CA1281724C - Haloalkyltriazolinones - Google Patents

Haloalkyltriazolinones

Info

Publication number: CA1281724C
Authority: CA; Canada
Prior art keywords: carbon atoms; alkyl; compound; alkoxy; substituted
Prior art date: 1985-02-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000499759A

Other languages

English (en)

Inventor

Lester L. Maravetz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FMC Corp

Original Assignee

FMC Corp

Priority date (The priority date 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 date listed.)

1985-02-04

Filing date

1986-01-17

Publication date

1991-03-19

1986-01-17 Application filed by FMC Corp filed Critical FMC Corp

1991-03-19 Application granted granted Critical

1991-03-19 Publication of CA1281724C publication Critical patent/CA1281724C/fr

Status Expired legal-status Critical Current

Links

125000001188 haloalkyl group Chemical group 0.000 title claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 141
125000000217 alkyl group Chemical group 0.000 claims abstract description 65
230000002363 herbicidal effect Effects 0.000 claims abstract description 42
125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 73
239000000203 mixture Substances 0.000 claims description 46
125000003545 alkoxy group Chemical group 0.000 claims description 24
239000000460 chlorine Chemical group 0.000 claims description 19
229910052801 chlorine Inorganic materials 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 5
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000000262 haloalkenyl group Chemical group 0.000 claims description 5
125000000232 haloalkynyl group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
230000008635 plant growth Effects 0.000 claims description 2
-1 cyanomethoxy Chemical group 0.000 description 60
239000000243 solution Substances 0.000 description 24
239000007787 solid Substances 0.000 description 20
241000894007 species Species 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
241000196324 Embryophyta Species 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000009472 formulation Methods 0.000 description 14
239000012074 organic phase Substances 0.000 description 13
125000001424 substituent group Chemical group 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
125000003118 aryl group Chemical group 0.000 description 11
239000004009 herbicide Substances 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 10
150000005840 aryl radicals Chemical group 0.000 description 9
235000017168 chlorine Nutrition 0.000 description 9
229940060038 chlorine Drugs 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
150000002367 halogens Chemical class 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
239000002270 dispersing agent Substances 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
239000007788 liquid Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000006378 damage Effects 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
229940073584 methylene chloride Drugs 0.000 description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000002689 soil Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
235000005853 Cyperus esculentus Nutrition 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
240000007594 Oryza sativa Species 0.000 description 5
240000003461 Setaria viridis Species 0.000 description 5
235000002248 Setaria viridis Nutrition 0.000 description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
240000006995 Abutilon theophrasti Species 0.000 description 4
240000001505 Cyperus odoratus Species 0.000 description 4
240000002439 Sorghum halepense Species 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
208000014674 injury Diseases 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
229940093956 potassium carbonate Drugs 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
UBSYNSJYJZDOFC-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-5-(difluoromethyl)-4-methyl-1,2,4-triazol-3-one Chemical compound O=C1N(C)C(C(F)F)=NN1C1=CC(O)=C(Cl)C=C1F UBSYNSJYJZDOFC-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
241000219146 Gossypium Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
231100000674 Phytotoxicity Toxicity 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
235000010086 Setaria viridis var. viridis Nutrition 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
230000002950 deficient Effects 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
KQSKJPHNNJNLPT-UHFFFAOYSA-N ethyl n-(2,2-difluoroacetyl)carbamate Chemical compound CCOC(=O)NC(=O)C(F)F KQSKJPHNNJNLPT-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000002045 lasting effect Effects 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
229960005419 nitrogen Drugs 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
229940080818 propionamide Drugs 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011369 resultant mixture Substances 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
231100000167 toxic agent Toxicity 0.000 description 3
239000003440 toxic substance Substances 0.000 description 3
ATZUDJNXQGSYAW-UHFFFAOYSA-N (2,2-difluoroacetyl)carbamic acid Chemical compound OC(=O)NC(=O)C(F)F ATZUDJNXQGSYAW-UHFFFAOYSA-N 0.000 description 2
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 2
SFFUEHODRAXXIA-UHFFFAOYSA-N 2,2,2-trifluoroacetonitrile Chemical compound FC(F)(F)C#N SFFUEHODRAXXIA-UHFFFAOYSA-N 0.000 description 2
GPGFRXPNEWSGAW-UHFFFAOYSA-N 2-(2,4-dichloro-5-methoxyphenyl)-5-(difluoromethyl)-1h-1,2,4-triazol-3-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(N=C(N2)C(F)F)=O)=C1Cl GPGFRXPNEWSGAW-UHFFFAOYSA-N 0.000 description 2
YUXJUCJDZKGZMJ-UHFFFAOYSA-N 2-(2,4-dichloro-5-propan-2-yloxyphenyl)-5-(trifluoromethyl)-1h-1,2,4-triazol-3-one Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(N=C(N2)C(F)(F)F)=O)=C1Cl YUXJUCJDZKGZMJ-UHFFFAOYSA-N 0.000 description 2
NOVOKJHHCQHKCU-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-5-(difluoromethyl)-1h-1,2,4-triazol-3-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(N=C(N2)C(F)F)=O)=C1F NOVOKJHHCQHKCU-UHFFFAOYSA-N 0.000 description 2
AFAIUVZNWUGYST-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-5-(difluoromethyl)-4-methyl-1,2,4-triazol-3-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(N(C)C(C(F)F)=N2)=O)=C1F AFAIUVZNWUGYST-UHFFFAOYSA-N 0.000 description 2
BMSUYKMKXWIQJS-UHFFFAOYSA-N 2-chloro-2,2-difluoroethanimidamide Chemical compound NC(=N)C(F)(F)Cl BMSUYKMKXWIQJS-UHFFFAOYSA-N 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical class COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
241000207894 Convolvulus arvensis Species 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
235000003403 Limnocharis flava Nutrition 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 2
125000003302 alkenyloxy group Chemical group 0.000 description 2
125000005133 alkynyloxy group Chemical group 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
229940125833 compound 23 Drugs 0.000 description 2
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000428 dust Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
208000037824 growth disorder Diseases 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000004970 halomethyl group Chemical group 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
230000009526 moderate injury Effects 0.000 description 2
UHQBAQFARGJRMF-UHFFFAOYSA-N n'-(2,4-dichloro-5-propan-2-yloxyanilino)-2,2,2-trifluoroethanimidamide Chemical compound CC(C)OC1=CC(N\N=C(/N)C(F)(F)F)=C(Cl)C=C1Cl UHQBAQFARGJRMF-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
WWCNXHYRAKUQDB-UHFFFAOYSA-N oxolan-3-yl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1COCC1 WWCNXHYRAKUQDB-UHFFFAOYSA-N 0.000 description 2
238000003359 percent control normalization Methods 0.000 description 2
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 2
229940067157 phenylhydrazine Drugs 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
229940035044 sorbitan monolaurate Drugs 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000009834 vaporization Methods 0.000 description 2
230000008016 vaporization Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000004562 water dispersible granule Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
238000009736 wetting Methods 0.000 description 2
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CVAWKJKISIPBOD-UHFFFAOYSA-N tert-butyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OC(C)(C)C CVAWKJKISIPBOD-UHFFFAOYSA-N 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical group 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

