NO753099L - - Google Patents

Info

Publication number: NO753099L
Authority: NO; Norway
Prior art keywords: thiadiazol; pyrimidinone; tetrahydro; alkyl; methyl
Prior art date: 1974-09-11

Application number

NO753099A

Other languages

English (en)

Norwegian (no)

Inventor

J Krenzer

Original Assignee

Velsicol Chemical 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.)

1974-09-11

Filing date

1975-09-10

Publication date

1976-03-12

1974-09-11 Priority claimed from US05/505,118 external-priority patent/US3979388A/en

1975-05-27 Priority claimed from US05/580,636 external-priority patent/US4006009A/en

1975-07-10 Priority claimed from US05/594,932 external-priority patent/US4004912A/en

1975-09-10 Application filed by Velsicol Chemical Corp filed Critical Velsicol Chemical Corp

1976-03-12 Publication of NO753099L publication Critical patent/NO753099L/no

Links

150000001875 compounds Chemical class 0.000 claims description 56
238000002360 preparation method Methods 0.000 claims description 56
238000006243 chemical reaction Methods 0.000 claims description 51
238000010992 reflux Methods 0.000 claims description 47
241000196324 Embryophyta Species 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 26
-1 Thiadiazole compound Chemical class 0.000 claims description 24
230000002363 herbicidal effect Effects 0.000 claims description 21
125000001188 haloalkyl group Chemical group 0.000 claims description 18
125000003342 alkenyl group Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 8
150000008064 anhydrides Chemical class 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
239000012429 reaction media Substances 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 6
OVAAROARWYHXPN-UHFFFAOYSA-N 4-hydroxy-1-methyl-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-1,3-diazinan-2-one Chemical group O=C1N(C)CCC(O)N1C1=NN=C(C(F)(F)F)S1 OVAAROARWYHXPN-UHFFFAOYSA-N 0.000 claims description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
239000012430 organic reaction media Substances 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
231100000331 toxic Toxicity 0.000 claims description 4
230000002588 toxic effect Effects 0.000 claims description 4
KCHYNHBKOZBLQJ-UHFFFAOYSA-N 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-hydroxy-1-methyl-1,3-diazinan-2-one Chemical compound O=C1N(C)CCC(O)N1C1=NN=C(C(C)(C)C)S1 KCHYNHBKOZBLQJ-UHFFFAOYSA-N 0.000 claims description 3
AWQGVMHYDKFROX-UHFFFAOYSA-N [1-methyl-2-oxo-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-1,3-diazinan-4-yl] acetate Chemical group O=C1N(C)CCC(OC(C)=O)N1C1=NN=C(C(F)(F)F)S1 AWQGVMHYDKFROX-UHFFFAOYSA-N 0.000 claims description 3
ISGNQTVYHROXAT-UHFFFAOYSA-N [1-methyl-2-oxo-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-1,3-diazinan-4-yl] benzoate Chemical group FC(C1=NN=C(S1)N1C(N(CCC1OC(C1=CC=CC=C1)=O)C)=O)(F)F ISGNQTVYHROXAT-UHFFFAOYSA-N 0.000 claims description 3
IIYLCOQNDYYSHI-UHFFFAOYSA-N [3-(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-propyl-1,3-diazinan-4-yl] butanoate Chemical group O=C1N(CCC)CCC(OC(=O)CCC)N1C1=NN=C(SC)S1 IIYLCOQNDYYSHI-UHFFFAOYSA-N 0.000 claims description 3
ZDHDLIMIBWXQTB-UHFFFAOYSA-N [3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] acetate Chemical group O=C1N(C)CCC(OC(C)=O)N1C1=NN=C(C(C)(C)C)S1 ZDHDLIMIBWXQTB-UHFFFAOYSA-N 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000004615 ingredient Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims 3
