GB1601609A - 4-substituted-2-chloro-3,5-diiodo pyridines and their use as herbicides - Google Patents

4-substituted-2-chloro-3,5-diiodo pyridines and their use as herbicides Download PDF

Info

Publication number: GB1601609A
Authority: GB; United Kingdom
Prior art keywords: chloro; salt; compounds; group; methyl
Prior art date: 1977-05-04
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

GB17517/78A

Other languages

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.)

Shell Agrar GmbH and Co KG

Original Assignee

Celamerck GmbH and Co KG

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.)

1977-05-04

Filing date

1978-05-03

Publication date

1981-11-04

1978-05-03 Application filed by Celamerck GmbH and Co KG filed Critical Celamerck GmbH and Co KG

1981-11-04 Publication of GB1601609A publication Critical patent/GB1601609A/en

Status Expired legal-status Critical Current

Links

-1 4-substituted-2-chloro-3,5-diiodo pyridines Chemical class 0.000 title claims description 10
239000004009 herbicide Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 59
150000003839 salts Chemical class 0.000 claims abstract description 36
230000002363 herbicidal effect Effects 0.000 claims abstract description 12
230000026045 iodination Effects 0.000 claims abstract description 10
238000006192 iodination reaction Methods 0.000 claims abstract description 10
VBEHFOMFHUQAOW-UHFFFAOYSA-N 2-chloro-1h-pyridin-4-one Chemical compound OC1=CC=NC(Cl)=C1 VBEHFOMFHUQAOW-UHFFFAOYSA-N 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 56
239000004480 active ingredient Substances 0.000 claims description 37
238000000034 method Methods 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
DPHOWLYOBWCRKU-UHFFFAOYSA-N 2-chloro-3,5-diiodo-1H-pyridin-4-one Chemical compound ClC1=NC=C(C(=C1I)O)I DPHOWLYOBWCRKU-UHFFFAOYSA-N 0.000 claims description 13
QWZIGUJYMLBQCY-UHFFFAOYSA-N (2-chloro-3,5-diiodopyridin-4-yl) acetate Chemical compound CC(=O)OC1=C(I)C=NC(Cl)=C1I QWZIGUJYMLBQCY-UHFFFAOYSA-N 0.000 claims description 12
239000000243 solution Substances 0.000 claims description 12
150000001767 cationic compounds Chemical class 0.000 claims description 11
150000002892 organic cations Chemical class 0.000 claims description 11
GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 9
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 8
HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 8
UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
239000011630 iodine Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
YJKIALIXRCSISK-UHFFFAOYSA-N Chlorfenprop-methyl Chemical compound COC(=O)C(Cl)CC1=CC=C(Cl)C=C1 YJKIALIXRCSISK-UHFFFAOYSA-N 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 claims description 6
WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 6
BYYMILHAKOURNM-UHFFFAOYSA-N Buturon Chemical compound C#CC(C)N(C)C(=O)NC1=CC=C(Cl)C=C1 BYYMILHAKOURNM-UHFFFAOYSA-N 0.000 claims description 6
LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
KTRWHSQWLXKTDQ-UHFFFAOYSA-N 2-(2-butan-2-yl-4,6-dinitrophenyl)acetic acid Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1CC(O)=O KTRWHSQWLXKTDQ-UHFFFAOYSA-N 0.000 claims description 5
IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 claims description 5
RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 5
239000000843 powder Substances 0.000 claims description 5
XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
241000196324 Embryophyta Species 0.000 claims description 4
239000004495 emulsifiable concentrate Substances 0.000 claims description 4
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 claims description 4
NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 claims description 4
DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 claims description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
XTFNPKDYCLFGPV-OMCISZLKSA-N Bromofenoxim Chemical compound C1=C(Br)C(O)=C(Br)C=C1\C=N\OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O XTFNPKDYCLFGPV-OMCISZLKSA-N 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
238000010410 dusting Methods 0.000 claims description 3
239000003995 emulsifying agent Substances 0.000 claims description 3
SLCGUGMPSUYJAY-LBPRGKRZSA-N ethyl (2s)-2-(n-benzoyl-3,4-dichloroanilino)propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1N([C@@H](C)C(=O)OCC)C(=O)C1=CC=CC=C1 SLCGUGMPSUYJAY-LBPRGKRZSA-N 0.000 claims description 3
229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
235000011152 sodium sulphate Nutrition 0.000 claims description 3
125000005504 styryl group Chemical group 0.000 claims 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 claims description 3
TWWNLDITIRCJDN-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)naphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CC(C)C)C(CC(C)C)=CC=C21 TWWNLDITIRCJDN-UHFFFAOYSA-N 0.000 claims description 2
XNBRPBFBBCFVEH-UHFFFAOYSA-N 2-methylpropyl 2-[4-(4-chlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC(C)C)=CC=C1OC1=CC=C(Cl)C=C1 XNBRPBFBBCFVEH-UHFFFAOYSA-N 0.000 claims description 2
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical group [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000012141 concentrate Substances 0.000 claims description 2
238000010790 dilution Methods 0.000 claims description 2
239000012895 dilution Substances 0.000 claims description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical group CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 claims description 2
238000009472 formulation Methods 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
230000002083 iodinating effect Effects 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 claims description 2
125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
244000038559 crop plants Species 0.000 claims 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 3
150000002148 esters Chemical class 0.000 abstract 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000004656 dimethylamines Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
DIBXJWBRMQPMEO-UHFFFAOYSA-N (2-chloro-3,5-diiodo-6-methylpyridin-4-yl) acetate Chemical compound ClC1=NC(=C(C(=C1I)OC(C)=O)I)C DIBXJWBRMQPMEO-UHFFFAOYSA-N 0.000 description 1
ZEDSBPGXXSOTFB-UHFFFAOYSA-N (2-chloro-3,5-diiodopyridin-4-yl) N,N-dimethylcarbamate Chemical compound ClC1=NC=C(C(=C1I)OC(N(C)C)=O)I ZEDSBPGXXSOTFB-UHFFFAOYSA-N 0.000 description 1
JUJZDBFYZNHMLA-UHFFFAOYSA-N 2-(1,4-dichlorocyclohexa-2,4-dien-1-yl)oxyacetic acid Chemical compound ClC1(OCC(=O)O)CC=C(C=C1)Cl JUJZDBFYZNHMLA-UHFFFAOYSA-N 0.000 description 1
FVCKBKBSDFLXGY-UHFFFAOYSA-N 2-chloro-3,5-diiodopyridine Chemical class ClC1=NC=C(I)C=C1I FVCKBKBSDFLXGY-UHFFFAOYSA-N 0.000 description 1
RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
YONDBLQXPZYKLQ-UHFFFAOYSA-N C=CC.C=CC.C=CC.C=CC.[Na] Chemical group C=CC.C=CC.C=CC.C=CC.[Na] YONDBLQXPZYKLQ-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
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 1
241000209510 Liliopsida Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000003139 biocide Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000003947 ethylamines Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
239000001230 potassium iodate Substances 0.000 description 1
229940093930 potassium iodate Drugs 0.000 description 1
235000006666 potassium iodate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Landscapes