CA000499759A 1985-02-04 1986-01-17 Haloalkyltriazolinones Expired CA1281724C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US69761985A	1985-02-04	1985-02-04
US697,619		1985-02-04

Publications (1)

Publication Number	Publication Date
CA1281724C true CA1281724C (fr)	1991-03-19

Family

ID=24801847

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000499759A Expired CA1281724C (fr)	1985-02-04	1986-01-17	Haloalkyltriazolinones

Country Status (4)

Country	Link
EP (1)	EP0221083A1 (fr)
AU (1)	AU5358886A (fr)
CA (1)	CA1281724C (fr)
WO (1)	WO1986004481A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU572739B2 (en) *	1985-10-26	1988-05-12	Nihon Nohyaku Co., Ltd.	1,2,4-triazolin-5-one derivatives
US5125958A (en) *	1988-08-31	1992-06-30	Fmc Corporation	Herbicidal triazolinones
CA1331463C (fr) *	1988-08-31	1994-08-16	Kathleen Megan Poss	Triazolinones herbicides
DE4303676A1 (de) *	1993-02-09	1994-08-11	Bayer Ag	1-Aryltriazolin(thi)one
DE4309966A1 (de) *	1993-03-26	1994-09-29	Bayer Ag	Substituierte 1-Aryltriazolinone
DE19802697A1 (de)	1998-01-24	1999-07-29	Bayer Ag	Selektive Herbizide auf Basis von N-Aryl-triazolin(thi)onen und N-Arylsulfonylamino(thio)carbonyltriazolin(thi)onen

1986
- 1986-01-17 CA CA000499759A patent/CA1281724C/fr not_active Expired
- 1986-01-21 WO PCT/US1986/000111 patent/WO1986004481A2/fr not_active Ceased
- 1986-01-21 AU AU53588/86A patent/AU5358886A/en not_active Abandoned
- 1986-01-21 EP EP19860900971 patent/EP0221083A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
WO1986004481A2 (fr)	1986-08-14
AU5358886A (en)	1986-08-26
EP0221083A1 (fr)	1987-05-13

Legal Events

Date	Code	Title	Description
1993-09-21	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 19930921

Publication	Publication Date	Title
EP0432212B1 (fr)	1993-04-07	Triazolinones herbicides
EP0294375B1 (fr)	1993-08-18	Triazolinones d'aryle herbicides
EP0161304B1 (fr)	1990-01-10	1-aryl-4-substitue-1,4-dihydro-5h-tetrazol-5-ones herbicides et leurs analogues a base de soufre
AU578708B2 (en)	1988-11-03	Herbicidal 2-aryl-1,2,4-triazine-3,5(2h,4h)-diones and sulfuranalogs thereof
US5344812A (en)	1994-09-06	Herbicidal 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates
EP0199794A4 (fr)	1987-09-28	Aryl-triazolinones herbicides.
AU566839B2 (en)	1987-10-29	Herbicidal 1-aryl-2-1, 2, 4-triazolin-5-ones
CA1281724C (fr)	1991-03-19	Haloalkyltriazolinones
WO1988001133A1 (fr)	1988-02-25	Herbicides
US4894084A (en)	1990-01-16	Substituted quinolinonyl and dihydroquinolinonyl triazolinone herbicides
US4919708A (en)	1990-04-24	Haloalkyl triazolinones and herbicidal use thereof
US4818276A (en)	1989-04-04	Herbicidal 1-aryl-Δ2 -1,2,4-triazolin-5-ones
US4906284A (en)	1990-03-06	Herbicidal fluoropropyl compounds
US4909829A (en)	1990-03-20	Substituted quinolinonyl and dihydroquinolinonyl tetrazolinone herbicides
US5174809A (en)	1992-12-29	Herbicidal aryl triazolinones
US5294595A (en)	1994-03-15	Herbicidal aryl triazolinones
EP0231176A1 (fr)	1987-08-12	1-ARYL-$g(d)?2 -1,2,4-TRIAZOLINE-5-ONES HERBICIDES
US4994104A (en)	1991-02-19	Tetrahydrophthalimide carbamate herbicidal compositions