125000004093 cyano group Chemical group *C#N 0.000 claims 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
IJZGFAHHROHFIF-UHFFFAOYSA-N [3-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-prop-2-ynyl-1,3-diazinan-4-yl] benzoate Chemical group S1C(S(=O)C)=NN=C1N1C(=O)N(CC#C)CCC1OC(=O)C1=CC=CC=C1 IJZGFAHHROHFIF-UHFFFAOYSA-N 0.000 claims 1
239000011541 reaction mixture Substances 0.000 description 77
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
239000000047 product Substances 0.000 description 42
239000011521 glass Substances 0.000 description 35
239000002244 precipitate Substances 0.000 description 35
239000000203 mixture Substances 0.000 description 33
238000003756 stirring Methods 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000706 filtrate Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 8
229910001873 dinitrogen Inorganic materials 0.000 description 8
239000004009 herbicide Substances 0.000 description 8
239000012047 saturated solution Substances 0.000 description 8
239000002002 slurry Substances 0.000 description 8
239000007787 solid Substances 0.000 description 7
241001290610 Abildgaardia Species 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012265 solid product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
SWJVFAOGXDGTCX-UHFFFAOYSA-N 2-cyanoethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCC#N SWJVFAOGXDGTCX-UHFFFAOYSA-N 0.000 description 5
150000001241 acetals Chemical class 0.000 description 5
230000006378 damage Effects 0.000 description 5
239000000428 dust Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
UIOXNNAWANDJCZ-UHFFFAOYSA-N 1,1-dimethoxypropane Chemical compound CCC(OC)OC UIOXNNAWANDJCZ-UHFFFAOYSA-N 0.000 description 3
JUPUBWHBHDEZIX-UHFFFAOYSA-N 2-cyclopropyl-5-isocyanato-1,3,4-thiadiazole Chemical class S1C(N=C=O)=NN=C1C1CC1 JUPUBWHBHDEZIX-UHFFFAOYSA-N 0.000 description 3
LJGUQVJJWFWIBA-UHFFFAOYSA-N 2-isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical class FC(F)(F)C1=NN=C(N=C=O)S1 LJGUQVJJWFWIBA-UHFFFAOYSA-N 0.000 description 3
LPTCOWQQRGJMNE-UHFFFAOYSA-N 2-isocyanato-5-methoxy-1,3,4-thiadiazole Chemical class COC1=NN=C(N=C=O)S1 LPTCOWQQRGJMNE-UHFFFAOYSA-N 0.000 description 3
RRLBNHGOAVKNNB-UHFFFAOYSA-N 2-isocyanato-5-methyl-1,3,4-thiadiazole Chemical class CC1=NN=C(N=C=O)S1 RRLBNHGOAVKNNB-UHFFFAOYSA-N 0.000 description 3
DAURFRNOXYUHFB-UHFFFAOYSA-N 2-isocyanato-5-methylsulfanyl-1,3,4-thiadiazole Chemical class CSC1=NN=C(N=C=O)S1 DAURFRNOXYUHFB-UHFFFAOYSA-N 0.000 description 3
QYOSQYFLNBXVKF-UHFFFAOYSA-N 2-isocyanato-5-methylsulfonyl-1,3,4-thiadiazole Chemical class CS(=O)(=O)C1=NN=C(N=C=O)S1 QYOSQYFLNBXVKF-UHFFFAOYSA-N 0.000 description 3
TWAUUVMXSRYMPA-UHFFFAOYSA-N 2-tert-butyl-5-isocyanato-1,3,4-thiadiazole Chemical class CC(C)(C)C1=NN=C(N=C=O)S1 TWAUUVMXSRYMPA-UHFFFAOYSA-N 0.000 description 3
FRNBQLDGXCGOTH-UHFFFAOYSA-N 3,3-dimethoxy-n-methylpropan-1-amine Chemical compound CNCCC(OC)OC FRNBQLDGXCGOTH-UHFFFAOYSA-N 0.000 description 3
SIVRIOHWGDOMNB-UHFFFAOYSA-N 3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-4-hydroxy-1-prop-2-ynyl-1,3-diazinan-2-one Chemical compound OC1CCN(CC#C)C(=O)N1C1=NN=C(C2CC2)S1 SIVRIOHWGDOMNB-UHFFFAOYSA-N 0.000 description 3
