000012043 crude product Substances 0.000 description 12
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 12
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230000004044 response Effects 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
241000209117 Panicum Species 0.000 description 11
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 11
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 11
239000002585 base Substances 0.000 description 11
241000219144 Abutilon Species 0.000 description 10
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
241001303487 Digitaria <clam> Species 0.000 description 10
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241000207763 Solanum Species 0.000 description 10
235000012735 amaranth Nutrition 0.000 description 10
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
241000207892 Convolvulus Species 0.000 description 9
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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239000008187 granular material Substances 0.000 description 8
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 8
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BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 description 7
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XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 6
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