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

GB17517/78A 1977-05-04 1978-05-03 4-substituted-2-chloro-3,5-diiodo pyridines and their use as herbicides Expired GB1601609A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772719904 DE2719904A1 (de)	1977-05-04	1977-05-04	Neue pyridinderivate, ihre herstellung und verwendung

Publications (1)

Publication Number	Publication Date
GB1601609A true GB1601609A (en)	1981-11-04

Family

ID=6007986

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
GB17517/78A Expired GB1601609A (en)	1977-05-04	1978-05-03	4-substituted-2-chloro-3,5-diiodo pyridines and their use as herbicides

Country Status (28)

Country	Link
JP (1)	JPS53137968A (es)
AR (1)	AR222012A1 (es)
AT (1)	AT364191B (es)
AU (1)	AU518477B2 (es)
BE (1)	BE866699A (es)
BR (1)	BR7802751A (es)
CA (1)	CA1096383A (es)
CH (1)	CH638788A5 (es)
DE (1)	DE2719904A1 (es)
DK (1)	DK193478A (es)
ES (2)	ES469387A1 (es)
FR (1)	FR2389607B1 (es)
GB (1)	GB1601609A (es)
GR (1)	GR64825B (es)
HU (1)	HU182008B (es)
IE (1)	IE46876B1 (es)
IL (1)	IL54625A (es)
IT (1)	IT1103860B (es)
LU (1)	LU79582A1 (es)
MX (1)	MX5292E (es)
NL (1)	NL7804747A (es)
NZ (1)	NZ187160A (es)
PL (1)	PL110684B1 (es)
SE (1)	SE7805138L (es)
SU (1)	SU1047376A3 (es)
TR (1)	TR20611A (es)
YU (1)	YU99078A (es)
ZA (1)	ZA782544B (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PL398871A1 (pl)	2012-04-18	2013-10-28	Bio Technology Spólka Z Ograniczona Odpowiedzialnoscia	Sposób otrzymywania nawozu mineralno-organicznego z odpadów pofermentacyjnych w biogazowniach rolniczych
PL398870A1 (pl)	2012-04-18	2013-10-28	Biosynergia Spólka Akcyjna	Nawóz i sposób otrzymywania zawiesinowego nawozu fosforowo-organicznego z odpadów pofermentacyjnych

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1242057A (en) *	1968-07-04	1971-08-11	Ici Ltd	Derivatives of 4-hydroxytetrafluoropyridine and the use thereof as plant growth regulators
GB1241869A (en) *	1969-02-25	1971-08-04	Ici Ltd	Process for making a halopyridine
IL44846A0 (en) *	1973-05-24	1974-07-31	Ici Ltd	Herbicidal pyridine derivatives

1977
- 1977-05-04 DE DE19772719904 patent/DE2719904A1/de not_active Withdrawn
1978
- 1978-04-24 GR GR56074A patent/GR64825B/el unknown
- 1978-04-25 AT AT0295578A patent/AT364191B/de not_active IP Right Cessation
- 1978-04-25 YU YU00990/78A patent/YU99078A/xx unknown
- 1978-04-27 TR TR20611A patent/TR20611A/xx unknown
- 1978-04-28 AR AR271981A patent/AR222012A1/es active
- 1978-05-02 IT IT49163/78A patent/IT1103860B/it active
- 1978-05-02 IL IL54625A patent/IL54625A/xx unknown
- 1978-05-02 CH CH476478A patent/CH638788A5/de not_active IP Right Cessation
- 1978-05-02 JP JP5326378A patent/JPS53137968A/ja active Pending
- 1978-05-03 SU SU782609553A patent/SU1047376A3/ru active
- 1978-05-03 ES ES469387A patent/ES469387A1/es not_active Expired
- 1978-05-03 NL NL7804747A patent/NL7804747A/xx not_active Application Discontinuation
- 1978-05-03 HU HU78CE1164A patent/HU182008B/hu unknown
- 1978-05-03 LU LU79582A patent/LU79582A1/de unknown
- 1978-05-03 PL PL1978206550A patent/PL110684B1/pl unknown
- 1978-05-03 NZ NZ187160A patent/NZ187160A/xx unknown
- 1978-05-03 BE BE187389A patent/BE866699A/xx not_active IP Right Cessation
- 1978-05-03 FR FR7813184A patent/FR2389607B1/fr not_active Expired
- 1978-05-03 SE SE7805138A patent/SE7805138L/xx unknown
- 1978-05-03 BR BR7802751A patent/BR7802751A/pt unknown
- 1978-05-03 GB GB17517/78A patent/GB1601609A/en not_active Expired
- 1978-05-03 ZA ZA782544A patent/ZA782544B/xx unknown
- 1978-05-03 MX MX787057U patent/MX5292E/es unknown
- 1978-05-03 CA CA302,519A patent/CA1096383A/en not_active Expired
- 1978-05-03 DK DK193478A patent/DK193478A/da unknown
- 1978-05-03 AU AU35727/78A patent/AU518477B2/en not_active Expired
- 1978-05-03 IE IE893/78A patent/IE46876B1/en unknown
- 1978-10-06 ES ES474005A patent/ES474005A1/es not_active Expired