QYNUDMYVEAVPQD-UHFFFAOYSA-N 4-hydroxy-3-(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)-1-propyl-1,3-diazinan-2-one Chemical compound O=C1N(CCC)CCC(O)N1C1=NN=C(SC)S1 QYNUDMYVEAVPQD-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000004965 chloroalkyl group Chemical group 0.000 description 3
239000000539 dimer Substances 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
XOIYUDRMTQZUOZ-UHFFFAOYSA-N n-ethyl-3,3-dimethoxypropan-1-amine Chemical compound CCNCCC(OC)OC XOIYUDRMTQZUOZ-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 3
150000004867 thiadiazoles Chemical class 0.000 description 3
244000045561 useful plants Species 0.000 description 3
LEIMMJJENBPWPK-UHFFFAOYSA-N 1-ethyl-4-hydroxy-3-(5-methoxy-1,3,4-thiadiazol-2-yl)-1,3-diazinan-2-one Chemical compound O=C1N(CC)CCC(O)N1C1=NN=C(OC)S1 LEIMMJJENBPWPK-UHFFFAOYSA-N 0.000 description 2
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
TUAFOYVYXNSXRH-UHFFFAOYSA-N 3,3-dimethoxy-n-prop-2-ynylpropan-1-amine Chemical compound COC(OC)CCNCC#C TUAFOYVYXNSXRH-UHFFFAOYSA-N 0.000 description 2
IZTWTTYZZGKEKO-UHFFFAOYSA-N 4-hydroxy-1-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3-diazinan-2-one Chemical compound O=C1N(C)CCC(O)N1C1=NN=C(C)S1 IZTWTTYZZGKEKO-UHFFFAOYSA-N 0.000 description 2
LTEUXHSAYOSFGQ-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(F)(F)F)S1 LTEUXHSAYOSFGQ-UHFFFAOYSA-N 0.000 description 2
AVLUMBXGKFNNAS-UHFFFAOYSA-N 5-cyclopropyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CC1 AVLUMBXGKFNNAS-UHFFFAOYSA-N 0.000 description 2
DRHLSQJZTGPDMP-UHFFFAOYSA-N 5-methoxy-1,3,4-thiadiazol-2-amine Chemical compound COC1=NN=C(N)S1 DRHLSQJZTGPDMP-UHFFFAOYSA-N 0.000 description 2
HMPUHXCGUHDVBI-UHFFFAOYSA-N 5-methyl-1,3,4-thiadiazol-2-amine Chemical compound CC1=NN=C(N)S1 HMPUHXCGUHDVBI-UHFFFAOYSA-N 0.000 description 2
PCLAZAJARAIGGD-UHFFFAOYSA-N 5-methylsulfanyl-1,3,4-thiadiazol-2-amine Chemical compound CSC1=NN=C(N)S1 PCLAZAJARAIGGD-UHFFFAOYSA-N 0.000 description 2
GXPKJOYKJDOUKX-UHFFFAOYSA-N 5-methylsulfonyl-1,3,4-thiadiazol-2-amine Chemical compound CS(=O)(=O)C1=NN=C(N)S1 GXPKJOYKJDOUKX-UHFFFAOYSA-N 0.000 description 2
ICXDPEFCLDSXLI-UHFFFAOYSA-N 5-tert-butyl-1,3,4-thiadiazol-2-amine Chemical compound CC(C)(C)C1=NN=C(N)S1 ICXDPEFCLDSXLI-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
235000005637 Brassica campestris Nutrition 0.000 description 2
240000008100 Brassica rapa Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241000132536 Cirsium Species 0.000 description 2
240000004153 Hibiscus sabdariffa Species 0.000 description 2
235000001018 Hibiscus sabdariffa Nutrition 0.000 description 2
241000209082 Lolium Species 0.000 description 2
244000236458 Panicum colonum Species 0.000 description 2
235000015225 Panicum colonum Nutrition 0.000 description 2
244000292697 Polygonum aviculare Species 0.000 description 2
235000006386 Polygonum aviculare Nutrition 0.000 description 2
235000002357 Ribes grossularia Nutrition 0.000 description 2
244000171263 Ribes grossularia Species 0.000 description 2
235000005291 Rumex acetosa Nutrition 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
YHXLMBAWSJESHD-UHFFFAOYSA-N [3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-prop-2-ynyl-1,3-diazinan-4-yl] benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCN(CC#C)C(=O)N1C(S1)=NN=C1C1CC1 YHXLMBAWSJESHD-UHFFFAOYSA-N 0.000 description 2
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230000001070 adhesive effect Effects 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
JOHUAELJNSBTGS-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(=O)C1CCCCC1 JOHUAELJNSBTGS-UHFFFAOYSA-N 0.000 description 2
239000002274 desiccant Substances 0.000 description 2
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239000007788 liquid Substances 0.000 description 2
244000144972 livestock Species 0.000 description 2
239000002245 particle Substances 0.000 description 2
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
208000037974 severe injury Diseases 0.000 description 2
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241000894007 species Species 0.000 description 2
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239000000126 substance Substances 0.000 description 2
FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 1
PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
PEHFQQWAINXOQG-UHFFFAOYSA-N (2-methoxyacetyl) 2-methoxyacetate Chemical compound COCC(=O)OC(=O)COC PEHFQQWAINXOQG-UHFFFAOYSA-N 0.000 description 1
NLWILHIIFVRCSH-UHFFFAOYSA-N (3,4,5-trichlorobenzoyl) 3,4,5-trichlorobenzoate Chemical compound ClC1=C(Cl)C(Cl)=CC(C(=O)OC(=O)C=2C=C(Cl)C(Cl)=C(Cl)C=2)=C1 NLWILHIIFVRCSH-UHFFFAOYSA-N 0.000 description 1
DZJZPASJHDOOQA-UHFFFAOYSA-N (3-bromobenzoyl) 3-bromobenzoate Chemical compound BrC1=CC=CC(C(=O)OC(=O)C=2C=C(Br)C=CC=2)=C1 DZJZPASJHDOOQA-UHFFFAOYSA-N 0.000 description 1
MWUSAETYTBNPDG-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OC(=O)C1=CC=C(Cl)C=C1 MWUSAETYTBNPDG-UHFFFAOYSA-N 0.000 description 1
GLPAOYCUUFPDQJ-UHFFFAOYSA-N (4-ethoxybenzoyl) 4-ethoxybenzoate Chemical compound C1=CC(OCC)=CC=C1C(=O)OC(=O)C1=CC=C(OCC)C=C1 GLPAOYCUUFPDQJ-UHFFFAOYSA-N 0.000 description 1
BBLXFRIGTQYGOT-UHFFFAOYSA-N (4-fluorobenzoyl) 4-fluorobenzoate Chemical compound C1=CC(F)=CC=C1C(=O)OC(=O)C1=CC=C(F)C=C1 BBLXFRIGTQYGOT-UHFFFAOYSA-N 0.000 description 1
YGMHIBLUWGDWKP-UHFFFAOYSA-N (4-methoxybenzoyl) 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC(=O)C1=CC=C(OC)C=C1 YGMHIBLUWGDWKP-UHFFFAOYSA-N 0.000 description 1
QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 description 1
VWJYDONMXDIHNY-NSCUHMNNSA-N (e)-pent-3-en-1-amine Chemical compound C\C=C\CCN VWJYDONMXDIHNY-NSCUHMNNSA-N 0.000 description 1
GFUOIQFPJDKRCI-UHFFFAOYSA-N 1,1-dimethoxybutan-2-amine Chemical compound CCC(N)C(OC)OC GFUOIQFPJDKRCI-UHFFFAOYSA-N 0.000 description 1
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239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
230000009526 moderate injury Effects 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
IRILZLKKSNFQHA-UHFFFAOYSA-N o-[3-[5-(bromomethyl)-1,3,4-thiadiazol-2-yl]-1-methyl-2-oxo-1,3-diazinan-4-yl] 4-methylbenzenecarbothioate Chemical compound N=1N=C(CBr)SC=1N1C(=O)N(C)CCC1OC(=S)C1=CC=C(C)C=C1 IRILZLKKSNFQHA-UHFFFAOYSA-N 0.000 description 1
UVBBCQLPTZEDHT-UHFFFAOYSA-N pent-4-en-1-amine Chemical compound NCCCC=C UVBBCQLPTZEDHT-UHFFFAOYSA-N 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
229940100684 pentylamine Drugs 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
235000009736 ragweed Nutrition 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
201000010153 skin papilloma Diseases 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000012747 synergistic agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
235000005765 wild carrot Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