Also Published As

Publication number	Publication date
SU1047376A3 (ru)	1983-10-07
AU518477B2 (en)	1981-10-01
ATA295578A (de)	1981-02-15
BR7802751A (pt)	1979-04-10
MX5292E (es)	1983-06-06
IE46876B1 (en)	1983-10-19
FR2389607B1 (es)	1983-06-17
HU182008B (en)	1983-12-28
IL54625A0 (en)	1978-07-31
NZ187160A (en)	1981-03-16
BE866699A (fr)	1978-11-03
ES469387A1 (es)	1978-12-01
YU99078A (en)	1983-01-21
CA1096383A (en)	1981-02-24
CH638788A5 (en)	1983-10-14
LU79582A1 (de)	1979-06-13
GR64825B (en)	1980-06-03
NL7804747A (nl)	1978-11-07
JPS53137968A (en)	1978-12-01
AT364191B (de)	1981-09-25
PL110684B1 (en)	1980-07-31
IT1103860B (it)	1985-10-14
DE2719904A1 (de)	1978-11-09
TR20611A (tr)	1982-01-01
AU3572778A (en)	1979-11-08
IT7849163A0 (it)	1978-05-02
ES474005A1 (es)	1979-05-01
SE7805138L (sv)	1978-11-05
ZA782544B (en)	1980-01-30
AR222012A1 (es)	1981-04-15
PL206550A1 (pl)	1979-04-09
FR2389607A1 (es)	1978-12-01
IL54625A (en)	1981-09-13
IE780893L (en)	1978-11-04
DK193478A (da)	1978-11-05

Publication	Publication Date	Title
DE69128804T2 (de)	1998-05-14	Herbizide Carboxamidderivate
DE69402689T2 (de)	1997-07-31	4-Benzoyl-Isoxazol Derivate, deren Herstellung und deren Verwendung als Herbizide
EP0363818B1 (de)	1994-04-06	Oximether-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide
DE69126825T2 (de)	1998-02-19	Substituierte Phthalide und heterozyklische Phthalide
DD200969A5 (de)	1983-06-29	Herbizide mittel
DE2812571A1 (de)	1979-02-01	4-(5-fluormethyl-2-pyridyloxy)- phenoxyalkancarbonsaeuren und deren derivate, herbicide, die diese verbindungen enthalten, und verfahren zur unkrautbekaempfung unter verwendung der herbicide
EP0003890A2 (en)	1979-09-05	Herbicidal pyridine compounds and herbicidal compositions containing them
DD272069A5 (de)	1989-09-27	Herstellung von (r)-2-[4-(5-chlor-3-flourpyridin-2-yloxy)-phenoxyl]-propionsaeurepropinylester mit herbizider wirkung
US4235621A (en)	1980-11-25	2-Substituted phenoxy-3-chloro-5-trifluoromethyl pyridine useful as a herbicide
US4149872A (en)	1979-04-17	N-pyridinyl urea and cyclopropanecarboxamide herbicides
US4033754A (en)	1977-07-05	Substituted cyclohexene esters
EP0075840B1 (de)	1987-11-11	Heterocyclische Phenyläther, Verfahren zu deren Herstellung und diese enthaltende herbizide Mittel
CA1096383A (en)	1981-02-24	Pyridine derivatives, their production and use
EP0086375B1 (de)	1986-04-09	Pyridinderivate, ihre Herstellung und Verwendung
JPH0122266B2 (es)	1989-04-25
US4453972A (en)	1984-06-12	Phenoxy pyridine derivatives and herbicidal compositions containing same
EP0171724A2 (de)	1986-02-19	Phenoxypropionsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
EP0010692A1 (de)	1980-05-14	Neue m-Anilidurethane, sie enthaltende Herbizide und Verfahren zu deren Herstellung, sowie Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs
US4722749A (en)	1988-02-02	Pyridinesulfonamides and their use as herbicidal agents
CS236791B2 (en)	1985-05-15	Herbicide agent and processing method of active component
EP1034166B1 (de)	2003-05-02	Substituierte 2-phenyl-3(2h)-pyridazinone
FR2555579A1 (fr)	1985-05-31	Nouveaux derives de pyridylacetonitriles, leur preparation et leur utilisation comme antifongiques dans le domaine agricole
CH676596A5 (es)	1991-02-15
DD254317A5 (de)	1988-02-24	Herbizide und wachstumsregulierende mittel
EP0086477A1 (de)	1983-08-24	Neue Chloracetanilide, Verfahren zu ihrer Herstellung, ihre Verwendung als Herbizide und sie enthaltende Mittel

Legal Events

Date	Code	Title	Description
1982-01-27	PS	Patent sealed [section 19, patents act 1949]
1985-01-09	PCNP	Patent ceased through non-payment of renewal fee