NO753099A 1974-09-11 1975-09-10 NO753099L (xx)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US05/505,118 US3979388A (en)	1974-09-11	1974-09-11	Thiadiazolyltetrahydropyrimidinones
US05/580,636 US4006009A (en)	1975-05-27	1975-05-27	1-Thiadiazolyl-6-acyloxytetrahydropyrimidinone herbicides
US05/594,932 US4004912A (en)	1975-07-10	1975-07-10	1-Thiadiazolyl-6-acyloxytetrahydropyrimidinone herbicides

Publications (1)

Publication Number	Publication Date
NO753099L true NO753099L (xx)	1976-03-12

Family

ID=27414276

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO753099A NO753099L (xx)	1974-09-11	1975-09-10

Country Status (17)

Country	Link
JP (1)	JPS5826724B2 (xx)
AR (1)	AR219690A1 (xx)
AT (1)	AT344700B (xx)
BR (1)	BR7505773A (xx)
CA (1)	CA1049522A (xx)
CH (1)	CH614443A5 (xx)
DE (1)	DE2540366A1 (xx)
DK (1)	DK404275A (xx)
ES (1)	ES440841A1 (xx)
FR (1)	FR2284605A1 (xx)
GB (1)	GB1510133A (xx)
IL (1)	IL47960A (xx)
IT (1)	IT1046966B (xx)
NL (1)	NL7510653A (xx)
NO (1)	NO753099L (xx)
SE (1)	SE7510083L (xx)
YU (1)	YU39948B (xx)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2018391579A1 (en)	2017-12-19	2020-08-06	Bayer Aktiengesellschaft	Substituted N-heterocyclyl- and N-heteroaryl-tetrahydropyrimidinones and the salts thereof, and the use of same as herbicidal active substances

1975
- 1975-08-20 IL IL47960A patent/IL47960A/xx unknown
- 1975-09-04 AR AR260261A patent/AR219690A1/es active
- 1975-09-05 CH CH1152175A patent/CH614443A5/xx not_active IP Right Cessation
- 1975-09-09 BR BR7505773A patent/BR7505773A/pt unknown
- 1975-09-09 CA CA235,106A patent/CA1049522A/en not_active Expired
- 1975-09-10 DK DK404275A patent/DK404275A/da unknown
- 1975-09-10 NL NL7510653A patent/NL7510653A/xx not_active Application Discontinuation
- 1975-09-10 AT AT699375A patent/AT344700B/de not_active IP Right Cessation
- 1975-09-10 IT IT51281/75A patent/IT1046966B/it active
- 1975-09-10 ES ES440841A patent/ES440841A1/es not_active Expired
- 1975-09-10 YU YU2282/75A patent/YU39948B/xx unknown
- 1975-09-10 DE DE19752540366 patent/DE2540366A1/de not_active Ceased
- 1975-09-10 NO NO753099A patent/NO753099L/no unknown
- 1975-09-10 GB GB37193/75A patent/GB1510133A/en not_active Expired
- 1975-09-10 SE SE7510083A patent/SE7510083L/xx unknown
- 1975-09-11 FR FR7527937A patent/FR2284605A1/fr active Granted
- 1975-09-11 JP JP50110439A patent/JPS5826724B2/ja not_active Expired

Also Published As

Publication number	Publication date
GB1510133A (en)	1978-05-10
JPS5826724B2 (ja)	1983-06-04
FR2284605A1 (fr)	1976-04-09
IL47960A0 (en)	1975-11-25
DK404275A (da)	1976-03-12
AU8395775A (en)	1977-02-17
SE7510083L (sv)	1976-03-12
AR219690A1 (es)	1980-09-15
ATA699375A (de)	1977-12-15
YU228275A (en)	1982-05-31
DE2540366A1 (de)	1976-03-25
ES440841A1 (es)	1977-07-01
IL47960A (en)	1978-09-29
IT1046966B (it)	1980-09-10
FR2284605B1 (xx)	1980-04-04
BR7505773A (pt)	1976-08-31
CH614443A5 (en)	1979-11-30
YU39948B (en)	1985-06-30
JPS5154926A (en)	1976-05-14
NL7510653A (nl)	1976-03-15
AT344700B (de)	1978-08-10
CA1049522A (en)	1979-02-27

Publication	Publication Date	Title
KR850001951B1 (ko)	1985-12-31	N-아릴벤즈아미드 유도체의 제조방법
JPH0143751B2 (xx)	1989-09-22
US4979982A (en)	1990-12-25	Herbicidal cinnamic ester uracils
US4175081A (en)	1979-11-20	5-Substituted thiadiazole ureas
NO752680L (xx)	1976-02-06
IE47724B1 (en)	1984-05-30	Herbicidally active 1,2,4-oxadiazole derivatives,a process for their manufacture and their use
JPS60158185A (ja)	1985-08-19	５‐ハロゲノアルキル‐１，３，４‐チアジアゾール‐２‐イルオキシアセトアミド類
US4338449A (en)	1982-07-06	Herbicidal thiadiazolines
PL114534B1 (en)	1981-02-28	Herbicide
NO753099L (xx)	1976-03-12
US4182712A (en)	1980-01-08	5-Substituted thiadiazole ureas
US4066436A (en)	1978-01-03	Method of controlling sicklepod in soybeans
NO753861L (xx)	1976-10-15
CA1057291A (en)	1979-06-26	5-cyanoalkyl-1,3,4-thiadiazole-2-ylureas
US3981714A (en)	1976-09-21	Cyclic N-thiadiazolyl-(2)-carboxylic acid compounds and herbicidal compositions
US3972706A (en)	1976-08-03	Herbicidal method
KR810000003B1 (ko)	1981-01-31	1-티아디아졸릴-6-아씰록시 테트라 하이드로 피리미딘온의 제조방법
US3900484A (en)	1975-08-19	1,2,3,5-oxathiadiazolin-4-one,2-oxides
NO140382B (no)	1979-05-14	Tiadiazolylimidazolidinoner med herbicid virkning
US4404017A (en)	1983-09-13	Phthalimidoguanidine plant growth regulators
GB2111996A (en)	1983-07-13	Herbicidal derivatives of tetrahydrobenzothiazole
US3959301A (en)	1976-05-25	Algicidol 2-chloro-5-tolyl-1,3,4-thiadiazoles
US3944409A (en)	1976-03-16	Method of increasing the yield of plants having storage organs by treatment with thiadiazolylimidazolines
CA1081701A (en)	1980-07-15	3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines and method of combating undesired plant growth
JPS5810386B2 (ja)	1983-02-25	新規なチアジアゾリルイミダゾリジノン類の製造方法